CA2446848C - Derivatives of magainin - Google Patents
Derivatives of magainin Download PDFInfo
- Publication number
- CA2446848C CA2446848C CA2446848A CA2446848A CA2446848C CA 2446848 C CA2446848 C CA 2446848C CA 2446848 A CA2446848 A CA 2446848A CA 2446848 A CA2446848 A CA 2446848A CA 2446848 C CA2446848 C CA 2446848C
- Authority
- CA
- Canada
- Prior art keywords
- seq
- peptide
- magainin
- lys
- magainin derivative
- Prior art date
- 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.)
- Expired - Lifetime
Links
- 108060003100 Magainin Proteins 0.000 title claims abstract description 78
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- 238000000034 method Methods 0.000 claims abstract description 16
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- 238000010532 solid phase synthesis reaction Methods 0.000 claims abstract description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 49
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 239000012634 fragment Substances 0.000 claims description 15
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- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 4
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- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000003275 alpha amino acid group Chemical group 0.000 claims 6
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 2
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- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 6
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 5
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 241000699670 Mus sp. Species 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
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- MGIUUAHJVPPFEV-ABXDCCGRSA-N magainin ii Chemical compound C([C@H](NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(O)=O)C1=CC=CC=C1 MGIUUAHJVPPFEV-ABXDCCGRSA-N 0.000 description 3
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN01112855.0 | 2001-05-10 | ||
| CNB011128550A CN1158304C (zh) | 2001-05-10 | 2001-05-10 | 蛙皮抗菌肽衍生物 |
| PCT/CN2002/000317 WO2003016339A1 (fr) | 2001-05-10 | 2002-05-08 | Derive peptidique antibacterien de peau de grenouille |
Publications (2)
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| CA2446848A1 CA2446848A1 (en) | 2003-02-27 |
| CA2446848C true CA2446848C (en) | 2013-09-10 |
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| CA2446848A Expired - Lifetime CA2446848C (en) | 2001-05-10 | 2002-05-08 | Derivatives of magainin |
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|---|---|
| US (2) | US7232800B2 (enExample) |
| EP (1) | EP1386928B1 (enExample) |
| JP (1) | JP4194941B2 (enExample) |
| KR (1) | KR100902209B1 (enExample) |
| CN (1) | CN1158304C (enExample) |
| AU (1) | AU2002257498B2 (enExample) |
| BR (1) | BRPI0209684B8 (enExample) |
| CA (1) | CA2446848C (enExample) |
| WO (1) | WO2003016339A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1158304C (zh) * | 2001-05-10 | 2004-07-21 | 上海华谊生物技术有限公司 | 蛙皮抗菌肽衍生物 |
| US7550426B2 (en) * | 2005-05-18 | 2009-06-23 | Ghc Research Development Corporation | Acetylated therapeutic procytotoxins |
| CN100575359C (zh) * | 2006-04-17 | 2009-12-30 | 中国科学院成都生物研究所 | 一种无指盘臭蛙抗菌肽及其用途 |
| CN100522993C (zh) * | 2006-05-30 | 2009-08-05 | 中国科学院昆明动物研究所 | 无指盘臭蛙抗菌肽 |
| CN101182360B (zh) * | 2007-10-08 | 2010-07-07 | 国家海洋局第一海洋研究所 | 一种具有抗菌功能的融合蛋白及其应用 |
| CN101928340A (zh) * | 2009-12-24 | 2010-12-29 | 深圳市圣西马生物技术有限公司 | 一组抗菌肽衍生物及其应用 |
| CN102796177A (zh) * | 2012-08-13 | 2012-11-28 | 中国科学院烟台海岸带研究所 | 一种改造体抗菌肽及其制备方法和应用 |
