WO1997031019B1 - Peptides antipathogenes et compositions les contenant - Google Patents
Peptides antipathogenes et compositions les contenantInfo
- Publication number
- WO1997031019B1 WO1997031019B1 PCT/IL1997/000066 IL9700066W WO9731019B1 WO 1997031019 B1 WO1997031019 B1 WO 1997031019B1 IL 9700066 W IL9700066 W IL 9700066W WO 9731019 B1 WO9731019 B1 WO 9731019B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- leu
- lys
- amino acid
- ile
- ser
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract 16
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract 16
- 239000000203 mixture Substances 0.000 title claims 5
- 230000001775 anti-pathogenic Effects 0.000 title 1
- 230000001461 cytolytic Effects 0.000 claims abstract 25
- 150000001413 amino acids Chemical class 0.000 claims abstract 15
- 230000002949 hemolytic Effects 0.000 claims abstract 14
- 150000008574 D-amino acids Chemical group 0.000 claims abstract 10
- 230000001717 pathogenic Effects 0.000 claims abstract 10
- 150000008575 L-amino acids Chemical group 0.000 claims abstract 6
- 230000002209 hydrophobic Effects 0.000 claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
- CTVQQQPWNOVEAG-QDOPKCMFSA-N Pardaxin Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(O)=O)[C@@H](C)CC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)CN)C1=CC=CC=C1 CTVQQQPWNOVEAG-QDOPKCMFSA-N 0.000 claims abstract 4
- 125000000539 amino acid group Chemical group 0.000 claims abstract 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract 4
- 108010036176 Melitten Proteins 0.000 claims abstract 3
- 201000011510 cancer Diseases 0.000 claims abstract 2
- 230000000875 corresponding Effects 0.000 claims abstract 2
- 235000001014 amino acid Nutrition 0.000 claims 11
- 210000004027 cells Anatomy 0.000 claims 9
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 5
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 4
- 239000004472 Lysine Substances 0.000 claims 4
- 229960003136 leucine Drugs 0.000 claims 4
- 241000894006 Bacteria Species 0.000 claims 3
- 206010057248 Cell death Diseases 0.000 claims 3
- 210000003743 Erythrocytes Anatomy 0.000 claims 3
- 210000003324 RBC Anatomy 0.000 claims 3
- 230000009089 cytolysis Effects 0.000 claims 3
- 229920005604 random copolymer Polymers 0.000 claims 3
- 229960003767 Alanine Drugs 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000003636 chemical group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- VDXZNPDIRNWWCW-JFTDCZMZSA-N melittin Chemical compound NCC(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(N)=O)CC1=CNC2=CC=CC=C12 VDXZNPDIRNWWCW-JFTDCZMZSA-N 0.000 claims 2
- 229960004295 valine Drugs 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 1
- 229960001230 Asparagine Drugs 0.000 claims 1
- 210000000170 Cell Membrane Anatomy 0.000 claims 1
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 claims 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 claims 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 claims 1
- 229960002449 Glycine Drugs 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 229960000310 ISOLEUCINE Drugs 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-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
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001176 L-lysyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 241000204031 Mycoplasma Species 0.000 claims 1
- 229960005190 Phenylalanine Drugs 0.000 claims 1
- 229960002429 Proline Drugs 0.000 claims 1
- 239000004473 Threonine Substances 0.000 claims 1
- 229960004799 Tryptophan Drugs 0.000 claims 1
- 229960004441 Tyrosine Drugs 0.000 claims 1
- -1 aminoethylamino groups Chemical group 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 230000005591 charge neutralization Effects 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- 230000003247 decreasing Effects 0.000 claims 1
- 201000009910 diseases by infectious agent Diseases 0.000 claims 1
- 235000004554 glutamine Nutrition 0.000 claims 1
- 230000003211 malignant Effects 0.000 claims 1
- 235000006109 methionine Nutrition 0.000 claims 1
- 230000001264 neutralization Effects 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 235000004400 serine Nutrition 0.000 claims 1
- 235000008521 threonine Nutrition 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 abstract 1
- VDXZNPDIRNWWCW-UHFFFAOYSA-N Melitten Chemical compound NCC(=O)NC(C(C)CC)C(=O)NCC(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)O)C(=O)NC(C(C)O)C(=O)NCC(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(C(C)CC)C(=O)NC(CO)C(=O)NC(C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCCN)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCC(N)=O)C(=O)NC(CCC(N)=O)C(N)=O)CC1=CNC2=CC=CC=C12 VDXZNPDIRNWWCW-UHFFFAOYSA-N 0.000 abstract 1
- 206010028470 Mycoplasma infection Diseases 0.000 abstract 1
- 208000010362 Protozoan Infections Diseases 0.000 abstract 1
- 206010047461 Viral infection Diseases 0.000 abstract 1
- 208000001756 Virus Disease Diseases 0.000 abstract 1
- 230000000844 anti-bacterial Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 244000052769 pathogens Species 0.000 abstract 1
Abstract
On a découvert que les peptides ayant une charge positive nette et ne présentant pas de configuration en hélice α ou une configuration en hélice α seulement partielle, ont une activité cytolytique sélective non hémolytique. Les peptides peuvent être dérivés de peptides naturels tels que la pardaxine et la mellitine et des fragments de celles-ci, dans lesquels les restes de L-aminoacides sont remplacés par des restes de D-aminoacides correspondants, et des dérivés cycliques de ces derniers, ou sont des diastéréoisomères de peptides linéaires à teneurs variables en au moins un acide aminé à charge positive et en au moins un acide aminé hydrophobe, et dans lesquels au moins un des restes d'aminoacides est un D-aminoacide, et de préférence au moins un tiers de la séquence se compose de restes de D-aminoacides. Des compositions pharmaceutiques comprenant les peptides cytolytiques non hémolytiques peuvent être utilisés pour le traitement de plusieurs maladies induites par des pathogènes dont les infections bactériennes, fongiques, virales, à mycoplasma et dues à des protozaires et pour le traitement du cancer.
