CA2094785A1 - Peptide chelatant le metal - Google Patents

Peptide chelatant le metal

Info

Publication number: CA2094785A1
Authority: CA; Canada
Prior art keywords: peptide; metal chelating; amino; mcp; coupling
Prior art date: 1992-05-08
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

CA 2094785

Other languages

English (en)

Inventor

Jean Gariepy

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.)

Ontario Cancer Institute

Original Assignee

Individual

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.)

1992-05-08

Filing date

1993-04-23

Publication date

1993-11-09

1993-04-23 Application filed by Individual filed Critical Individual

1993-11-09 Publication of CA2094785A1 publication Critical patent/CA2094785A1/fr

Status Abandoned legal-status Critical Current

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 59
229910052751 metal Inorganic materials 0.000 title claims abstract description 28
239000002184 metal Substances 0.000 title claims abstract description 28
230000008878 coupling Effects 0.000 claims abstract description 21
238000010168 coupling process Methods 0.000 claims abstract description 21
238000005859 coupling reaction Methods 0.000 claims abstract description 21
230000008685 targeting Effects 0.000 claims abstract description 18
125000003277 amino group Chemical group 0.000 claims description 12
239000004472 Lysine Substances 0.000 claims description 8
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical class NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 claims description 6
150000003573 thiols Chemical class 0.000 claims description 5
239000003446 ligand Substances 0.000 claims description 4
ATAFDSCDEDHMOK-UHFFFAOYSA-N 3,3-diaminopropanoic acid Chemical compound NC(N)CC(O)=O ATAFDSCDEDHMOK-UHFFFAOYSA-N 0.000 claims description 3
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 3
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 3
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 3
229960003104 ornithine Drugs 0.000 claims description 3
HBMHOTNDCRKENP-UHFFFAOYSA-N 3-amino-1-isothiocyanatopyrrole-2,5-dione Chemical class NC=1C(=O)N(C(C1)=O)N=C=S HBMHOTNDCRKENP-UHFFFAOYSA-N 0.000 claims description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical group NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
125000001433 C-terminal amino-acid group Chemical group 0.000 claims 4
125000000539 amino acid group Chemical group 0.000 claims 4
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
ZWZOCUWOXSDYFZ-CQDKDKBSSA-N Tyr-Ala-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 ZWZOCUWOXSDYFZ-CQDKDKBSSA-N 0.000 claims 1
150000001540 azides Chemical class 0.000 claims 1
235000018417 cysteine Nutrition 0.000 claims 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
239000011347 resin Substances 0.000 description 14
229920005989 resin Polymers 0.000 description 14
239000003795 chemical substances by application Substances 0.000 description 12
102000004196 processed proteins & peptides Human genes 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
235000001014 amino acid Nutrition 0.000 description 9
150000001413 amino acids Chemical class 0.000 description 9
239000000427 antigen Substances 0.000 description 8
102000036639 antigens Human genes 0.000 description 8
108091007433 antigens Proteins 0.000 description 8
206010028980 Neoplasm Diseases 0.000 description 7
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000010276 construction Methods 0.000 description 6
239000012634 fragment Substances 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
229940051022 radioimmunoconjugate Drugs 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
125000003396 thiol group Chemical group [H]S* 0.000 description 5
101710121996 Hexon protein p72 Proteins 0.000 description 4
101710125418 Major capsid protein Proteins 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
239000002738 chelating agent Substances 0.000 description 4
238000002523 gelfiltration Methods 0.000 description 4
229940127121 immunoconjugate Drugs 0.000 description 4
235000018977 lysine Nutrition 0.000 description 4
238000000034 method Methods 0.000 description 4
230000037361 pathway Effects 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
DIYPCWKHSODVAP-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)benzoyl]oxy-2,5-dioxopyrrolidine-3-sulfonic acid Chemical compound O=C1C(S(=O)(=O)O)CC(=O)N1OC(=O)C1=CC=CC(N2C(C=CC2=O)=O)=C1 DIYPCWKHSODVAP-UHFFFAOYSA-N 0.000 description 3
229920005654 Sephadex Polymers 0.000 description 3
