WO1998009985B1 - Peptides anti-inflammatoires et leurs utilisations - Google Patents
Peptides anti-inflammatoires et leurs utilisationsInfo
- Publication number
- WO1998009985B1 WO1998009985B1 PCT/IL1997/000295 IL9700295W WO9809985B1 WO 1998009985 B1 WO1998009985 B1 WO 1998009985B1 IL 9700295 W IL9700295 W IL 9700295W WO 9809985 B1 WO9809985 B1 WO 9809985B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- arg
- glu
- peptide
- pro
- thr
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract 60
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract 10
- 230000003110 anti-inflammatory effect Effects 0.000 title claims 15
- 125000000539 amino acid group Chemical group 0.000 claims abstract 14
- 210000002540 macrophage Anatomy 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims abstract 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract 8
- 206010061218 Inflammation Diseases 0.000 claims abstract 5
- 230000004054 inflammatory process Effects 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 4
- 210000001744 T-lymphocyte Anatomy 0.000 claims abstract 3
- 210000003169 central nervous system Anatomy 0.000 claims abstract 3
- 230000028996 humoral immune response Effects 0.000 claims abstract 3
- 230000005764 inhibitory process Effects 0.000 claims abstract 3
- 238000013508 migration Methods 0.000 claims abstract 3
- 230000005012 migration Effects 0.000 claims abstract 3
- 230000000242 pagocytic effect Effects 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- JSLGXODUIAFWCF-WDSKDSINSA-N Arg-Asn Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CC(N)=O)C(O)=O JSLGXODUIAFWCF-WDSKDSINSA-N 0.000 claims 12
- 108010004914 prolylarginine Proteins 0.000 claims 12
- WVRUNFYJIHNFKD-WDSKDSINSA-N Arg-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CCCN=C(N)N WVRUNFYJIHNFKD-WDSKDSINSA-N 0.000 claims 11
- SIFXMYAHXJGAFC-WDSKDSINSA-N Arg-Asp Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](CC(O)=O)C(O)=O SIFXMYAHXJGAFC-WDSKDSINSA-N 0.000 claims 11
- PMGDADKJMCOXHX-BQBZGAKWSA-N Arg-Gln Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](CCC(N)=O)C(O)=O PMGDADKJMCOXHX-BQBZGAKWSA-N 0.000 claims 11
- XUUXCWCKKCZEAW-YFKPBYRVSA-N Arg-Gly Chemical compound OC(=O)CNC(=O)[C@@H](N)CCCN=C(N)N XUUXCWCKKCZEAW-YFKPBYRVSA-N 0.000 claims 11
- QYLJIYOGHRGUIH-CIUDSAMLSA-N Arg-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N QYLJIYOGHRGUIH-CIUDSAMLSA-N 0.000 claims 11
- WYBVBIHNJWOLCJ-IUCAKERBSA-N Arg-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N WYBVBIHNJWOLCJ-IUCAKERBSA-N 0.000 claims 11
- JQFZHHSQMKZLRU-IUCAKERBSA-N Arg-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N JQFZHHSQMKZLRU-IUCAKERBSA-N 0.000 claims 11
- PQBHGSGQZSOLIR-RYUDHWBXSA-N Arg-Phe Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PQBHGSGQZSOLIR-RYUDHWBXSA-N 0.000 claims 11
- LQJAALCCPOTJGB-YUMQZZPRSA-N Arg-Pro Chemical compound NC(N)=NCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O LQJAALCCPOTJGB-YUMQZZPRSA-N 0.000 claims 11
- IJYZHIOOBGIINM-WDSKDSINSA-N Arg-Ser Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N IJYZHIOOBGIINM-WDSKDSINSA-N 0.000 claims 11
- XNSKSTRGQIPTSE-ACZMJKKPSA-N Arg-Thr Chemical compound C[C@@H]([C@@H](C(=O)O)NC(=O)[C@H](CCCN=C(N)N)N)O XNSKSTRGQIPTSE-ACZMJKKPSA-N 0.000 claims 11
