WO2006108586A3 - Polymyxin b analogs for lps detoxification - Google Patents

Polymyxin b analogs for lps detoxification Download PDF

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Publication number
WO2006108586A3
WO2006108586A3 PCT/EP2006/003237 EP2006003237W WO2006108586A3 WO 2006108586 A3 WO2006108586 A3 WO 2006108586A3 EP 2006003237 W EP2006003237 W EP 2006003237W WO 2006108586 A3 WO2006108586 A3 WO 2006108586A3
Authority
WO
WIPO (PCT)
Prior art keywords
lps
dimers
peptide
saep
leu
Prior art date
Application number
PCT/EP2006/003237
Other languages
French (fr)
Other versions
WO2006108586A2 (en
Inventor
Massimo Porro
Tino Krell
Noelle Mistretta
Monique Moreau
Alessandro Rustici
Massimo Velucchi
Original Assignee
Sanofi Pasteur
Biosynth
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.)
Filing date
Publication date
Priority claimed from EP05300270A external-priority patent/EP1712559A1/en
Priority to NZ561374A priority Critical patent/NZ561374A/en
Priority to CA002603850A priority patent/CA2603850A1/en
Priority to AU2006233634A priority patent/AU2006233634A1/en
Priority to MX2007012457A priority patent/MX2007012457A/en
Priority to JP2008505786A priority patent/JP2008537749A/en
Application filed by Sanofi Pasteur, Biosynth filed Critical Sanofi Pasteur
Priority to EP06724173A priority patent/EP1871787A2/en
Priority to BRPI0610701-0A priority patent/BRPI0610701A2/en
Publication of WO2006108586A2 publication Critical patent/WO2006108586A2/en
Publication of WO2006108586A3 publication Critical patent/WO2006108586A3/en
Priority to IL186322A priority patent/IL186322A0/en
Priority to NO20075753A priority patent/NO20075753L/en

Links

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/02—Antidotes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof

Abstract

The invention relates to SAEP II peptide dimers that mimic polymyxin B i.a. in its ability to bind non-covalently the lipopolysaccharide (LPS) of Gram-negative bacteria with high affinity, and therefore to detoxify LPS as polymyxin B does. The dimeric structure is maintained by a pair of disulphide bonds involving the two cystein residues present in the peptide sequence, which does not exceed 17 amino acids and essentially comprises cationic and hydrophobic amino acid residues. In the dimers of the invention, peptides may have a parallel or anti-parallel orientation. As a matter of example, a dimer of the invention is constituted by a peptide of formula NH2-Lys-Thr-Lys-Cysl-Lys-Phe-Leu- Leu-Leu-Cys2-COOH, either in a parallel or antiparallel dimeric form. SAEP II dimers are useful for treating or preventing septic shock and related disorders generated by Gram-negative bacteria infection. The invention also relates to LPS-peptide complexes in which LPS and SAEP II dimers are non-covalently bound together. These complexes are useful as vaccinal agents against Gram-negative bacteria infection.
PCT/EP2006/003237 2005-04-11 2006-04-10 Polymyxin b analogs for lps detoxification WO2006108586A2 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
BRPI0610701-0A BRPI0610701A2 (en) 2005-04-11 2006-04-10 saep ii peptide dimer, composition containing it, its use, lps-peptide complex, its use, pharmaceutical composition and process for its preparation, process for detoxifying one lps of gram-negative bacteria and process for the preparation of a parallel and antiparallel peptide dimer saep ii
CA002603850A CA2603850A1 (en) 2005-04-11 2006-04-10 Polymyxin b analogs for lps detoxification
AU2006233634A AU2006233634A1 (en) 2005-04-11 2006-04-10 Polymyxin B analogs for LPS detoxification
MX2007012457A MX2007012457A (en) 2005-04-11 2006-04-10 Polymyxin b analogs for lps detoxification.
JP2008505786A JP2008537749A (en) 2005-04-11 2006-04-10 Polymyxin B analog for LPS detoxification
NZ561374A NZ561374A (en) 2005-04-11 2006-04-10 Polymyxin B analogs for LPS detoxification
EP06724173A EP1871787A2 (en) 2005-04-11 2006-04-10 Polymyxin b analogs for lps detoxification
IL186322A IL186322A0 (en) 2005-04-11 2007-09-25 Polymyxin b analogs for lps detoxification
NO20075753A NO20075753L (en) 2005-04-11 2007-11-09 Polymyxin B analogs for LPS detoxification

