CA2542512A1 - Nanocomposites d'hydrogel pour applications ophtalmiques - Google Patents

Nanocomposites d'hydrogel pour applications ophtalmiques Download PDF

Info

Publication number: CA2542512A1
Authority: CA; Canada
Prior art keywords: hydrogel; nanoparticles; copolymer; solution; reversible
Prior art date: 2003-09-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002542512A

Other languages

English (en)

Inventor

Nathan Ravi

Aliyar H. Ali

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

US Department of Veterans Affairs

Washington University in St Louis WUSTL

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-09-04

Filing date

2004-09-03

Publication date

2005-03-17

2003-11-13 Priority claimed from US10/706,081 external-priority patent/US8192485B2/en

2004-09-03 Application filed by US Department of Veterans Affairs, Washington University in St Louis WUSTL filed Critical US Department of Veterans Affairs

2005-03-17 Publication of CA2542512A1 publication Critical patent/CA2542512A1/fr

Status Abandoned legal-status Critical Current

Links

239000000017 hydrogel Substances 0.000 title claims abstract description 207
229920001577 copolymer Polymers 0.000 claims abstract description 130
239000002105 nanoparticle Substances 0.000 claims abstract description 99
229920000642 polymer Polymers 0.000 claims abstract description 77
230000002441 reversible effect Effects 0.000 claims abstract description 52
239000002114 nanocomposite Substances 0.000 claims abstract description 50
230000002829 reductive effect Effects 0.000 claims abstract description 31
238000000034 method Methods 0.000 claims description 79
239000000178 monomer Substances 0.000 claims description 40
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 36
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 30
238000001879 gelation Methods 0.000 claims description 29
239000004971 Cross linker Substances 0.000 claims description 28
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 22
230000009467 reduction Effects 0.000 claims description 22
238000007254 oxidation reaction Methods 0.000 claims description 21
230000003647 oxidation Effects 0.000 claims description 20
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 19
239000002245 particle Substances 0.000 claims description 19
239000002202 Polyethylene glycol Substances 0.000 claims description 18
238000004132 cross linking Methods 0.000 claims description 18
229920001223 polyethylene glycol Polymers 0.000 claims description 18
239000000377 silicon dioxide Substances 0.000 claims description 18
238000006116 polymerization reaction Methods 0.000 claims description 17
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 16
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 16
229910052737 gold Inorganic materials 0.000 claims description 16
239000010931 gold Substances 0.000 claims description 16
-1 cinnamoyl Chemical class 0.000 claims description 15
150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 15
108090000623 proteins and genes Proteins 0.000 claims description 15
102000004169 proteins and genes Human genes 0.000 claims description 15
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000003638 chemical reducing agent Substances 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 claims description 13
239000000919 ceramic Substances 0.000 claims description 12
229910052709 silver Inorganic materials 0.000 claims description 12
239000004332 silver Substances 0.000 claims description 12
229910052723 transition metal Inorganic materials 0.000 claims description 12
150000003624 transition metals Chemical class 0.000 claims description 12
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
238000011065 in-situ storage Methods 0.000 claims description 11
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 claims description 10
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 10
239000006185 dispersion Substances 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 8
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 7
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 7
AXZIZCRDJHHCAS-UHFFFAOYSA-N 2-methylidene-4-methylsulfanylbutanamide Chemical compound CSCCC(=C)C(N)=O AXZIZCRDJHHCAS-UHFFFAOYSA-N 0.000 claims description 7
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 7
125000000751 azo group Chemical class [*]N=N[*] 0.000 claims description 7
125000004386 diacrylate group Chemical group 0.000 claims description 7
230000002209 hydrophobic effect Effects 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
150000002739 metals Chemical class 0.000 claims description 7
IPGRTXQKFZCLJS-UHFFFAOYSA-N n-(2-hydroxypropyl)prop-2-enamide Chemical compound CC(O)CNC(=O)C=C IPGRTXQKFZCLJS-UHFFFAOYSA-N 0.000 claims description 7
DJVKJGIZQFBFGS-UHFFFAOYSA-N n-[2-[2-(prop-2-enoylamino)ethyldisulfanyl]ethyl]prop-2-enamide Chemical group C=CC(=O)NCCSSCCNC(=O)C=C DJVKJGIZQFBFGS-UHFFFAOYSA-N 0.000 claims description 7
229960003104 ornithine Drugs 0.000 claims description 7
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 7
229920002554 vinyl polymer Polymers 0.000 claims description 7
TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 claims description 6
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 6
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical class C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 6
WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 6
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 6
229920005862 polyol Polymers 0.000 claims description 6