- DAQIJMOLTMGJLO-YUMQZZPRSA-N Arg-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N DAQIJMOLTMGJLO-YUMQZZPRSA-N 0.000 claims 11
- PMGDADKJMCOXHX-UHFFFAOYSA-N L-Arginyl-L-glutamin-acetat Natural products NC(=N)NCCCC(N)C(=O)NC(CCC(N)=O)C(O)=O PMGDADKJMCOXHX-UHFFFAOYSA-N 0.000 claims 11
- HFKJBCPRWWGPEY-BQBZGAKWSA-N L-arginyl-L-glutamic acid Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(O)=O HFKJBCPRWWGPEY-BQBZGAKWSA-N 0.000 claims 11
- WYBVBIHNJWOLCJ-UHFFFAOYSA-N N-L-arginyl-L-leucine Natural products CC(C)CC(C(O)=O)NC(=O)C(N)CCCN=C(N)N WYBVBIHNJWOLCJ-UHFFFAOYSA-N 0.000 claims 11
- HMNSRTLZAJHSIK-YUMQZZPRSA-N Pro-Arg Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1 HMNSRTLZAJHSIK-YUMQZZPRSA-N 0.000 claims 11
- HYLXOQURIOCKIH-VQVTYTSYSA-N Thr-Arg Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=N HYLXOQURIOCKIH-VQVTYTSYSA-N 0.000 claims 11
- JXNRXNCCROJZFB-RYUDHWBXSA-N Tyr-Arg Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 JXNRXNCCROJZFB-RYUDHWBXSA-N 0.000 claims 11
- 108010013835 arginine glutamate Proteins 0.000 claims 11
- 108010008355 arginyl-glutamine Proteins 0.000 claims 11
- 108010062796 arginyllysine Proteins 0.000 claims 11
- 108010060035 arginylproline Proteins 0.000 claims 11
- 108010036533 arginylvaline Proteins 0.000 claims 11
- 108010053037 kyotorphin Proteins 0.000 claims 11
- 201000010099 disease Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 7
- MPZWMIIOPAPAKE-BQBZGAKWSA-N Glu-Arg Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=N MPZWMIIOPAPAKE-BQBZGAKWSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003275 alpha amino acid group Chemical group 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 108010016626 Dipeptides Proteins 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000000099 in vitro assay Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 230000028958 macrophage cytokine production Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- SITWEMZOJNKJCH-WDSKDSINSA-N Ala-Arg Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N SITWEMZOJNKJCH-WDSKDSINSA-N 0.000 claims 1
- SVBXIUDNTRTKHE-CIUDSAMLSA-N Ala-Arg-Glu Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O SVBXIUDNTRTKHE-CIUDSAMLSA-N 0.000 claims 1
- NWVVKQZOVSTDBQ-CIUDSAMLSA-N Ala-Glu-Arg Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O NWVVKQZOVSTDBQ-CIUDSAMLSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- OMLWNBVRVJYMBQ-YUMQZZPRSA-N Arg-Arg Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O OMLWNBVRVJYMBQ-YUMQZZPRSA-N 0.000 claims 1
- UXJCMQFPDWCHKX-DCAQKATOSA-N Arg-Arg-Glu Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(O)=O)C(O)=O UXJCMQFPDWCHKX-DCAQKATOSA-N 0.000 claims 1
- OSASDIVHOSJVII-WDSKDSINSA-N Arg-Cys Chemical compound SC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N OSASDIVHOSJVII-WDSKDSINSA-N 0.000 claims 1
- HPKSHFSEXICTLI-CIUDSAMLSA-N Arg-Glu-Ala Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(O)=O HPKSHFSEXICTLI-CIUDSAMLSA-N 0.000 claims 1
- QAODJPUKWNNNRP-DCAQKATOSA-N Arg-Glu-Arg Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O QAODJPUKWNNNRP-DCAQKATOSA-N 0.000 claims 1
- RKRSYHCNPFGMTA-CIUDSAMLSA-N Arg-Glu-Asn Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O RKRSYHCNPFGMTA-CIUDSAMLSA-N 0.000 claims 1
