SK98996A3 - Bioconjugate complexes - Google Patents

Bioconjugate complexes Download PDF

Info

Publication number: SK98996A3
Authority: SK; Slovakia
Prior art keywords: bas; phenylboronic acid; group; complexes; acid
Prior art date: 1994-01-28

Application number

SK989-96A

Other languages

English (en)

Slovak (sk)

Inventor

Mark L Stolowitz

Original Assignee

Prolinx Inc

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.)

1994-01-28

Filing date

1995-01-27

Publication date

1997-02-05

1994-01-28 Priority claimed from US08/188,531 external-priority patent/US5594151A/en

1994-01-28 Priority claimed from US08/188,958 external-priority patent/US5594111A/en

1994-01-28 Priority claimed from US08/189,176 external-priority patent/US5623055A/en

1995-01-27 Application filed by Prolinx Inc filed Critical Prolinx Inc

1997-02-05 Publication of SK98996A3 publication Critical patent/SK98996A3/sk

Links

HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims abstract description 312
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 95
230000000975 bioactive effect Effects 0.000 claims abstract description 44
230000000536 complexating effect Effects 0.000 claims abstract description 40
238000000034 method Methods 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 45
239000000126 substance Substances 0.000 claims description 43
239000012867 bioactive agent Substances 0.000 claims description 39
239000008139 complexing agent Substances 0.000 claims description 38
229910052760 oxygen Inorganic materials 0.000 claims description 37
238000002360 preparation method Methods 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 31
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
239000001301 oxygen Substances 0.000 claims description 30
125000005647 linker group Chemical group 0.000 claims description 20
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
150000001408 amides Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
239000003431 cross linking reagent Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
239000004215 Carbon black (E152) Substances 0.000 claims description 10
239000004721 Polyphenylene oxide Chemical group 0.000 claims description 10
229930195733 hydrocarbon Natural products 0.000 claims description 10
229920000570 polyether Chemical group 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
230000000269 nucleophilic effect Effects 0.000 claims description 8
238000004132 cross linking Methods 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000003147 glycosyl group Chemical group 0.000 claims 1
XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 32
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 7
229910052796 boron Inorganic materials 0.000 abstract description 7
239000000047 product Substances 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 52
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
108090000623 proteins and genes Proteins 0.000 description 47
235000018102 proteins Nutrition 0.000 description 46
102000004169 proteins and genes Human genes 0.000 description 46
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
-1 haptenes Substances 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
239000007787 solid Substances 0.000 description 34
230000015572 biosynthetic process Effects 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
238000003786 synthesis reaction Methods 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
239000007864 aqueous solution Substances 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000003795 chemical substances by application Substances 0.000 description 17
239000002244 precipitate Substances 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
150000002148 esters Chemical class 0.000 description 15
238000001914 filtration Methods 0.000 description 15
125000003277 amino group Chemical group 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
210000004027 cell Anatomy 0.000 description 13
239000000203 mixture Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 13
125000003396 thiol group Chemical group [H]S* 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 12
125000004430 oxygen atom Chemical group O* 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000002202 Polyethylene glycol Substances 0.000 description 11
238000011033 desalting Methods 0.000 description 11
229920001223 polyethylene glycol Polymers 0.000 description 11
229920002521 macromolecule Polymers 0.000 description 10
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 10
238000000746 purification Methods 0.000 description 10
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 10
108090000288 Glycoproteins Proteins 0.000 description 9
102000003886 Glycoproteins Human genes 0.000 description 9
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 9
125000003172 aldehyde group Chemical group 0.000 description 9
239000000872 buffer Substances 0.000 description 9
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 8
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 8
229960004909 aminosalicylic acid Drugs 0.000 description 8
150000001720 carbohydrates Chemical class 0.000 description 8
238000000502 dialysis Methods 0.000 description 8
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
239000008188 pellet Substances 0.000 description 8
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 7
238000001514 detection method Methods 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 7
150000000180 1,2-diols Chemical class 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
108091034117 Oligonucleotide Proteins 0.000 description 6
239000002262 Schiff base Substances 0.000 description 6
150000004753 Schiff bases Chemical class 0.000 description 6
235000014633 carbohydrates Nutrition 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
238000012544 monitoring process Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
150000003141 primary amines Chemical class 0.000 description 6
230000008569 process Effects 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 description 5
WHDQRCJAQZXAAX-UHFFFAOYSA-N 4-amino-n,2-dihydroxybenzamide Chemical compound NC1=CC=C(C(=O)NO)C(O)=C1 WHDQRCJAQZXAAX-UHFFFAOYSA-N 0.000 description 5
SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000012445 acidic reagent Substances 0.000 description 5