150000003077 polyols Chemical class 0.000 claims description 6
AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 claims description 5
238000007865 diluting Methods 0.000 claims description 5
239000002151 riboflavin Substances 0.000 claims description 5
229960002477 riboflavin Drugs 0.000 claims description 5
235000019192 riboflavin Nutrition 0.000 claims description 5
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
238000005406 washing Methods 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 2
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 claims description 2
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims description 2
238000004108 freeze drying Methods 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
AEBNPEXFDZBTIB-UHFFFAOYSA-N 2-methyl-4-phenylbut-2-enamide Chemical compound NC(=O)C(C)=CCC1=CC=CC=C1 AEBNPEXFDZBTIB-UHFFFAOYSA-N 0.000 claims 2
125000000129 anionic group Chemical group 0.000 claims 1
125000002091 cationic group Chemical group 0.000 claims 1
239000002082 metal nanoparticle Substances 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 94
239000000499 gel Substances 0.000 description 63
210000000695 crystalline len Anatomy 0.000 description 59
YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 30
150000003573 thiols Chemical class 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000000463 material Substances 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
210000001508 eye Anatomy 0.000 description 21
238000002360 preparation method Methods 0.000 description 21
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
239000000203 mixture Substances 0.000 description 16
229920002401 polyacrylamide Polymers 0.000 description 14
238000001356 surgical procedure Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
208000002177 Cataract Diseases 0.000 description 11
238000002474 experimental method Methods 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
230000004308 accommodation Effects 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
230000001419 dependent effect Effects 0.000 description 8
238000009826 distribution Methods 0.000 description 7
239000003999 initiator Substances 0.000 description 7
239000002923 metal particle Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 6
230000008859 change Effects 0.000 description 6
238000012512 characterization method Methods 0.000 description 6
239000002131 composite material Substances 0.000 description 6
230000004438 eyesight Effects 0.000 description 6
239000011521 glass Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
230000034005 thiol-disulfide exchange Effects 0.000 description 6
108091003079 Bovine Serum Albumin Proteins 0.000 description 5
230000009102 absorption Effects 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
229940098773 bovine serum albumin Drugs 0.000 description 5
238000007334 copolymerization reaction Methods 0.000 description 5
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 5
239000011159 matrix material Substances 0.000 description 5
238000005259 measurement Methods 0.000 description 5
229920001296 polysiloxane Polymers 0.000 description 5
238000003756 stirring Methods 0.000 description 5
231100000331 toxic Toxicity 0.000 description 5
230000002588 toxic effect Effects 0.000 description 5
231100000419 toxicity Toxicity 0.000 description 5
230000001988 toxicity Effects 0.000 description 5
238000001069 Raman spectroscopy Methods 0.000 description 4
OWMVSZAMULFTJU-UHFFFAOYSA-N bis-tris Chemical compound OCCN(CCO)C(CO)(CO)CO OWMVSZAMULFTJU-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
230000003068 static effect Effects 0.000 description 4
150000003926 acrylamides Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000000872 buffer Substances 0.000 description 3
210000004087 cornea Anatomy 0.000 description 3
230000008034 disappearance Effects 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000009977 dual effect Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
201000010041 presbyopia Diseases 0.000 description 3
210000001525 retina Anatomy 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
125000003396 thiol group Chemical group [H]S* 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical class OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
238000001237 Raman spectrum Methods 0.000 description 2
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
229910001870 ammonium persulfate Inorganic materials 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
238000010382 chemical cross-linking Methods 0.000 description 2
239000003431 cross linking reagent Substances 0.000 description 2
OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 2
229940099500 cystamine Drugs 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
230000003993 interaction Effects 0.000 description 2
230000007774 longterm Effects 0.000 description 2
208000001491 myopia Diseases 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
238000010526 radical polymerization reaction Methods 0.000 description 2
239000012966 redox initiator Substances 0.000 description 2
208000014733 refractive error Diseases 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
238000005063 solubilization Methods 0.000 description 2
230000007928 solubilization Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
235000021286 stilbenes Nutrition 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical class CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