- XLWSGICNBZGYTA-CIUDSAMLSA-N Arg-Glu-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(O)=O XLWSGICNBZGYTA-CIUDSAMLSA-N 0.000 claims 1
- NYZGVTGOMPHSJW-CIUDSAMLSA-N Arg-Glu-Cys Chemical compound C(C[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CS)C(=O)O)N)CN=C(N)N NYZGVTGOMPHSJW-CIUDSAMLSA-N 0.000 claims 1
- MZRBYBIQTIKERR-GUBZILKMSA-N Arg-Glu-Gln Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O MZRBYBIQTIKERR-GUBZILKMSA-N 0.000 claims 1
- PNQWAUXQDBIJDY-GUBZILKMSA-N Arg-Glu-Glu Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(O)=O PNQWAUXQDBIJDY-GUBZILKMSA-N 0.000 claims 1
- PBSOQGZLPFVXPU-YUMQZZPRSA-N Arg-Glu-Gly Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(O)=O PBSOQGZLPFVXPU-YUMQZZPRSA-N 0.000 claims 1
- QAXCZGMLVICQKS-SRVKXCTJSA-N Arg-Glu-His Chemical compound C1=C(NC=N1)C[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCN=C(N)N)N QAXCZGMLVICQKS-SRVKXCTJSA-N 0.000 claims 1
- OHYQKYUTLIPFOX-ZPFDUUQYSA-N Arg-Glu-Ile Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(O)=O OHYQKYUTLIPFOX-ZPFDUUQYSA-N 0.000 claims 1
- NKBQZKVMKJJDLX-SRVKXCTJSA-N Arg-Glu-Leu Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(O)=O NKBQZKVMKJJDLX-SRVKXCTJSA-N 0.000 claims 1
- OGUPCHKBOKJFMA-SRVKXCTJSA-N Arg-Glu-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N OGUPCHKBOKJFMA-SRVKXCTJSA-N 0.000 claims 1
- DJAIOAKQIOGULM-DCAQKATOSA-N Arg-Glu-Met Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCSC)C(O)=O DJAIOAKQIOGULM-DCAQKATOSA-N 0.000 claims 1
- SKTGPBFTMNLIHQ-KKUMJFAQSA-N Arg-Glu-Phe Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O SKTGPBFTMNLIHQ-KKUMJFAQSA-N 0.000 claims 1
- HPSVTWMFWCHKFN-GARJFASQSA-N Arg-Glu-Pro Chemical compound C1C[C@@H](N(C1)C(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCN=C(N)N)N)C(=O)O HPSVTWMFWCHKFN-GARJFASQSA-N 0.000 claims 1
- UFBURHXMKFQVLM-CIUDSAMLSA-N Arg-Glu-Ser Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(O)=O UFBURHXMKFQVLM-CIUDSAMLSA-N 0.000 claims 1
- NXDXECQFKHXHAM-HJGDQZAQSA-N Arg-Glu-Thr Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O NXDXECQFKHXHAM-HJGDQZAQSA-N 0.000 claims 1
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- JAYIQMNQDMOBFY-KKUMJFAQSA-N Arg-Glu-Tyr Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O JAYIQMNQDMOBFY-KKUMJFAQSA-N 0.000 claims 1
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- ROWCTNFEMKOIFQ-YUMQZZPRSA-N Arg-Met Chemical compound CSCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N ROWCTNFEMKOIFQ-YUMQZZPRSA-N 0.000 claims 1
- QADCERNTBWTXFV-JSGCOSHPSA-N Arg-Trp Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@H](CCCNC(N)=N)N)C(O)=O)=CNC2=C1 QADCERNTBWTXFV-JSGCOSHPSA-N 0.000 claims 1
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- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
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- CLDCTNHPILWQCW-CIUDSAMLSA-N Cys-Arg-Glu Chemical compound C(C[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)O)NC(=O)[C@H](CS)N)CN=C(N)N CLDCTNHPILWQCW-CIUDSAMLSA-N 0.000 claims 1
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- 201000004624 Dermatitis Diseases 0.000 claims 1
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- 208000032274 Encephalopathy Diseases 0.000 claims 1