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL12573497A IL125734A (en) | 1996-02-22 | 1997-02-20 | Antipathogenic peptides and compositions comprising them |
| JP9529954A JP2000506128A (ja) | 1996-02-22 | 1997-02-20 | 抗病原性ペプチドおよびこれらを含む組成物 |
| EA199800754A EA199800754A1 (ru) | 1996-02-22 | 1997-02-20 | Противопатогенные пептиды и композиции, их включающие |
| AU17319/97A AU730069B2 (en) | 1996-02-22 | 1997-02-20 | Antipathogenic peptides and compositions comprising them |
| EP97904561A EP0904291A2 (fr) | 1996-02-22 | 1997-02-20 | Peptides antipathogenes et compositions les contenant |
| NZ331219A NZ331219A (en) | 1996-02-22 | 1997-02-20 | Antipathogenic peptides having a non-hemolytic selective cytolytic activity and compositions comprising them |
| BR9707691A BR9707691A (pt) | 1996-02-22 | 1997-02-20 | Peptídios antipatogênicos e composições que compreendem os mesmos |
| US09/125,605 US6172038B1 (en) | 1996-02-22 | 1997-02-20 | Antipathogenic peptides and compositions comprising them |
| IL13136898A IL131368A0 (en) | 1997-02-20 | 1998-02-19 | Antipathogenic synthetic peptides and compositions comprising them |
| CA002281204A CA2281204A1 (fr) | 1997-02-20 | 1998-02-19 | Peptides synthetiques antipathogenes et compositions les contenant |
| JP53645398A JP2001512475A (ja) | 1997-02-20 | 1998-02-19 | 抗病原性合成ペプチドおよびこれらを含む組成物 |
| KR1019997007477A KR20000071187A (ko) | 1996-02-22 | 1998-02-19 | 항병원성 합성 펩타이드와 그 구성물 |
| CN98804347A CN1252808A (zh) | 1997-02-20 | 1998-02-19 | 抗病原合成肽及包含该肽类的组合物 |
| PCT/IL1998/000081 WO1998037090A1 (fr) | 1997-02-20 | 1998-02-19 | Peptides synthetiques antipathogenes et compositions les contenant |
| US09/367,714 US7001983B1 (en) | 1997-02-20 | 1998-02-19 | Antipathogenic synthetic peptides and compositions comprising them |
| AU60056/98A AU6005698A (en) | 1997-02-20 | 1998-02-19 | Antipathogenic synthetic peptides and compositions comprising them |
| EP98903286A EP0977774A1 (fr) | 1997-02-20 | 1998-02-19 | Peptides synthetiques antipathogenes et compositions les contenant |
| BR9807456-3A BR9807456A (pt) | 1997-02-20 | 1998-02-19 | Peptìdios antipatogênicos sintéticos e composições que compreendem os mesmos |
| EA199900752A EA199900752A1 (ru) | 1997-02-20 | 1998-02-19 | Противопатогенные синтетические пептиды и композиции, их включающие |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL11722396A IL117223A0 (en) | 1996-02-22 | 1996-02-22 | Antipathogenic polypeptides and compositions comprising them |
| IL117223 | 1996-02-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1997031019A2 WO1997031019A2 (fr) | 1997-08-28 |
| WO1997031019A3 WO1997031019A3 (fr) | 1997-10-23 |
| WO1997031019B1 true WO1997031019B1 (fr) | 1997-10-23 |
Family
ID=11068576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IL1997/000066 WO1997031019A2 (fr) | 1996-02-22 | 1997-02-20 | Peptides antipathogenes et compositions les contenant |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6172038B1 (fr) |
| EP (1) | EP0904291A2 (fr) |
| JP (1) | JP2000506128A (fr) |
| KR (2) | KR19990087100A (fr) |
| CN (1) | CN1216549A (fr) |
| AU (1) | AU730069B2 (fr) |
| BR (1) | BR9707691A (fr) |
| CA (1) | CA2247025A1 (fr) |
| CZ (1) | CZ264398A3 (fr) |
| EA (1) | EA199800754A1 (fr) |
| IL (2) | IL117223A0 (fr) |
| NZ (1) | NZ331219A (fr) |
| WO (1) | WO1997031019A2 (fr) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA199900752A1 (ru) * | 1997-02-20 | 2000-06-26 | Йеда Рисерч Энд Дивелопмент Ко. Лтд. | Противопатогенные синтетические пептиды и композиции, их включающие |
| AU750414B2 (en) | 1998-07-13 | 2002-07-18 | Board Of Regents, The University Of Texas System | Cancer treatment methods using therapeutic conjugates that bind to aminophospholipids |