CMAFCINQNNFLLM-UHFFFAOYSA-N (1-hydroperoxy-2-methylpropyl)benzene Chemical compound CC(C)C(OO)C1=CC=CC=C1 CMAFCINQNNFLLM-UHFFFAOYSA-N 0.000 description 1
HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
HSOOIVBINKDISP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CCC)OC(=O)C(C)=C HSOOIVBINKDISP-UHFFFAOYSA-N 0.000 description 1
KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 description 1
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
BXAAQNFGSQKPDZ-UHFFFAOYSA-N 3-[1,2,2-tris(prop-2-enoxy)ethoxy]prop-1-ene Chemical compound C=CCOC(OCC=C)C(OCC=C)OCC=C BXAAQNFGSQKPDZ-UHFFFAOYSA-N 0.000 description 1
PBVAJRFEEOIAGW-UHFFFAOYSA-N 3-[bis(2-carboxyethyl)phosphanyl]propanoic acid;hydrochloride Chemical compound Cl.OC(=O)CCP(CCC(O)=O)CCC(O)=O PBVAJRFEEOIAGW-UHFFFAOYSA-N 0.000 description 1
AEKLLKXWNJVXKT-UHFFFAOYSA-N 3-thiophen-2-ylprop-2-enamide Chemical compound NC(=O)C=CC1=CC=CS1 AEKLLKXWNJVXKT-UHFFFAOYSA-N 0.000 description 1
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
102000014824 Crystallins Human genes 0.000 description 1
108010064003 Crystallins Proteins 0.000 description 1
229920002871 Dammar gum Polymers 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000000232 Lipid Bilayer Substances 0.000 description 1
238000006845 Michael addition reaction Methods 0.000 description 1
HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
101710138657 Neurotoxin Proteins 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
206010034972 Photosensitivity reaction Diseases 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
206010036346 Posterior capsule opacification Diseases 0.000 description 1
241000288906 Primates Species 0.000 description 1
239000012506 Sephacryl® Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
229920006328 Styrofoam Polymers 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
PZBFGYYEXUXCOF-UHFFFAOYSA-N TCEP Chemical compound OC(=O)CCP(CCC(O)=O)CCC(O)=O PZBFGYYEXUXCOF-UHFFFAOYSA-N 0.000 description 1
206010047513 Vision blurred Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002350 accommodative effect Effects 0.000 description 1
JEAIVVDKUUARLF-UHFFFAOYSA-N acetyloxycarbonylperoxycarbonyl acetate Chemical compound CC(=O)OC(=O)OOC(=O)OC(C)=O JEAIVVDKUUARLF-UHFFFAOYSA-N 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
238000013459 approach Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000000149 argon plasma sintering Methods 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000004323 axial length Effects 0.000 description 1
JZQAAQZDDMEFGZ-UHFFFAOYSA-N bis(ethenyl) hexanedioate Chemical compound C=COC(=O)CCCCC(=O)OC=C JZQAAQZDDMEFGZ-UHFFFAOYSA-N 0.000 description 1
ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
238000006664 bond formation reaction Methods 0.000 description 1
210000005252 bulbus oculi Anatomy 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
231100000357 carcinogen Toxicity 0.000 description 1
239000003183 carcinogenic agent Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
231100000481 chemical toxicant Toxicity 0.000 description 1
231100000045 chemical toxicity Toxicity 0.000 description 1
239000000571 coke Substances 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical class CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
125000002228 disulfide group Chemical group 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000012634 fragment Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000008570 general process Effects 0.000 description 1
230000004313 glare Effects 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
HRSYDNWBOIDHSF-UHFFFAOYSA-N hydrogen peroxide;2-(2-hydroxyethyldisulfanyl)ethanol Chemical compound OO.OCCSSCCO HRSYDNWBOIDHSF-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000014674 injury Diseases 0.000 description 1
230000009878 intermolecular interaction Effects 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002483 medication Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229960003151 mercaptamine Drugs 0.000 description 1
VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004379 myopia Effects 0.000 description 1
239000002581 neurotoxin Substances 0.000 description 1
231100000618 neurotoxin Toxicity 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
150000004978 peroxycarbonates Chemical class 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical class OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 description 1
238000007539 photo-oxidation reaction Methods 0.000 description 1
208000007578 phototoxic dermatitis Diseases 0.000 description 1
231100000018 phototoxicity Toxicity 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
MVCPDOUDYOUTKS-UHFFFAOYSA-N propanedithioic acid Chemical compound CCC(S)=S MVCPDOUDYOUTKS-UHFFFAOYSA-N 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
238000002407 reforming Methods 0.000 description 1
230000027756 respiratory electron transport chain Effects 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
210000003786 sclera Anatomy 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000010008 shearing Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
238000003307 slaughter Methods 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001370 static light scattering Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000008261 styrofoam Substances 0.000 description 1
229940035718 sular Drugs 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003104 tissue culture media Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
238000013519 translation Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/52—Hydrogels or hydrocolloids