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- VTTSANCGJWLPNC-ZPFDUUQYSA-N Glu-Arg-Ile Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(O)=O VTTSANCGJWLPNC-ZPFDUUQYSA-N 0.000 claims 1
- KKCUFHUTMKQQCF-SRVKXCTJSA-N Glu-Arg-Leu Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(O)=O KKCUFHUTMKQQCF-SRVKXCTJSA-N 0.000 claims 1
- OJGLIOXAKGFFDW-SRVKXCTJSA-N Glu-Arg-Lys Chemical compound C(CCN)C[C@@H](C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)O)N OJGLIOXAKGFFDW-SRVKXCTJSA-N 0.000 claims 1
- KEBACWCLVOXFNC-DCAQKATOSA-N Glu-Arg-Met Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(O)=O KEBACWCLVOXFNC-DCAQKATOSA-N 0.000 claims 1
- LTUVYLVIZHJCOQ-KKUMJFAQSA-N Glu-Arg-Phe Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O LTUVYLVIZHJCOQ-KKUMJFAQSA-N 0.000 claims 1
- VPKBCVUDBNINAH-GARJFASQSA-N Glu-Arg-Pro Chemical compound C1C[C@@H](N(C1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)O)N)C(=O)O VPKBCVUDBNINAH-GARJFASQSA-N 0.000 claims 1
- WOSRKEJQESVHGA-CIUDSAMLSA-N Glu-Arg-Ser Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(O)=O WOSRKEJQESVHGA-CIUDSAMLSA-N 0.000 claims 1
- SRZLHYPAOXBBSB-HJGDQZAQSA-N Glu-Arg-Thr Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(O)=O SRZLHYPAOXBBSB-HJGDQZAQSA-N 0.000 claims 1
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- DHDOADIPGZTAHT-YUMQZZPRSA-N Gly-Glu-Arg Chemical compound NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@H](C(O)=O)CCCN=C(N)N DHDOADIPGZTAHT-YUMQZZPRSA-N 0.000 claims 1
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- IMCHNUANCIGUKS-SRVKXCTJSA-N His-Glu-Arg Chemical compound [H]N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O IMCHNUANCIGUKS-SRVKXCTJSA-N 0.000 claims 1
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- FVEWRQXNISSYFO-ZPFDUUQYSA-N Ile-Arg-Glu Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N FVEWRQXNISSYFO-ZPFDUUQYSA-N 0.000 claims 1
- JDAWAWXGAUZPNJ-ZPFDUUQYSA-N Ile-Glu-Arg Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N JDAWAWXGAUZPNJ-ZPFDUUQYSA-N 0.000 claims 1
- SITWEMZOJNKJCH-UHFFFAOYSA-N L-alanine-L-arginine Natural products CC(N)C(=O)NC(C(O)=O)CCCNC(N)=N SITWEMZOJNKJCH-UHFFFAOYSA-N 0.000 claims 1
- SENJXOPIZNYLHU-UHFFFAOYSA-N L-leucyl-L-arginine Natural products CC(C)CC(N)C(=O)NC(C(O)=O)CCCN=C(N)N SENJXOPIZNYLHU-UHFFFAOYSA-N 0.000 claims 1
- SENJXOPIZNYLHU-IUCAKERBSA-N Leu-Arg Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N SENJXOPIZNYLHU-IUCAKERBSA-N 0.000 claims 1
- HASRFYOMVPJRPU-SRVKXCTJSA-N Leu-Arg-Glu Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(O)=O)C(O)=O HASRFYOMVPJRPU-SRVKXCTJSA-N 0.000 claims 1
- RVVBWTWPNFDYBE-SRVKXCTJSA-N Leu-Glu-Arg Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O RVVBWTWPNFDYBE-SRVKXCTJSA-N 0.000 claims 1
- NPBGTPKLVJEOBE-IUCAKERBSA-N Lys-Arg Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=N NPBGTPKLVJEOBE-IUCAKERBSA-N 0.000 claims 1
- JGAMUXDWYSXYLM-SRVKXCTJSA-N Lys-Arg-Glu Chemical compound [H]N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O JGAMUXDWYSXYLM-SRVKXCTJSA-N 0.000 claims 1
- DRCILAJNUJKAHC-SRVKXCTJSA-N Lys-Glu-Arg Chemical compound [H]N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O DRCILAJNUJKAHC-SRVKXCTJSA-N 0.000 claims 1
- UASDAHIAHBRZQV-YUMQZZPRSA-N Met-Arg Chemical compound CSCC[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=N UASDAHIAHBRZQV-YUMQZZPRSA-N 0.000 claims 1