239000012507 Sephadex™ Substances 0.000 description 3
238000013459 approach Methods 0.000 description 3
125000000837 carbohydrate group Chemical group 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
230000009920 chelation Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000021615 conjugation Effects 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
229910021645 metal ion Inorganic materials 0.000 description 3
-1 or 1 Chemical compound 0.000 description 3
238000010647 peptide synthesis reaction Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000007790 solid phase Substances 0.000 description 3
125000006850 spacer group Chemical group 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
239000004971 Cross linker Substances 0.000 description 2
150000008574 D-amino acids Chemical class 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
125000003172 aldehyde group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002372 labelling Methods 0.000 description 2
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
230000008569 process Effects 0.000 description 2
230000002285 radioactive effect Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
RWQRRDGPIMBJMY-UHFFFAOYSA-N 2-acetamido-4-sulfanylbutanoic acid;hydrazine Chemical compound NN.CC(=O)NC(C(O)=O)CCS RWQRRDGPIMBJMY-UHFFFAOYSA-N 0.000 description 1
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 1
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
108010001857 Cell Surface Receptors Proteins 0.000 description 1
KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
241000828585 Gari Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
102000003886 Glycoproteins Human genes 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
102000008394 Immunoglobulin Fragments Human genes 0.000 description 1
108010021625 Immunoglobulin Fragments Proteins 0.000 description 1
235000019766 L-Lysine Nutrition 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
102000008072 Lymphokines Human genes 0.000 description 1
108010074338 Lymphokines Proteins 0.000 description 1
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
108091034117 Oligonucleotide Proteins 0.000 description 1
108010039918 Polylysine Proteins 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
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 1
235000004279 alanine Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000012538 ammonium bicarbonate Nutrition 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003302 anti-idiotype Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
230000010056 antibody-dependent cellular cytotoxicity Effects 0.000 description 1
230000000890 antigenic effect Effects 0.000 description 1
239000012062 aqueous buffer Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
239000008366 buffered solution Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002771 cell marker Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
238000002405 diagnostic procedure Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001493 electron microscopy Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
210000004408 hybridoma Anatomy 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
230000007233 immunological mechanism Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
150000002668 lysine derivatives Chemical class 0.000 description 1
238000002595 magnetic resonance imaging Methods 0.000 description 1
125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
102000006240 membrane receptors Human genes 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000005298 paramagnetic effect Effects 0.000 description 1
229960003330 pentetic acid Drugs 0.000 description 1
239000000813 peptide hormone Substances 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
238000012360 testing method Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000012800 visualization Methods 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
- 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
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Immunology (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Biomedical Technology (AREA)
Biochemistry (AREA)
Hematology (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Cell Biology (AREA)
Biotechnology (AREA)
Biophysics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Microbiology (AREA)
Genetics & Genomics (AREA)
Food Science & Technology (AREA)
Physics & Mathematics (AREA)
Analytical Chemistry (AREA)
General Physics & Mathematics (AREA)
Pathology (AREA)
Peptides Or Proteins (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