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Oral & Maxillofacial Surgery (AREA)
Transplantation (AREA)
Epidemiology (AREA)
Dispersion Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Dermatology (AREA)
Veterinary Medicine (AREA)
Materials For Medical Uses (AREA)
Compositions Of Macromolecular Compounds (AREA)
Prostheses (AREA)
Medicinal Preparation (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA002542512A 2003-09-04 2004-09-03 Nanocomposites d'hydrogel pour applications ophtalmiques Abandoned CA2542512A1 (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
US49988703P	2003-09-04	2003-09-04
US60/499,887		2003-09-04
US10/706,081 US8192485B2 (en)	2002-11-13	2003-11-13	Reversible hydrogel systems and methods therefor
US10/706,081		2003-11-13
US56459204P	2004-04-23	2004-04-23
US60/564,592		2004-04-23
PCT/US2004/028637 WO2005023331A2 (fr)	2003-09-04	2004-09-03	Nanocomposites d'hydrogel pour applications ophtalmiques

Publications (1)

Publication Number	Publication Date
CA2542512A1 true CA2542512A1 (fr)	2005-03-17

Family

ID=34279817

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002542512A Abandoned CA2542512A1 (fr)	2003-09-04	2004-09-03	Nanocomposites d'hydrogel pour applications ophtalmiques

Country Status (4)

Country	Link
EP (1)	EP1660153A2 (fr)
JP (2)	JP4988345B2 (fr)
CA (1)	CA2542512A1 (fr)
WO (1)	WO2005023331A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN112646069A (zh) *	2020-12-15	2021-04-13	内蒙古民族大学	一种氮化碳复合水凝胶及其制备方法和应用