- KQBJYJXPZBNEIK-DCAQKATOSA-N Met-Glu-Arg Chemical compound CSCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@H](C(O)=O)CCCNC(N)=N KQBJYJXPZBNEIK-DCAQKATOSA-N 0.000 claims 1
- 208000003926 Myelitis Diseases 0.000 claims 1
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- 208000018737 Parkinson disease Diseases 0.000 claims 1
- OZILORBBPKKGRI-RYUDHWBXSA-N Phe-Arg Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 OZILORBBPKKGRI-RYUDHWBXSA-N 0.000 claims 1
- MPGJIHFJCXTVEX-KKUMJFAQSA-N Phe-Arg-Glu Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O MPGJIHFJCXTVEX-KKUMJFAQSA-N 0.000 claims 1
- HOYQLNNGMHXZDW-KKUMJFAQSA-N Phe-Glu-Arg Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O HOYQLNNGMHXZDW-KKUMJFAQSA-N 0.000 claims 1
- 208000010366 Postpoliomyelitis syndrome Diseases 0.000 claims 1
- IHCXPSYCHXFXKT-DCAQKATOSA-N Pro-Arg-Glu Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O IHCXPSYCHXFXKT-DCAQKATOSA-N 0.000 claims 1
- PULPZRAHVFBVTO-DCAQKATOSA-N Pro-Glu-Arg Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O PULPZRAHVFBVTO-DCAQKATOSA-N 0.000 claims 1
- 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010038910 Retinitis Diseases 0.000 claims 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- RZEQTVHJZCIUBT-WDSKDSINSA-N Ser-Arg Chemical compound OC[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=N RZEQTVHJZCIUBT-WDSKDSINSA-N 0.000 claims 1
- YUSRGTQIPCJNHQ-CIUDSAMLSA-N Ser-Arg-Glu Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O YUSRGTQIPCJNHQ-CIUDSAMLSA-N 0.000 claims 1
- PVDTYLHUWAEYGY-CIUDSAMLSA-N Ser-Glu-Arg Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O PVDTYLHUWAEYGY-CIUDSAMLSA-N 0.000 claims 1
- UKBSDLHIKIXJKH-HJGDQZAQSA-N Thr-Arg-Glu Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O UKBSDLHIKIXJKH-HJGDQZAQSA-N 0.000 claims 1
- FHDLKMFZKRUQCE-HJGDQZAQSA-N Thr-Glu-Arg Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O FHDLKMFZKRUQCE-HJGDQZAQSA-N 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- LCPVBXOHXMBLFW-JSGCOSHPSA-N Trp-Arg Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)=CNC2=C1 LCPVBXOHXMBLFW-JSGCOSHPSA-N 0.000 claims 1
- HYNAKPYFEYJMAS-XIRDDKMYSA-N Trp-Arg-Glu Chemical compound [H]N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O HYNAKPYFEYJMAS-XIRDDKMYSA-N 0.000 claims 1
- PKUJMYZNJMRHEZ-XIRDDKMYSA-N Trp-Glu-Arg Chemical compound [H]N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O PKUJMYZNJMRHEZ-XIRDDKMYSA-N 0.000 claims 1
- HTHCZRWCFXMENJ-KKUMJFAQSA-N Tyr-Arg-Glu Chemical compound [H]N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O HTHCZRWCFXMENJ-KKUMJFAQSA-N 0.000 claims 1
- XQYHLZNPOTXRMQ-KKUMJFAQSA-N Tyr-Glu-Arg Chemical compound [H]N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O XQYHLZNPOTXRMQ-KKUMJFAQSA-N 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- IBIDRSSEHFLGSD-YUMQZZPRSA-N Val-Arg Chemical compound CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N IBIDRSSEHFLGSD-YUMQZZPRSA-N 0.000 claims 1
- KKHRWGYHBZORMQ-NHCYSSNCSA-N Val-Arg-Glu Chemical compound CC(C)[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N KKHRWGYHBZORMQ-NHCYSSNCSA-N 0.000 claims 1