230000004913 activation Effects 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
230000021615 conjugation Effects 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 5
229960004963 mesalazine Drugs 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
150000003573 thiols Chemical group 0.000 description 5
DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 4
150000000185 1,3-diols Chemical class 0.000 description 4
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
LKNPLDRVWHXGKZ-UHFFFAOYSA-N 3-nitro-1h-pyridine-2-thione Chemical compound [O-][N+](=O)C1=CC=CN=C1S LKNPLDRVWHXGKZ-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 4
BIJIDLWVZZPPAY-UHFFFAOYSA-N amino hypochlorite Chemical compound NOCl BIJIDLWVZZPPAY-UHFFFAOYSA-N 0.000 description 4
239000012062 aqueous buffer Substances 0.000 description 4
229960002685 biotin Drugs 0.000 description 4
239000011616 biotin Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000001965 increasing effect Effects 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
125000005544 phthalimido group Chemical group 0.000 description 4
230000009467 reduction Effects 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
239000000523 sample Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
CXCHEKCRJQRVNG-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonyl chloride Chemical compound FC(F)(F)CS(Cl)(=O)=O CXCHEKCRJQRVNG-UHFFFAOYSA-N 0.000 description 3
QHQZEEGNGSZBOL-UHFFFAOYSA-N 2-(aminomethyl)-2-(hydroxymethyl)propane-1,3-diol Chemical compound NCC(CO)(CO)CO QHQZEEGNGSZBOL-UHFFFAOYSA-N 0.000 description 3
JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 3
QWTBDIBOOIAZEF-UHFFFAOYSA-N 3-[chloro-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile Chemical compound CC(C)N(C(C)C)P(Cl)OCCC#N QWTBDIBOOIAZEF-UHFFFAOYSA-N 0.000 description 3
SVHXAKJLLKGJGC-UHFFFAOYSA-N 4-(3-boronoanilino)-4-oxobutanoic acid Chemical compound OB(O)C1=CC=CC(NC(=O)CCC(O)=O)=C1 SVHXAKJLLKGJGC-UHFFFAOYSA-N 0.000 description 3
XLKBBIACESHASR-UHFFFAOYSA-N 5-amino-2-hydroxybenzamide Chemical compound NC(=O)C1=CC(N)=CC=C1O XLKBBIACESHASR-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 3
238000012286 ELISA Assay Methods 0.000 description 3
239000004471 Glycine Substances 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
VRWRNFAUYWXDKX-UHFFFAOYSA-N [3-(2,5-dioxopyrrol-1-yl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(N2C(C=CC2=O)=O)=C1 VRWRNFAUYWXDKX-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000011324 bead Substances 0.000 description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
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NGXUUAFYUCOICP-UHFFFAOYSA-N aminometradine Chemical group CCN1C(=O)C=C(N)N(CC=C)C1=O NGXUUAFYUCOICP-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003321 amplification Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
239000002152 aqueous-organic solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical group ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000010170 biological method Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
125000000473 carbonimidoyl group Chemical group [H]\N=C(/*)* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
150000003943 catecholamines Chemical class 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000002380 cytological effect Effects 0.000 description 1
238000004163 cytometry Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
150000002009 diols Chemical group 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
125000002587 enol group Chemical group 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000000799 fusogenic effect Effects 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229960000789 guanidine hydrochloride Drugs 0.000 description 1
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
210000004408 hybridoma Anatomy 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
230000000984 immunochemical effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000001102 lavandula vera Substances 0.000 description 1
235000018219 lavender Nutrition 0.000 description 1
239000002523 lectin Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
MXUHMQZOATZRIK-UHFFFAOYSA-N methyl 5-amino-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1O MXUHMQZOATZRIK-UHFFFAOYSA-N 0.000 description 1
KYLVAMSNNZMHSX-UHFFFAOYSA-N methyl 6-bromohexanoate Chemical compound COC(=O)CCCCCBr KYLVAMSNNZMHSX-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
TXJXPZVVSLAQOQ-UHFFFAOYSA-N methyl chlorosulfanylformate Chemical compound COC(=O)SCl TXJXPZVVSLAQOQ-UHFFFAOYSA-N 0.000 description 1
LXMQEHXQPXDTDD-UHFFFAOYSA-N n,2-dihydroxy-3-sulfanylbenzamide Chemical compound ONC(=O)C1=CC=CC(S)=C1O LXMQEHXQPXDTDD-UHFFFAOYSA-N 0.000 description 1
PLQGETASNSCKLB-UHFFFAOYSA-N n,3-dihydroxy-2-phenylmethoxybenzamide Chemical compound ONC(=O)C1=CC=CC(O)=C1OCC1=CC=CC=C1 PLQGETASNSCKLB-UHFFFAOYSA-N 0.000 description 1
NPHNUCARGFSKGB-UHFFFAOYSA-N n-amino-phenylboronamidic acid Chemical compound NNB(O)C1=CC=CC=C1 NPHNUCARGFSKGB-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
238000002515 oligonucleotide synthesis Methods 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical group [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
239000002342 ribonucleoside Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229960000581 salicylamide Drugs 0.000 description 1
150000003872 salicylic acid derivatives Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
230000008685 targeting Effects 0.000 description 1
ZFQWJXFJJZUVPI-UHFFFAOYSA-N tert-butyl n-(4-aminobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCN ZFQWJXFJJZUVPI-UHFFFAOYSA-N 0.000 description 1
RVZPDKXEHIRFPM-UHFFFAOYSA-N tert-butyl n-(6-aminohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCN RVZPDKXEHIRFPM-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WGTODYJZXSJIAG-UHFFFAOYSA-N tetramethylrhodamine chloride Chemical compound [Cl-].C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C(O)=O WGTODYJZXSJIAG-UHFFFAOYSA-N 0.000 description 1
MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 description 1
CNHYKKNIIGEXAY-UHFFFAOYSA-N thiolan-2-imine Chemical compound N=C1CCCS1 CNHYKKNIIGEXAY-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Classifications

- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0207—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)4-C(=0), e.g. 'isosters', replacing two amino acids

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Immunology (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Cell Biology (AREA)
Food Science & Technology (AREA)
Biotechnology (AREA)
Biophysics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Microbiology (AREA)
Genetics & Genomics (AREA)
Crystallography & Structural Chemistry (AREA)
Physics & Mathematics (AREA)
Analytical Chemistry (AREA)
General Physics & Mathematics (AREA)
Pathology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

SK989-96A 1994-01-28 1995-01-27 Bioconjugate complexes SK98996A3 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US18846094A	1994-01-28	1994-01-28
US08/188,531 US5594151A (en)	1994-01-28	1994-01-28	Phenylboronic acid complexing reagents derived from aminosalicylic acid
US08/188,958 US5594111A (en)	1994-01-28	1994-01-28	Phenylboronic acid complexes for bioconjugate preparation
US08/189,176 US5623055A (en)	1994-01-28	1994-01-28	Phenylboronic acid complexes derived from aminosalicylic acid for bioconjugate preparation
PCT/US1995/001004 WO1995020591A1 (en)	1994-01-28	1995-01-27	Phenylboronic acid complexes

Publications (1)

Publication Number	Publication Date
SK98996A3 true SK98996A3 (en)	1997-02-05

Family

ID=27497759

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK989-96A SK98996A3 (en)	1994-01-28	1995-01-27	Bioconjugate complexes

Country Status (15)

Country	Link
EP (1)	EP0741734B1 (cs)
JP (1)	JPH09508389A (cs)
AT (1)	ATE200292T1 (cs)
AU (1)	AU702017B2 (cs)
CA (1)	CA2181252A1 (cs)
CZ (1)	CZ220196A3 (cs)
DE (1)	DE69520561T2 (cs)
DK (1)	DK0741734T3 (cs)
ES (1)	ES2158085T3 (cs)
GR (1)	GR3036119T3 (cs)
PL (1)	PL315911A1 (cs)
PT (1)	PT741734E (cs)
RU (1)	RU2202555C2 (cs)
SK (1)	SK98996A3 (cs)
WO (1)	WO1995020591A1 (cs)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5777148A (en) *	1994-01-28	1998-07-07	Prolinx, Inc.	Boronic compound complexing reagents and highly stable complexes
US5847192A (en) *	1994-01-28	1998-12-08	Prolinx, Inc.	Boronic compound complexing reagents and complexes
US5831046A (en) *	1996-08-05	1998-11-03	Prolinx, Incorporated	Boronic acid-contaning nucleic acid monomers
EP0920413B1 (en) *	1996-08-05	2002-11-13	Prolinx, Inc.	Boronic compound complexing reagents and complexes
ATE225330T1 (de) *	1996-08-05	2002-10-15	Prolinx Inc	Komplexbildner für boronverbindung und hochstabile komplexe
US6838238B1 (en)	1996-10-17	2005-01-04	Invitrogen Corporation	Morphatides: novel shape and structure libraries
FR2758560B1 (fr) *	1997-01-20	2000-02-04	Adir	Nouveaux derives d'acides aminophenylboronique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
WO1999049082A2 (en) *	1998-03-23	1999-09-30	Invitrogen Corporation	Modified nucleotides and methods useful for nucleic acid sequencing
WO2002078947A1 (en) *	2001-04-02	2002-10-10	Prolinx Incorporated	Sensor surfaces for detecting analytes
EP1921081A1 (en) *	2006-11-06	2008-05-14	Koninklijke Philips Electronics N.V.	Use of arylboronic acids in protein labelling
US20130157926A1 (en)	2010-06-18	2013-06-20	Johannes Franciscus Joseph Engbersen	Boronated polymers
US9732101B2 (en)	2012-01-18	2017-08-15	Wisconsin Alumni Research Foundation	Bioreversible boronates for delivery of molecules into cells
US9234048B2 (en)	2012-01-18	2016-01-12	Wisconsin Alumni Research Foundation	Boronate-mediated delivery of molecules into cells