Families Citing this family (70)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7473738B2 (en) *	2004-09-30	2009-01-06	Johnson & Johnson Vision Care, Inc.	Lactam polymer derivatives
JP4879554B2 (ja) *	2005-10-21	2012-02-22	株式会社メニコン	ポストインプリント可能なヒドロゲル材料の製造方法
JP4974533B2 (ja) *	2006-01-30	2012-07-11	富士フイルム株式会社	ジスルフィド架橋したタンパク質ナノ粒子
SG174010A1 (en)	2006-05-03	2011-09-29	Vision Crc Ltd	Eye treatment
CN101721349B (zh) *	2008-10-16	2011-07-20	常州百瑞吉生物医药有限公司	可注射原位交联水凝胶及其制备方法和用途
US9347059B2 (en)	2011-04-25	2016-05-24	Bio-Rad Laboratories, Inc.	Methods and compositions for nucleic acid analysis
US10752949B2 (en)	2012-08-14	2020-08-25	10X Genomics, Inc.	Methods and systems for processing polynucleotides
US10273541B2 (en)	2012-08-14	2019-04-30	10X Genomics, Inc.	Methods and systems for processing polynucleotides
US10221442B2 (en)	2012-08-14	2019-03-05	10X Genomics, Inc.	Compositions and methods for sample processing
CA3216609C (fr)	2012-08-14	2024-05-14	10X Genomics, Inc.	Compositions de microcapsule et procedes
US9701998B2 (en)	2012-12-14	2017-07-11	10X Genomics, Inc.	Methods and systems for processing polynucleotides
US20240376519A1 (en) *	2012-08-14	2024-11-14	10X Genomics, Inc.	Compositions and methods for sample processing
US11591637B2 (en) *	2012-08-14	2023-02-28	10X Genomics, Inc.	Compositions and methods for sample processing
US10584381B2 (en)	2012-08-14	2020-03-10	10X Genomics, Inc.	Methods and systems for processing polynucleotides
US10323279B2 (en)	2012-08-14	2019-06-18	10X Genomics, Inc.	Methods and systems for processing polynucleotides
US9951386B2 (en)	2014-06-26	2018-04-24	10X Genomics, Inc.	Methods and systems for processing polynucleotides
WO2014093676A1 (fr)	2012-12-14	2014-06-19	10X Technologies, Inc.	Procédés et systèmes pour le traitement de polynucléotides
US10533221B2 (en)	2012-12-14	2020-01-14	10X Genomics, Inc.	Methods and systems for processing polynucleotides
AU2014214682B2 (en)	2013-02-08	2018-07-26	10X Genomics, Inc.	Polynucleotide barcode generation
US9486311B2 (en)	2013-02-14	2016-11-08	Shifamed Holdings, Llc	Hydrophilic AIOL with bonding
US10195018B2 (en)	2013-03-21	2019-02-05	Shifamed Holdings, Llc	Accommodating intraocular lens
CA3193600A1 (fr)	2013-03-21	2014-09-25	Shifamed Holdings, Llc	Mise en place de lentille intraoculaire
US10395758B2 (en)	2013-08-30	2019-08-27	10X Genomics, Inc.	Sequencing methods
US9824068B2 (en)	2013-12-16	2017-11-21	10X Genomics, Inc.	Methods and apparatus for sorting data
US10178950B2 (en) *	2013-12-20	2019-01-15	Novartis Ag	Imaging probes and associated devices, systems, and methods utilizing an elastomeric optical element
JP6427811B2 (ja) *	2014-03-20	2018-11-28	国立大学法人愛媛大学	タンパク質の保存方法
WO2015157567A1 (fr)	2014-04-10	2015-10-15	10X Genomics, Inc.	Dispositifs fluidiques, systèmes et procédés permettant d'encapsuler et de séparer des réactifs, et leurs applications
CN113249435B (zh)	2014-06-26	2024-09-03	10X基因组学有限公司	分析来自单个细胞或细胞群体的核酸的方法
US12312640B2 (en)	2014-06-26	2025-05-27	10X Genomics, Inc.	Analysis of nucleic acid sequences
JP2017526046A (ja)	2014-06-26	2017-09-07	１０エックスゲノミクス，インコーポレイテッド	核酸配列アセンブルのプロセス及びシステム
MX2016016904A (es)	2014-06-26	2017-03-27	10X Genomics Inc	Analisis de secuencias de acidos nucleicos.
AU2015306613B2 (en)	2014-08-26	2018-01-25	Shifamed Holdings, Llc	Accommodating intraocular lens
MX2017005267A (es)	2014-10-29	2017-07-26	10X Genomics Inc	Metodos y composiciones para la secuenciacion de acidos nucleicos seleccionados como diana.
US9975122B2 (en)	2014-11-05	2018-05-22	10X Genomics, Inc.	Instrument systems for integrated sample processing