- BRPKEERLGYNCNC-NHCYSSNCSA-N Val-Glu-Arg Chemical compound CC(C)[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@H](C(O)=O)CCCN=C(N)N BRPKEERLGYNCNC-NHCYSSNCSA-N 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 108010001271 arginyl-glutamyl-arginine Proteins 0.000 claims 1
- 108010052670 arginyl-glutamyl-glutamic acid Proteins 0.000 claims 1
- 108010068380 arginylarginine Proteins 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000009977 dual effect Effects 0.000 claims 1
- 208000019258 ear infection Diseases 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- -1 et-Arg-Glu Chemical compound 0.000 claims 1
- 239000003889 eye drop Substances 0.000 claims 1
- 229940012356 eye drops Drugs 0.000 claims 1
- 108010085059 glutamyl-arginyl-proline Proteins 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 238000001802 infusion Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 238000010255 intramuscular injection Methods 0.000 claims 1
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 238000007913 intrathecal administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 108010000761 leucylarginine Proteins 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 108010018625 phenylalanylarginine Proteins 0.000 claims 1
- 230000006785 proliferative vitreoretinopathy Effects 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 125000006850 spacer group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 206010043778 thyroiditis Diseases 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- IBIDRSSEHFLGSD-UHFFFAOYSA-N valinyl-arginine Natural products CC(C)C(N)C(=O)NC(C(O)=O)CCCN=C(N)N IBIDRSSEHFLGSD-UHFFFAOYSA-N 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 abstract 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 abstract 1
- 102000016359 Fibronectins Human genes 0.000 abstract 1
- 108010067306 Fibronectins Proteins 0.000 abstract 1
- 230000024932 T cell mediated immunity Effects 0.000 abstract 1
- 210000002744 extracellular matrix Anatomy 0.000 abstract 1
- 230000003902 lesion Effects 0.000 abstract 1
Abstract
L'invention concerne des peptides représentés par les formules ci-après: (i) Xaa - Yaa - Arg, dans laquelle Xaa est un résidu d'acide aminé et Yaa est Glu ou Xaa est absent et Yaa est un résidu d'acide aminé à l'exception de Pro; (ii) Arg - Yaa - Xaa, dans laquelle Xaa est un résidu d'acide aminé et Yaa est Glu ou Xaa est absent et Yaa est un résidu d'acide aminé à l'exception d'Asn; (iii) Xaa - Arg - Yaa, dans laquelle Xaa est un résidu d'acide aminé et Yaa est Glu; et (iv) Yaa - Arg - Xaa, dans laquelle Xaa est un résidu d'acide aminé et Yaa est Glu. L'invention concerne également des dérivés desdits peptides, ces peptides et dérivés exerçant un effet inhibiteur sur la migration des macrophages et/ou sur l'activité phagocytique des macrophages. En outre, les peptides et dérivés exercent un effet inhibiteur sur la capacité des macrophages et des cellules T à adhérer à la matrice extracellulaire et/ou la fibronectine. Les peptides et dérivés ont un effet inhibiteur sur la réaction immunitaire humorale et/ou cellulaire. L'invention concerne également des procédés d'utilisation desdits peptides et dérivés et des compositions les contenant, utilisés pour inhiber des inflammations, dont l'inflammation d'une articulation, du système nerveux central, de points de lésions spécifiques du système nerveux central ou d'autres sites immunitaires privilégiés.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97937794A EP0927191A2 (fr) | 1996-09-03 | 1997-09-03 | Peptides anti-inflammatoires et leurs utilisations |