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP05300270.5 2005-04-11
EP05300270A EP1712559A1 (en) 2005-04-11 2005-04-11 Polymyxin B analogs for LPS detoxification
EP05300319 2005-04-26
EP05300319.0 2005-04-26

Publications (2)

Publication Number Publication Date
WO2006108586A2 WO2006108586A2 (en) 2006-10-19
WO2006108586A3 true WO2006108586A3 (en) 2006-12-14

Family

ID=36968822

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/003237 WO2006108586A2 (en) 2005-04-11 2006-04-10 Polymyxin b analogs for lps detoxification

Country Status (11)

Country Link
EP (1) EP1871787A2 (en)
JP (1) JP2008537749A (en)
KR (1) KR20070118646A (en)
AU (1) AU2006233634A1 (en)
BR (1) BRPI0610701A2 (en)
CA (1) CA2603850A1 (en)
IL (1) IL186322A0 (en)
MX (1) MX2007012457A (en)
NO (1) NO20075753L (en)
NZ (1) NZ561374A (en)
WO (1) WO2006108586A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5275982B2 (en) 2006-06-12 2013-08-28 グラクソスミスクライン バイオロジカルズ ソシエテ アノニム vaccine
EP2429658B1 (en) 2009-05-14 2016-04-20 Sanofi Pasteur Method for adjuvating the lipopolysaccharide (LPS) of gram-negative bacteria
EP2430151B1 (en) 2009-05-14 2014-06-18 Sanofi Pasteur Meningococcal vaccine constituted of lipooligosaccharides from modified immunotype l6 neisseria meninigitidis
TWI548746B (en) * 2009-08-06 2016-09-11 英特威特國際股份有限公司 A vaccine directed against porcine pleuropneumonia and a method to obtain such a vaccine
AR113430A1 (en) * 2017-12-22 2020-04-29 Hanmi Pharm Ind Co Ltd THERAPEUTIC ENZYMATIC FUSION PROTEIN THAT HAS A NEW STRUCTURE AND ITS USE
WO2021187928A1 (en) * 2020-03-20 2021-09-23 단디바이오사이언스 주식회사 Composition and kit for removing lipopolysaccharide

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993014115A1 (en) * 1992-01-16 1993-07-22 Massimo Porro Synthetic peptides for detoxification of bacterial endotoxins and treatment of septic shock
WO2004052394A1 (en) * 2002-12-06 2004-06-24 Biosynth S.R.L. Broad-spectrum lps based vaccines of unencapsulated strains of haemophilus influenzae and other pathogenic species of gram-negative bacteria

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993014115A1 (en) * 1992-01-16 1993-07-22 Massimo Porro Synthetic peptides for detoxification of bacterial endotoxins and treatment of septic shock
WO2004052394A1 (en) * 2002-12-06 2004-06-24 Biosynth S.R.L. Broad-spectrum lps based vaccines of unencapsulated strains of haemophilus influenzae and other pathogenic species of gram-negative bacteria

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DEMITRI M T ET AL: "INHIBITION OF LPS-INDUCED SYSTEMIC AND LOCAL TNF PRODUCTION BY A SYNTHETIC ANTI-ENDOTOXIN PEPTIDE (SAEP-2)", JOURNAL OF ENDOTOXIN RESEARCH, CHURCHILL LIVINGSTONE, EDINBURGH, GB, vol. 3, no. 6, December 1996 (1996-12-01), pages 445 - 454, XP009001817, ISSN: 0968-0519 *
RUSTICI A ET AL: "MOLECULAR MAPPING AND DETOXIFICATION OF THE LIPID A BINDING SITE BYSYNTHETIC PEPTIDES", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE,, US, vol. 259, no. 5093, 15 January 1993 (1993-01-15), pages 361 - 365, XP000608499, ISSN: 0036-8075 *

Also Published As

Publication number Publication date
KR20070118646A (en) 2007-12-17
CA2603850A1 (en) 2006-10-19
BRPI0610701A2 (en) 2010-07-20
AU2006233634A1 (en) 2006-10-19
WO2006108586A2 (en) 2006-10-19
NO20075753L (en) 2007-11-09
IL186322A0 (en) 2008-01-20
MX2007012457A (en) 2007-12-10
NZ561374A (en) 2009-02-28
EP1871787A2 (en) 2008-01-02
JP2008537749A (en) 2008-09-25

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