SG11201705615UA (en)	2015-01-12	2017-08-30	10X Genomics Inc	Processes and systems for preparing nucleic acid sequencing libraries and libraries prepared using same
EP3245605B1 (fr)	2015-01-13	2022-04-20	10X Genomics, Inc.	Systèmes et procédés de visualisation d'informations de variation structurelle et de phasage
WO2016130578A1 (fr)	2015-02-09	2016-08-18	10X Genomics, Inc.	Systèmes et procédés pour déterminer la variation structurale et la mise en phase au moyen de données d'appel de variant
EP4286516A3 (fr)	2015-02-24	2024-03-06	10X Genomics, Inc.	Procédés et systèmes de traitement de cloisonnement
BR112017018054A2 (pt)	2015-02-24	2018-07-24	10X Genomics Inc	métodos para a cobertura de sequências de ácidos nucleicos direcionadas
US11141263B2 (en)	2015-11-18	2021-10-12	Shifamed Holdings, Llc	Multi-piece accommodating intraocular lens
JP6934197B2 (ja)	2015-11-18	2021-09-15	シファメド・ホールディングス・エルエルシー	複数片の調節式眼内レンズ
SG11201804086VA (en)	2015-12-04	2018-06-28	10X Genomics Inc	Methods and compositions for nucleic acid analysis
JP6735348B2 (ja)	2016-02-11	2020-08-05	１０エックスジェノミクス，インコーポレイテッド	全ゲノム配列データのデノボアセンブリのためのシステム、方法及び媒体
WO2017197343A2 (fr)	2016-05-12	2017-11-16	10X Genomics, Inc.	Filtres microfluidiques sur puce
WO2017197338A1 (fr)	2016-05-13	2017-11-16	10X Genomics, Inc.	Systèmes microfluidiques et procédés d'utilisation
WO2018000242A1 (fr) *	2016-06-29	2018-01-04	南京大学	Application d'un matériau autoréparateur pour une utilisation en impression 3d
US10550429B2 (en)	2016-12-22	2020-02-04	10X Genomics, Inc.	Methods and systems for processing polynucleotides
US10815525B2 (en)	2016-12-22	2020-10-27	10X Genomics, Inc.	Methods and systems for processing polynucleotides
US10011872B1 (en)	2016-12-22	2018-07-03	10X Genomics, Inc.	Methods and systems for processing polynucleotides
CN120000379A (zh)	2016-12-23	2025-05-16	施菲姆德控股有限责任公司	多片式调节性人工晶状体及其制造和使用方法
US10350056B2 (en)	2016-12-23	2019-07-16	Shifamed Holdings, Llc	Multi-piece accommodating intraocular lenses and methods for making and using same
US12264411B2 (en)	2017-01-30	2025-04-01	10X Genomics, Inc.	Methods and systems for analysis
CN110214186B (zh)	2017-01-30	2023-11-24	10X基因组学有限公司	用于基于微滴的单细胞条形编码的方法和系统
EP3625715A4 (fr)	2017-05-19	2021-03-17	10X Genomics, Inc.	Systèmes et procédés d'analyse d'ensembles de données
CN109526228B (zh)	2017-05-26	2022-11-25	10X基因组学有限公司	转座酶可接近性染色质的单细胞分析
US10844372B2 (en)	2017-05-26	2020-11-24	10X Genomics, Inc.	Single cell analysis of transposase accessible chromatin
CN110996848B (zh)	2017-05-30	2023-08-04	施菲姆德控股有限责任公司	调节性人工晶状体的表面处理以及相关方法和装置
EP4205702B1 (fr)	2017-06-07	2025-09-10	Shifamed Holdings, LLC	Lentilles intraoculaires à puissance optique réglable
EP3954782A1 (fr)	2017-11-15	2022-02-16	10X Genomics, Inc.	Perles de gel fonctionnalisées
US10829815B2 (en)	2017-11-17	2020-11-10	10X Genomics, Inc.	Methods and systems for associating physical and genetic properties of biological particles
CN108276593B (zh) *	2018-01-31	2020-06-05	合肥工业大学	一种集紫外-可见-近红外光诱导的自修复纳米复合水凝胶的制备方法
CN112262218B (zh)	2018-04-06	2024-11-08	10X基因组学有限公司	用于单细胞处理中的质量控制的系统和方法
CN109351204A (zh) *	2018-09-12	2019-02-19	济南大学	一种含氟水凝胶膜的制备方法及应用
EP3996629A4 (fr)	2019-07-11	2023-08-09	Shifamed Holdings, LLC	Lentilles intraoculaires adaptatives et procédés associés
CN110403920B (zh) *	2019-08-26	2022-12-02	江苏远恒药业有限公司	一次性医用水凝胶眼贴
CN115428088A (zh)	2020-02-13	2022-12-02	10X基因组学有限公司	用于基因表达和dna染色质可及性的联合交互式可视化的系统和方法
TW202227515A (zh) *	2020-10-15	2022-07-16	日商Kj化成品股份有限公司	聚合性組成物、其聚合物、積層體、接著劑組成物、化妝品組成物、塗佈劑組成物、油墨組成物
CN117752867B (zh) *	2023-12-21	2025-03-14	大连医科大学附属第一医院	一种眼科注射用的载细胞微凝胶及其制备方法与应用
CN119081001A (zh) *	2024-08-05	2024-12-06	东华大学	一种可降解的热致物理交联的彩色水凝胶和面膜
CN119198280A (zh) *	2024-10-18	2024-12-27	福建省集力生物技术有限公司	大分子稀样的层析浓缩方法及装置