| CA002264285A CA2264285A1 (fr) | 1996-09-03 | 1997-09-03 | Peptides anti-inflammatoires et leurs utilisations |
| AU40301/97A AU4030197A (en) | 1996-09-03 | 1997-09-03 | Anti-inflammatory peptides and uses thereof |
| JP10512435A JP2001500492A (ja) | 1996-09-03 | 1997-09-03 | 抗炎症性ペプチドおよびその使用 |
| IL12852997A IL128529A0 (en) | 1996-09-03 | 1997-09-03 | Anti-inflammatory peptides and uses thereof |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2537696P | 1996-09-03 | 1996-09-03 | |
| US75314196A | 1996-11-20 | 1996-11-20 | |
| US08/864,301 | 1997-05-28 | ||
| US60/025,376 | 1997-05-28 | ||
| US08/864,301 US6126939A (en) | 1996-09-03 | 1997-05-28 | Anti-inflammatory dipeptide and pharmaceutical composition thereof |
| US08/753,141 | 1997-05-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1998009985A2 WO1998009985A2 (fr) | 1998-03-12 |
| WO1998009985A3 WO1998009985A3 (fr) | 1998-05-07 |
| WO1998009985B1 true WO1998009985B1 (fr) | 1998-06-18 |
Family
ID=27362525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IL1997/000295 WO1998009985A2 (fr) | 1996-09-03 | 1997-09-03 | Peptides anti-inflammatoires et leurs utilisations |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6126939A (fr) |
| EP (1) | EP0927191A2 (fr) |
| JP (1) | JP2001500492A (fr) |
| AU (1) | AU4030197A (fr) |
| CA (1) | CA2264285A1 (fr) |
| IL (1) | IL128529A0 (fr) |
| WO (1) | WO1998009985A2 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7442778B2 (en) | 2004-09-24 | 2008-10-28 | Amgen Inc. | Modified Fc molecules |
Families Citing this family (148)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7074888B1 (en) * | 1995-03-17 | 2006-07-11 | The Research Foundation Of State University Of New York | Mimotopes and anti-mimotopes of human platelet glycoprotein Ib/IX |
| FR2767135B1 (fr) * | 1997-08-06 | 2002-07-12 | Genset Sa | Recepteur complexe lsr, activite, clonage, et application au diagnostic, a la prevention et/ou au traitement de d'obesite et des risques ou complications associes |
| SE9703531D0 (sv) * | 1997-09-30 | 1997-09-30 | Rudolf Valenta | Non-anaphlactic forms of allergens and their use |
| CA2225325A1 (fr) * | 1997-12-19 | 1999-06-19 | The University Of British Columbia | Substances hemiasterlines analogues |
| NZ506839A (en) * | 1998-03-09 | 2003-05-30 | Zealand Pharma As | Pharmacologically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
| US6660843B1 (en) | 1998-10-23 | 2003-12-09 | Amgen Inc. | Modified peptides as therapeutic agents |
| US7488590B2 (en) | 1998-10-23 | 2009-02-10 | Amgen Inc. | Modified peptides as therapeutic agents |
| DE69934425T2 (de) | 1998-10-23 | 2007-09-27 | Amgen Inc., Thousand Oaks | Thrombopoietin substitute |
| AR023819A1 (es) * | 1999-05-03 | 2002-09-04 | Astrazeneca Ab | FORMULACIoN FARMACEUTICA, KIT DE PARTES Y UTILIZACION DE DICHA FORMULACION |
| WO2000077166A2 (fr) * | 1999-06-10 | 2000-12-21 | Digital Gene Technologies, Inc. | Expression genique modulee dans des inflammations gastro-intestinales |