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4496722A (en) *	1981-05-01	1985-01-29	The Children's Medical Center Corporation	Reporter compounds
NO890029D0 (no) *	1989-01-04	1989-01-04	Axis Research	Nye modifiserte peptider og proteiner for in vitro diagnoser (diabetes).
GB9024775D0 (en) *	1990-11-14	1991-01-02	Axis Research	Chemical compounds

1995
- 1995-01-27 CZ CZ962201A patent/CZ220196A3/cs unknown
- 1995-01-27 AT AT95909329T patent/ATE200292T1/de not_active IP Right Cessation
- 1995-01-27 RU RU96117248/04A patent/RU2202555C2/ru not_active IP Right Cessation
- 1995-01-27 DK DK95909329T patent/DK0741734T3/da active
- 1995-01-27 AU AU17324/95A patent/AU702017B2/en not_active Ceased
- 1995-01-27 PL PL95315911A patent/PL315911A1/xx unknown
- 1995-01-27 SK SK989-96A patent/SK98996A3/sk unknown
- 1995-01-27 JP JP7520146A patent/JPH09508389A/ja not_active Ceased
- 1995-01-27 WO PCT/US1995/001004 patent/WO1995020591A1/en not_active Ceased
- 1995-01-27 CA CA002181252A patent/CA2181252A1/en not_active Abandoned
- 1995-01-27 PT PT95909329T patent/PT741734E/pt unknown
- 1995-01-27 DE DE69520561T patent/DE69520561T2/de not_active Expired - Fee Related
- 1995-01-27 ES ES95909329T patent/ES2158085T3/es not_active Expired - Lifetime
- 1995-01-27 EP EP95909329A patent/EP0741734B1/en not_active Expired - Lifetime
2001
- 2001-06-27 GR GR20010400972T patent/GR3036119T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0741734B1 (en)	2001-04-04
CA2181252A1 (en)	1995-08-03
DE69520561T2 (de)	2001-09-13
PL315911A1 (en)	1996-12-09
ES2158085T3 (es)	2001-09-01
ATE200292T1 (de)	2001-04-15
AU702017B2 (en)	1999-02-11
RU2202555C2 (ru)	2003-04-20
GR3036119T3 (en)	2001-09-28
DE69520561D1 (de)	2001-05-10
AU1732495A (en)	1995-08-15
CZ220196A3 (en)	1996-12-11
DK0741734T3 (da)	2001-07-30
PT741734E (pt)	2001-09-28
WO1995020591A1 (en)	1995-08-03
EP0741734A1 (en)	1996-11-13
JPH09508389A (ja)	1997-08-26

Publication	Publication Date	Title
US5648470A (en)	1997-07-15	Phenylboronic acid complexing reagents derived from aminosalicyclic acid
US5594111A (en)	1997-01-14	Phenylboronic acid complexes for bioconjugate preparation
US5744627A (en)	1998-04-28	Boronic compound complexing reagents and complexes
JPS60252684A (ja)	1985-12-13	螢光組合せ体
US5623055A (en)	1997-04-22	Phenylboronic acid complexes derived from aminosalicylic acid for bioconjugate preparation
SK98996A3 (en)	1997-02-05	Bioconjugate complexes
US6462179B1 (en)	2002-10-08	Phenyldiboronic acid reagents and complexes
US5877297A (en)	1999-03-02	Boronic compound complexing reagents and highly stable complexes
US6156884A (en)	2000-12-05	Bifunctional boronic compound complexing reagents and complexes
CA2262451C (en)	2006-10-24	Boronic compound complexing reagents and complexes
AU784355B2 (en)	2006-03-16	1,2-Phenylenediboronic acid reagents and complexes
DE69716085T2 (de)	2003-06-12	Komplexbildner für boronverbindung und hochstabile komplexe
US5852178A (en)	1998-12-22	Phenylboronic acid complexing reagents for conjugating biologically active molecules
US5872224A (en)	1999-02-16	Boronic compound complexing reagents and highly stable complexes
US5869623A (en)	1999-02-09	Boronic compound complexing reagents and complexes