| US6818213B1 (en) | 1998-07-13 | 2004-11-16 | Board Of Regents, The University Of Texas System | Cancer treatment compositions comprising therapeutic conjugates that bind to aminophospholipids |
| HU228582B1 (en) | 1998-10-23 | 2013-04-29 | Kirin Amgen Inc | Dimeric thrombopoietin peptide mimetics binding to mp1 receptor and having thrombopoietic activity |
| US7488590B2 (en) | 1998-10-23 | 2009-02-10 | Amgen Inc. | Modified peptides as therapeutic agents |
| US6660843B1 (en) | 1998-10-23 | 2003-12-09 | Amgen Inc. | Modified peptides as therapeutic agents |
| GB0005703D0 (en) | 2000-03-09 | 2000-05-03 | Alpharma As | Compounds |
| IL139720A0 (en) * | 2000-11-16 | 2002-02-10 | Yeda Res & Dev | Diastereomeric peptides and pharmaceutical compositions comprising them |
| US7671011B2 (en) * | 2003-06-19 | 2010-03-02 | Yeda Research & Development Co. Ltd. | Antimicrobial and anticancer lipopeptides |
| US8143380B2 (en) | 2004-07-08 | 2012-03-27 | Amgen Inc. | Therapeutic peptides |
| EP1814575A4 (fr) * | 2004-11-24 | 2010-07-07 | Neopro Labs Llc | Methodes et compositions pour traiter des troubles |
| WO2006128289A1 (fr) * | 2005-06-02 | 2006-12-07 | University Of Manitoba | Utilisation de brevinin-2r dans le traitement du cancer |
| US8008453B2 (en) | 2005-08-12 | 2011-08-30 | Amgen Inc. | Modified Fc molecules |
| EP1973556A2 (fr) * | 2005-12-27 | 2008-10-01 | Yeda Research And Development Co., Ltd. | Peptides diastereomeres contenant de l'histidine et leurs utilisations |
| CA2637221A1 (fr) | 2006-02-10 | 2007-08-16 | Dermagen Ab | Nouveaux peptides antimicrobiens et leur utilisation |
| US9283260B2 (en) | 2006-04-21 | 2016-03-15 | Amgen Inc. | Lyophilized therapeutic peptibody formulations |
| WO2014038004A1 (fr) * | 2012-09-05 | 2014-03-13 | 株式会社メニコン | Lentille ophtalmique à libération de médicament lente et son procédé de fabrication |
| JP6093528B2 (ja) * | 2012-09-19 | 2017-03-08 | 株式会社ミルボン | スクリーニング方法 |
| WO2017134661A1 (fr) | 2016-02-04 | 2017-08-10 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Procédés de destruction de biofilms |
| GB2557654A (en) * | 2016-12-14 | 2018-06-27 | Uea Enterprises Ltd | Method for nucleic acid depletion |
| CN113528600A (zh) * | 2021-07-08 | 2021-10-22 | 石河子大学 | 一种利用沙门氏菌诱导蝇蛆制备抗菌肽的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258454A (en) * | 1988-09-01 | 1993-11-02 | Riso National Laboratory | Peptide synthesis method and solid support for use in the method |
-
1996
- 1996-02-22 IL IL11722396A patent/IL117223A0/xx unknown
-
1997
- 1997-02-20 KR KR1019980706488A patent/KR19990087100A/ko not_active Application Discontinuation
- 1997-02-20 AU AU17319/97A patent/AU730069B2/en not_active Ceased
- 1997-02-20 NZ NZ331219A patent/NZ331219A/xx unknown
- 1997-02-20 CN CN97194000A patent/CN1216549A/zh active Pending
- 1997-02-20 US US09/125,605 patent/US6172038B1/en not_active Expired - Fee Related
- 1997-02-20 IL IL12573497A patent/IL125734A/xx not_active IP Right Cessation
- 1997-02-20 WO PCT/IL1997/000066 patent/WO1997031019A2/fr not_active Application Discontinuation
- 1997-02-20 BR BR9707691A patent/BR9707691A/pt unknown
- 1997-02-20 CZ CZ982643A patent/CZ264398A3/cs unknown
- 1997-02-20 EP EP97904561A patent/EP0904291A2/fr not_active Ceased
- 1997-02-20 EA EA199800754A patent/EA199800754A1/ru unknown
- 1997-02-20 JP JP9529954A patent/JP2000506128A/ja not_active Ceased
- 1997-02-20 CA CA002247025A patent/CA2247025A1/fr not_active Abandoned
-
1998
- 1998-02-19 KR KR1019997007477A patent/KR20000071187A/ko not_active Application Discontinuation
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