| CA2378480A1 (fr) * | 1999-08-09 | 2001-02-15 | Tripep Ab | Inhibiteurs de polymerisation de proteines et leur procede d'utilisation |
| US6258932B1 (en) | 1999-08-09 | 2001-07-10 | Tripep Ab | Peptides that block viral infectivity and methods of use thereof |
| AU783925B2 (en) * | 1999-08-10 | 2005-12-22 | Uab Research Foundation | Method of treating traumatic brain and spinal cord injuries and other neurogenic conditions using non-steroidal anti-inflammatory drugs and naturally occurring conotoxins |
| US7855181B2 (en) * | 1999-08-13 | 2010-12-21 | University Of Florida Research Foundation, Inc. | Dipeptides for prevention of muscle breakdown and microbial infection |
| US6989367B2 (en) * | 2000-01-14 | 2006-01-24 | Genset S.A. | OBG3 globular head and uses thereof |
| US7338787B2 (en) * | 2000-01-14 | 2008-03-04 | Serono Genetics Institute S.A. | Nucleic acids encoding OBG3 globular head and uses thereof |
| US20020058617A1 (en) * | 2000-01-14 | 2002-05-16 | Joachim Fruebis | OBG3 globular head and uses thereof for decreasing body mass |
| GB0009760D0 (en) | 2000-04-19 | 2000-06-07 | Oxford Biomedica Ltd | Method |
| EP1294740A2 (fr) * | 2000-06-16 | 2003-03-26 | Hercules Incorporated | Peptides modifies chimiquement, compositions et leur procede de production et d'utilisation |
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| US4244946A (en) * | 1979-06-11 | 1981-01-13 | The Salk Institute For Biological Studies | Water-soluble peptides affecting gonadal function |
| US4305872A (en) * | 1979-10-19 | 1981-12-15 | Kenneth Wingrove | Polypeptide derivatives |
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| EP0215805A1 (fr) * | 1985-01-18 | 1987-04-01 | MERCK PATENT GmbH | Peptides de regulation immunitaire |
| US5510329A (en) * | 1988-04-26 | 1996-04-23 | Ramot University For Applied Research And Industrial Development Ltd. | Preparations for the treatment of eyes |
| US5506231A (en) * | 1989-03-31 | 1996-04-09 | The Children's Medical Center Corporation | Treatment of aids dementia, myelopathy and blindness |
| US5455279A (en) * | 1991-04-19 | 1995-10-03 | The Children's Medical Center Corporation | Regimen method of mediating neuronal damage using nitroglycerine |
| IT1264129B1 (it) * | 1993-04-09 | 1996-09-16 | Codev S A | Peptidi ad attivita' immunomodulatoria derivati da frammenti di leucochinina |
| AU7392294A (en) * | 1993-07-21 | 1995-02-20 | Vladimir Khatskelevich Khavinson | Pharmaceutical with immunomodulating activity |
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1997
- 1997-05-28 US US08/864,301 patent/US6126939A/en not_active Expired - Fee Related
- 1997-09-03 WO PCT/IL1997/000295 patent/WO1998009985A2/fr not_active Application Discontinuation
- 1997-09-03 EP EP97937794A patent/EP0927191A2/fr not_active Withdrawn
- 1997-09-03 AU AU40301/97A patent/AU4030197A/en not_active Abandoned
- 1997-09-03 CA CA002264285A patent/CA2264285A1/fr not_active Abandoned
- 1997-09-03 IL IL12852997A patent/IL128529A0/xx unknown
- 1997-09-03 JP JP10512435A patent/JP2001500492A/ja active Pending
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| US7442778B2 (en) | 2004-09-24 | 2008-10-28 | Amgen Inc. | Modified Fc molecules |
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| DE69606552T2 (de) | Acylierte enolderivate von alpha-ketoestern und alpha-ketoamiden |