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WO1999003488A3 - Biologically active peptides with reduced toxicity in animals and a method for preparing same - Google Patents

Biologically active peptides with reduced toxicity in animals and a method for preparing same Download PDF

Info

Publication number
WO1999003488A3
WO1999003488A3 PCT/US1998/014610 US9814610W WO9903488A3 WO 1999003488 A3 WO1999003488 A3 WO 1999003488A3 US 9814610 W US9814610 W US 9814610W WO 9903488 A3 WO9903488 A3 WO 9903488A3
Authority
WO
WIPO (PCT)
Prior art keywords
biologically active
peptides
reduced toxicity
animals
hydrogen
Prior art date
Application number
PCT/US1998/014610
Other languages
French (fr)
Other versions
WO1999003488A2 (en
Inventor
U Prasad Kari
Taffy J Williams
Michael Mclane
Original Assignee
Magainin Pharma
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
Application filed by Magainin Pharma filed Critical Magainin Pharma
Priority to JP2000502785A priority Critical patent/JP2001510164A/en
Priority to AU83005/98A priority patent/AU8300598A/en
Priority to CA002294518A priority patent/CA2294518A1/en
Priority to EP98933343A priority patent/EP1001800A2/en
Publication of WO1999003488A2 publication Critical patent/WO1999003488A2/en
Publication of WO1999003488A3 publication Critical patent/WO1999003488A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/43504—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from invertebrates
    • C07K14/43563—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from invertebrates from insects
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Zoology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Genetics & Genomics (AREA)
  • Toxicology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biochemistry (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Insects & Arthropods (AREA)
  • Communicable Diseases (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The present invention relates to biologically active peptides with reduced toxicity and methods of preparing them. The peptides of the invention, which can be unsubstituted or N-terminal substituted have formula (I), wherein X is a biologically active amphiphilic ion channel-forming peptide or protein, T is a lipophilic moiety or hydrogen, and W is T or hydrogen. Preferably T is formula (II), wherein R is a hydrocarbon (alkyl or aromatic or alkylaromatic) having at least 2 and no more than 10 carbon atoms. T is preferably an octanoyl group. The peptides and proteins of the invention have improved antimicrobial and anti-tumor biological activity while exhibiting reduced toxicity. A preferred method of reducing toxicity involves the formation of related methane sulfonate derivatives or analogues. Additionally, the compounds of the invention may be used to treat sepsis, septic shock, and lung infections, such as those occuring in cystic fibrosis.
PCT/US1998/014610 1997-07-15 1998-07-15 Biologically active peptides with reduced toxicity in animals and a method for preparing same WO1999003488A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2000502785A JP2001510164A (en) 1997-07-15 1998-07-15 A bioactive peptide having reduced toxicity to animals and a method for preparing the same.
AU83005/98A AU8300598A (en) 1997-07-15 1998-07-15 Biologically active peptides with reduced toxicity in animals and a method for preparing same
CA002294518A CA2294518A1 (en) 1997-07-15 1998-07-15 Biologically active peptides with reduced toxicity in animals and a method for preparing same
EP98933343A EP1001800A2 (en) 1997-07-15 1998-07-15 Biologically active peptides with reduced toxicity in animals and a method for preparing same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US89300697A 1997-07-15 1997-07-15
US08/893,006 1997-07-15

Publications (2)

Publication Number Publication Date
WO1999003488A2 WO1999003488A2 (en) 1999-01-28
WO1999003488A3 true WO1999003488A3 (en) 1999-04-08

Family

ID=25400865

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/014610 WO1999003488A2 (en) 1997-07-15 1998-07-15 Biologically active peptides with reduced toxicity in animals and a method for preparing same

Country Status (5)

Country Link
EP (1) EP1001800A2 (en)
JP (1) JP2001510164A (en)
AU (1) AU8300598A (en)
CA (1) CA2294518A1 (en)
WO (1) WO1999003488A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008140834A2 (en) * 2007-01-16 2008-11-20 The Regents Of The University Of California Novel antimicrobial peptides
US7960336B2 (en) * 2007-08-03 2011-06-14 Pharmain Corporation Composition for long-acting peptide analogs
JP5616233B2 (en) 2008-01-24 2014-10-29 エスペランス ファーマシューティカルズＥｓｐｅｒａｎｃｅ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Lysis domain fusion construct and methods for its generation and use
KR20210090298A (en) 2012-10-30 2021-07-19 에스퍼란스 파마슈티컬스, 인코포레이티드 Antibody/drug conjugates and methods of use

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024138A1 (en) * 1992-06-01 1993-12-09 Magainin Pharmaceuticals, Inc. Biologically active peptides having n-terminal substitutions
WO1995019370A1 (en) * 1994-01-18 1995-07-20 Magainin Pharmaceuticals Inc. Ion-channel forming amphiphilic peptides having n-terminal modifications

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024138A1 (en) * 1992-06-01 1993-12-09 Magainin Pharmaceuticals, Inc. Biologically active peptides having n-terminal substitutions
WO1995019370A1 (en) * 1994-01-18 1995-07-20 Magainin Pharmaceuticals Inc. Ion-channel forming amphiphilic peptides having n-terminal modifications

Also Published As

Publication number Publication date
AU8300598A (en) 1999-02-10
CA2294518A1 (en) 1999-01-28
JP2001510164A (en) 2001-07-31
WO1999003488A2 (en) 1999-01-28
EP1001800A2 (en) 2000-05-24

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