| CN102786583B (zh) * | 2012-08-13 | 2014-03-19 | 中国科学院烟台海岸带研究所 | 一种昆嵛林蛙改造体抗菌肽及其制备方法和应用 |
| GB201409451D0 (en) | 2014-05-28 | 2014-07-09 | Ipabc Ltd | Antimicrobial preparations, methods for preparing the same and uses thereof to combat microorganisms |
| JP7105696B2 (ja) | 2016-02-29 | 2022-07-25 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | 感染症を治療するステープル化細胞内ターゲティング抗微生物ペプチド |
| WO2018100408A1 (en) * | 2016-11-30 | 2018-06-07 | Sasinapas Co.,Ltd. | Modified peptides |
| CN106749594B (zh) * | 2016-12-27 | 2020-02-14 | 王天放 | 包含f1、f3多肽的药物组合物及其在治疗hpv感染疾病中的应用 |
| JP7305614B2 (ja) * | 2017-07-19 | 2023-07-10 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | 抗生物質耐性細菌感染症の処置のための安定化抗菌ペプチド |
| CN110042138B (zh) * | 2019-04-10 | 2020-12-29 | 常熟理工学院 | 一种林蛙油抗氧化肽组分的制备方法及其分离方法与用途 |
| JP7717797B2 (ja) * | 2021-09-03 | 2025-08-04 | 深▲セン▼千越生物科技有限公司 | 抗菌ペプチド又はペプチド誘導体、置換体及びその組成物、製造方法及び応用 |
| CN117643563B (zh) * | 2024-01-29 | 2024-03-29 | 广州首漾医药生物科技有限公司 | 一种抑菌除螨膏霜及制备方法 |
| CN118064343B (zh) * | 2024-03-11 | 2025-01-03 | 华南农业大学 | 一种产四种抗菌肽的重组枯草芽孢杆菌、构建方法及其应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912231A (en) * | 1989-07-07 | 1999-06-15 | Scripps Clinic And Research Foundation | Substitution analogues of magainin peptides |
| US5792831A (en) * | 1990-02-08 | 1998-08-11 | Magainin Pharmaceuticals Inc. | Analogues of magainin peptides containing D-amino acids |
| US5654274A (en) * | 1992-06-01 | 1997-08-05 | Magainin Pharmaceuticals, Inc. | Biologically active peptides having N-terminal substitutions |
| US5589364A (en) * | 1994-07-29 | 1996-12-31 | Magainin Pharmaceuticals Inc. | Recombinant production of biologically active peptides and proteins |
| US6461834B1 (en) * | 1998-11-06 | 2002-10-08 | Bionebraska, Inc. | Clostripain catalyzed amidation of peptides |
| EP1076066A1 (en) * | 1999-07-12 | 2001-02-14 | Zealand Pharmaceuticals A/S | Peptides for lowering blood glucose levels |
| CN1158304C (zh) * | 2001-05-10 | 2004-07-21 | 上海华谊生物技术有限公司 | 蛙皮抗菌肽衍生物 |
-
2001
- 2001-05-10 CN CNB011128550A patent/CN1158304C/zh not_active Expired - Lifetime
-
2002
- 2002-05-08 WO PCT/CN2002/000317 patent/WO2003016339A1/zh not_active Ceased
- 2002-05-08 AU AU2002257498A patent/AU2002257498B2/en not_active Expired
- 2002-05-08 BR BRPI0209684A patent/BRPI0209684B8/pt not_active IP Right Cessation
- 2002-05-08 CA CA2446848A patent/CA2446848C/en not_active Expired - Lifetime
- 2002-05-08 JP JP2003521261A patent/JP4194941B2/ja not_active Expired - Lifetime
- 2002-05-08 KR KR1020037014458A patent/KR100902209B1/ko not_active Expired - Lifetime
- 2002-05-08 EP EP02727168.3A patent/EP1386928B1/en not_active Expired - Lifetime
-
2003
- 2003-11-10 US US10/705,106 patent/US7232800B2/en not_active Expired - Lifetime
-
2007
- 2007-03-14 US US11/686,190 patent/US20070166790A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1386928B1 (en) | 2015-10-14 |
| JP4194941B2 (ja) | 2008-12-10 |
| US20070166790A1 (en) | 2007-07-19 |
| KR100902209B1 (ko) | 2009-06-11 |
| BR0209684A (pt) | 2004-07-13 |
| BRPI0209684B1 (pt) | 2016-08-30 |
| CN1158304C (zh) | 2004-07-21 |
| KR20030094388A (ko) | 2003-12-11 |
| EP1386928A4 (en) | 2005-04-13 |
| US20040197864A1 (en) | 2004-10-07 |
| BRPI0209684B8 (pt) | 2021-05-25 |
| JP2005502663A (ja) | 2005-01-27 |
| CA2446848A1 (en) | 2003-02-27 |
| WO2003016339A1 (fr) | 2003-02-27 |
| US7232800B2 (en) | 2007-06-19 |
| CN1363558A (zh) | 2002-08-14 |
| EP1386928A1 (en) | 2004-02-04 |
| AU2002257498B2 (en) | 2007-10-25 |
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