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6222754A (ja) *	1985-07-23	1987-01-30	Nippon Shokubai Kagaku Kogyo Co Ltd	Ｎ，ｎ′−ジメタクリロイルシスタミン
US6132765A (en) *	1996-04-12	2000-10-17	Uroteq Inc.	Drug delivery via therapeutic hydrogels
US6514535B2 (en) *	1999-05-21	2003-02-04	Noveon Ip Holdings Corp.	Bioadhesive hydrogels with functionalized degradable crosslinks
JP4219485B2 (ja) *	1999-05-21	2009-02-04	株式会社メニコン	光学性含水ゲルからなる眼科用材料
DE60044135D1 (de) *	1999-07-16	2010-05-20	Univ Wm Marsh Rice	Temperaturabhängiges polymer/nanohüllen-komposite für photothermische modulierte arzneimittelabgabe
JP2003504503A (ja) *	1999-07-16	2003-02-04	ウェズリージェッセンコーポレイション	熱成形可能な眼用レンズ
IL133196A0 (en) *	1999-11-29	2001-03-19	Yissum Res Dev Co	Gastroretentive controlled release pharmaceutical dosage forms
AUPR569501A0 (en) *	2001-06-14	2001-07-12	Proteome Systems Ltd	Dissolvable gels

2004
- 2004-09-03 CA CA002542512A patent/CA2542512A1/fr not_active Abandoned
- 2004-09-03 JP JP2006525445A patent/JP4988345B2/ja not_active Expired - Fee Related
- 2004-09-03 EP EP04783018A patent/EP1660153A2/fr not_active Withdrawn
- 2004-09-03 WO PCT/US2004/028637 patent/WO2005023331A2/fr not_active Ceased
2010
- 2010-12-17 JP JP2010281920A patent/JP2011063816A/ja active Pending

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN112646069A (zh) *	2020-12-15	2021-04-13	内蒙古民族大学	一种氮化碳复合水凝胶及其制备方法和应用
CN112646069B (zh) *	2020-12-15	2022-10-21	内蒙古民族大学	一种氮化碳复合水凝胶及其制备方法和应用

Also Published As

Publication number	Publication date
JP2011063816A (ja)	2011-03-31
JP4988345B2 (ja)	2012-08-01
WO2005023331A2 (fr)	2005-03-17
EP1660153A2 (fr)	2006-05-31
WO2005023331A3 (fr)	2007-05-03
JP2007517077A (ja)	2007-06-28

Legal Events

Date	Code	Title	Description
2009-06-05	FZDE	Discontinued

Publication	Publication Date	Title
US8877227B2 (en)	2014-11-04	Hydrogel nanocomposites for intraocular lens applicatons
CA2542512A1 (fr)	2005-03-17	Nanocomposites d'hydrogel pour applications ophtalmiques
US8192485B2 (en)	2012-06-05	Reversible hydrogel systems and methods therefor
Aliyar et al.	2005	Refilling of ocular lens capsule with copolymeric hydrogel containing reversible disulfide
Swindle et al.	2008	In situ formation of hydrogels as vitreous substitutes: viscoelastic comparison to porcine vitreous
US10696802B2 (en)	2020-06-30	PVA hydrogels having improved creep resistance, lubricity, and toughness
TW421600B (en)	2001-02-11	Injectable polyethylene oxide gel implant and method for production
Karayilan et al.	2021	Polymeric materials for eye surface and intraocular applications
Swindle et al.	2007	Recent advances in polymeric vitreous substitutes
US10189961B2 (en)	2019-01-29	Creep resistant, highly lubricious, tough, and ionic hydrogels including PVA-PAAMPS hydrogels
CN105593251B (zh)	2018-05-18	形状记忆聚合物眼内晶状体
TW201026752A (en)	2010-07-16	Ionic silicone hydrogels having improved hydrolytic stability
NZ506347A (en)	2003-09-26	Methods of producing intraocular lenses and materials suitable for their production
Chirila et al.	1994	Synthetic polymers as materials for artificial vitreous body: review and recent advances
CN102049067A (zh)	2011-05-11	一种可原位交联的高分子水凝胶玻璃体替代材料
Ravi et al.	2005	Hydrogel nanocomposite as a synthetic intra‐ocular lens capable of accommodation
Foster et al.	2006	Internal osmotic pressure as a mechanism of retinal attachment in a vitreous substitute
Annaka et al.	2012	Organic–inorganic nanocomposite gels as an in situ gelation biomaterial for injectable accommodative intraocular lens
Aliyar et al.	2004	Towards the development of an artificial human vitreous
JP3561740B2 (ja)	2004-09-02	生体適合性の、光学的に透明なコラーゲン基ポリマー材料およびその製造方法
Swindle-Reilly et al.	2010	Designing hydrogels as vitreous substitutes in ophthalmic surgery
Niu et al.	2009	Synthesis and characterization of acrylamide/N-vinylpyrrolidone copolymer with pendent thiol groups for ophthalmic applications
Reilly et al.	2011	Hydrogels for intraocular lenses and other ophthalmic prostheses