CA 2094785 1992-05-08 1993-04-23 Peptide chelatant le metal Abandoned CA2094785A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US88069192A	1992-05-08	1992-05-08
US880,691		1992-05-08

Publications (1)

Publication Number	Publication Date
CA2094785A1 true CA2094785A1 (fr)	1993-11-09

Family

ID=25376852

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2094785 Abandoned CA2094785A1 (fr)	1992-05-08	1993-04-23	Peptide chelatant le metal

Country Status (2)

Country	Link
CA (1)	CA2094785A1 (fr)
WO (1)	WO1993023425A1 (fr)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5674977A (en) *	1993-02-05	1997-10-07	The Ontario Cancer Institute	Branched synthetic peptide conjugate
US6071699A (en)	1996-06-07	2000-06-06	California Institute Of Technology	Nucleic acid mediated electron transfer
US5952172A (en)	1993-12-10	1999-09-14	California Institute Of Technology	Nucleic acid mediated electron transfer
US5591578A (en) *	1993-12-10	1997-01-07	California Institute Of Technology	Nucleic acid mediated electron transfer
US5824473A (en)	1993-12-10	1998-10-20	California Institute Of Technology	Nucleic acid mediated electron transfer
US6444423B1 (en)	1996-06-07	2002-09-03	Molecular Dynamics, Inc.	Nucleosides comprising polydentate ligands
AU738189B2 (en) *	1996-06-07	2001-09-13	Ge Healthcare (Sv) Corp.	Nucleic acid mediated electron transfer
US7381525B1 (en)	1997-03-07	2008-06-03	Clinical Micro Sensors, Inc.	AC/DC voltage apparatus for detection of nucleic acids
US7045285B1 (en)	1996-11-05	2006-05-16	Clinical Micro Sensors, Inc.	Electronic transfer moieties attached to peptide nucleic acids
US7014992B1 (en) *	1996-11-05	2006-03-21	Clinical Micro Sensors, Inc.	Conductive oligomers attached to electrodes and nucleoside analogs
US7160678B1 (en)	1996-11-05	2007-01-09	Clinical Micro Sensors, Inc.	Compositions for the electronic detection of analytes utilizing monolayers
US7393645B2 (en)	1996-11-05	2008-07-01	Clinical Micro Sensors, Inc.	Compositions for the electronic detection of analytes utilizing monolayers
US6096273A (en)	1996-11-05	2000-08-01	Clinical Micro Sensors	Electrodes linked via conductive oligomers to nucleic acids
US6013459A (en)	1997-06-12	2000-01-11	Clinical Micro Sensors, Inc.	Detection of analytes using reorganization energy
WO1999037819A2 (fr)	1998-01-27	1999-07-29	Clinical Micro Sensors, Inc.	Amplification des acides nucleiques par detection electronique
US6761816B1 (en)	1998-06-23	2004-07-13	Clinical Micro Systems, Inc.	Printed circuit boards with monolayers and capture ligands
US6290839B1 (en)	1998-06-23	2001-09-18	Clinical Micro Sensors, Inc.	Systems for electrophoretic transport and detection of analytes
US7087148B1 (en)	1998-06-23	2006-08-08	Clinical Micro Sensors, Inc.	Binding acceleration techniques for the detection of analytes
US6740518B1 (en)	1998-09-17	2004-05-25	Clinical Micro Sensors, Inc.	Signal detection techniques for the detection of analytes
AU1241000A (en)	1998-10-27	2000-05-15	Clinical Micro Sensors, Inc.	Detection of target analytes using particles and electrodes
US6833267B1 (en)	1998-12-30	2004-12-21	Clinical Micro Sensors, Inc.	Tissue collection devices containing biosensors
US7312087B2 (en)	2000-01-11	2007-12-25	Clinical Micro Sensors, Inc.	Devices and methods for biochip multiplexing
US6942771B1 (en)	1999-04-21	2005-09-13	Clinical Micro Sensors, Inc.	Microfluidic systems in the electrochemical detection of target analytes
KR20100075503A (ko)	1999-10-01	2010-07-02	디엠아이 바이오사이언시스, 인크	금속 결합 화합물 및 그의 용도
US7632803B2 (en)	1999-10-01	2009-12-15	Dmi Life Sciences, Inc.	Metal-binding compounds and uses therefor
US7592304B2 (en)	1999-10-01	2009-09-22	Dmi Life Sciences, Inc.	Metal-binding compounds and uses therefor
CA2575768C (fr) *	2004-06-28	2012-12-04	Japan Science And Technology Agency	Methode de criblage d'un peptide de neutralisation de toxine, d'un peptide inhibant la toxine stx2 et d'un agent de neutralisation d'une verotoxine
ITMI20061607A1 (it) *	2006-08-09	2008-02-10	Maria Vincenza Carriero	Peptidi con attivita farmacologica
CN114106108B (zh) *	2021-11-25	2023-07-14	中国石油大学(华东)	一种多肽-金纳米颗粒复合物、其制备方法及应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69018226T2 (de) *	1989-07-20	1995-09-21	Sandoz-Patent-Gmbh, 79539 Loerrach	Markierte polypeptidderivate.
FR2652004B1 (fr) *	1989-09-21	1994-10-28	Immunotech Partners	Nouveaux derives hydrophiles, application au diagnostic et a la therapeutique, kits diagnostiques ou therapeutiques et reactifs immunologiques.
ATE152917T1 (de) *	1990-09-28	1997-05-15	Neorx Corp	Polymere träger zur freisetzung kovalent gebundener wirkstoffe

1993
- 1993-04-23 CA CA 2094785 patent/CA2094785A1/fr not_active Abandoned
- 1993-05-07 WO PCT/CA1993/000207 patent/WO1993023425A1/fr not_active Ceased

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1995-10-23	FZDE	Dead

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