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Long lasting fusion peptide inhibitors of viral infection

An anti-virus, measles virus technology, applied in the direction of viral peptides, anti-viral agents, viruses, etc., can solve problems such as reducing effective anti-viral activity

Inactive Publication Date: 2005-11-23
CONJUCHEM BIOTECH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

thus greatly reducing the potent antiviral activity of the peptide

Method used

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  • Long lasting fusion peptide inhibitors of viral infection
  • Long lasting fusion peptide inhibitors of viral infection
  • Long lasting fusion peptide inhibitors of viral infection

Examples

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preparation example Construction

[0179] A particularly preferred method of preparing the compounds of the invention involves solid phase peptide synthesis in which the alpha-N-terminus of the amino acid is protected with an acid- or base-sensitive group. Such protecting groups should be stable to the conditions of peptide bond formation while being readily removable without disrupting the extended peptide chain or racemizing any chiral centers contained therein. Suitable protecting groups are: 9-fluorenylmethoxycarbonyl (Fmoc), tert-butoxycarbonyl (Boc), benzyloxycarbonyl (Cbz), biphenylisopropoxycarbonyl, tert-amyloxycarbonyl, Isobornyloxycarbonyl, α,α-dimethyl-3,5-dimethoxybenzyloxycarbonyl, o-nitrophenylsulfinyl, 2-cyano-tert-butoxycarbonyl and the like. The 9-fluorenyl-methoxycarbonyl (Fmoc) protecting group is particularly suitable for the synthesis of the peptides of the invention. Other preferred side chain protecting groups are: for side chain amino groups such as lysine and arginine, 2,2,5,7,8-penta...

Embodiment 1

[0221] Preparation of Modified DP178--

[0222] YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWFK(MPA)-NH 2 Synthesis

[0223] In this example, DP178 (SEQ ID NO: 1) was synthesized and modified to contain a linker and a maleimide group according to the following synthetic route. As described in U.S. Patents 6,013,236 and 6,020,459, DP178 is a potent inhibitor of HIV-1 and is capable of inhibiting cell-induced syncytium formation between HIV-1-infected and uninfected cells and the destruction of uninfected cells by cell-free HIV-1 virus infection.

[0224] Solid phase peptide synthesis of modified peptides on a 100 μmole scale was performed using manual solid phase synthesis, Symphony Peptide Synthesizer and Fmoc protected Rink amide MBHA resin. Add the following protected amino acids to the resin in sequence: Fmoc-Lys(Aloc)-OH, Fmoc-Phe-OH, Fmoc-Trp(Boc)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Trp(Boc)-OH , Fmoc-Leu-OH, Fmoc-Ser(tBu)-OH, Fmoc-Ala-OH, Fmoc-Trp(Boc)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Asp(tB...

Embodiment 2

[0228] Preparation of Modified DP107--

[0229] NNLLRAIEAQQHLLQLTVWQIKQLQARILAVERYLKDQK(MPA)NH 2 Synthesis

[0230] In this example, DP107 (SEQ ID NO: 2) was synthesized and modified to contain a linker and a maleimide group according to the following synthetic route. DP107 exhibits potent antiviral activity against HIV-1 as described in US Patent Nos. 6,013,236 and 6,020,459.

[0231] Solid-phase peptide synthesis of modified peptides on a 100 μmole scale was performed using manual solid-phase synthesis, a co-peptide synthesizer, and Fmoc-protected Rink amide MBHA resin. Add the following protected amino acids to the resin in sequence: Fmoc-Lys(Aloc)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Asp(tBu)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Leu-OH , Fmoc-Tyr(tBu)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Glu(tBu)-OH, Fmoc-Val-OH, Fmoc-Ala-OH, Fmoc-Leu-OH, Fmoc-Ile- OH, Fmoc-Arg(Pbf)-OH, Fmoc-Ala-OH, Fmoc-Gln(Trt)-OH, Fmoc-Leu-OH, Fmoc-Gln(Trt)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Ile-OH, Fmoc-Gln(Trt)-OH, Fmoc-Trp(Boc)-OH, ...

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Abstract

Peptides exhibiting anti-viral and anti-fusogenic activity are modified to provide greater stability and improved half-life in vivo. The selected peptides include fusion inhibitors DP178 and DP107 and related peptides and analogs thereof. The modified peptides are capable of forming covalent bonds with one or more blood components, preferably a mobile blood component.

Description

[0001] This application is a divisional application of the international application PCT / US00 / 13651, which entered the Chinese national phase on November 16, 2001, with the application number 00807671.5 and the invention name "Long-acting Fusion Peptide Inhibitor of Viral Infection". field of invention [0002] The present invention relates to modified peptides which are inhibitors of viral activity and / or exhibit anti-fusion properties. In particular, the present invention relates to modified peptide inhibitors of human immunodeficiency virus (HIV), respiratory syncytial virus (RSV), human parainfluenza virus (HPV), measles virus (MeV) and simian immunodeficiency virus (SIV) , which has a long-acting effect in the treatment of various viral infections. The present invention also relates to conjugates of modified peptides and endogenous carriers, in particular conjugates of modified peptides and various mobile blood components, especially mobile endogenous proteins. Backgrou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06A61K38/00C07K7/08C07K14/00C07K14/16
CPCA61K38/00C12N2740/16122C07K14/005A61P1/04A61P7/00A61P9/04A61P9/08A61P9/10A61P15/18A61P17/00A61P17/02A61P17/06A61P19/02A61P19/10A61P27/02A61P27/06A61P29/00A61P31/04A61P31/14A61P35/00A61P35/02A61P35/04A61P37/06
Inventor 多米尼克·P·布里顿罗伯特·P·迪弗雷纳尼塞·布迪耶莱布马丁·罗比塔利彼得·G·米尔纳
Owner CONJUCHEM BIOTECH INC
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