WO1989001489A1 - Regulation de l'angiogenese et compositions et procedes prevus a cet effet - Google Patents

Regulation de l'angiogenese et compositions et procedes prevus a cet effet Download PDF

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Publication number
WO1989001489A1
WO1989001489A1 PCT/AU1988/000300 AU8800300W WO8901489A1 WO 1989001489 A1 WO1989001489 A1 WO 1989001489A1 AU 8800300 W AU8800300 W AU 8800300W WO 8901489 A1 WO8901489 A1 WO 8901489A1
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WO
WIPO (PCT)
Prior art keywords
tyr
gly
acm
peptide
angiogenesis
Prior art date
Application number
PCT/AU1988/000300
Other languages
English (en)
Inventor
Brian Richard Mcauslan
Original Assignee
Commonwealth Scientific And Industrial Research Or
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 Commonwealth Scientific And Industrial Research Or filed Critical Commonwealth Scientific And Industrial Research Or
Publication of WO1989001489A1 publication Critical patent/WO1989001489A1/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K14/00Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/475Growth factors; Growth regulators
    • C07K14/485Epidermal growth factor [EGF], i.e. urogastrone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides

Definitions

  • Angiogenesis is the development of blood vessels.
  • agents which will permit control of angiogenesis is of considerable interest in medical science and to associated industries; substances which stimulate angiogenesis may, for instance, have value in promoting wound healing, while inhibitors of angiogenesis could find application for retarding tumor growth or blocking the onset of diabetic blindness.
  • Angiogenic properties are exhibited by a variety of agents.
  • agents such as extracts of carcinoma cells or of normal bovine parotid glands; partially purified fractions of substances from Walker carcinoma cells, bovine parotid cells or bovine liver have been shown to be angiogenic by occular implant and chick chorioallantoic membrane assays. It has also been shown that low concentrations of ' copper ions can induce neovascularisation in the anterior eye chamber or corneal pocket.
  • EGF epidermal growth factor
  • a method for stimulating angiogenesis in animals characterised by the step of administering to an animal an effective amount of an angiogenically stimulating synthetic peptide having an amino acid sequence substantially corresponding to an amino acid sequence occurring in EGF, excluding EGF.
  • amino acid is to be understood to embrace amino acid substitutes as recognized in the art.
  • the present invention provides a synthetic peptide, which is active in stimulating angiogenesis in animals, having an amino acid sequence substantially corresponding to an amino acid sequence occurring in epidermal growth factor (EGF), excluding EGF.
  • EGF epidermal growth factor
  • the present invention provides a composition for use in the stimulation of angiogenesis comprising an effective amount of a synthetic peptide, which is active in stimulating angiongenesis, having an amino acid sequence substantially corresponding to an amino acid sequence occurring in epidermal growth factor (EGF), excluding EGF, and a pharmaceutically acceptable carrier.
  • the active sequences may be identified using a cell migration assay as a screen system, together with an in vivo assay that minimises inflammation.
  • the present inventor has using these techniques, identified synthetic peptide known amino acid sequences that induce angiogenesis by a medium involving (or consistent with) direct action on endothelial cells.
  • the amino acid sequence for naturally occurring EGF is shown in Figure 1. Those sequences identified as active are: 3 - 14 3 - 10 12 - 14 12 - 15 29 - 37 33 - 37 Analogues or derivatives of these sequences, including small sub-fragments are also included in the scope of the invention.
  • a line of capillary endothelial cells free from neural cells was prepared from bovine retinas McAuslan et al 1986 (In Vitro Models for Cancer Research. Chemical Rubber Co.
  • Epidermal Growth Factor was used in the form described by McAuslan 1985 (Cell Biol. Int. Reports 9 ⁇
  • EGF fragments were synthesised using a combined chemical-enzyme procedure described by Widmer et al in
  • Oet oxyethyl ester
  • ACM aceto amido methyl.
  • BOC tertiary butyl oxycarbonyl.
  • NH 2 amide on a carboxyl terminal group.
  • BZ benzoyl. and conventional abbreviations are used for amino acid moieties.
  • the angiogenic compounds according to this invention may find application in a variety of clinical fields. They may be used, for instance to enhance the healing of burns and wounds (especially those involving tissue defects); ( ⁇ ) to promote the acceptance of skin or organ grafts; (iii) in reconstructive and cosmetic surgery (including subdermal implants); and (iv) in prosthetic surgery, particularly where involved in vascular prosthesis.
  • the compounds may be administered singly, in association with each or in association with angiogenic stimulator in different molecular species. Additionally, they are suitable for release from biodegradable matrices and by slow-release techniques.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Zoology (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Toxicology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Des peptides synthétiques, qui ont une action de stimulation de l'angiogenèse chez les animaux, comportent des séquences correspondant sensiblement aux séquences d'acides aminés présentes dans le facteur de la croissance épidermique. Des compositions contenant ces peptides synthétiques et un procédé de stimulation de l'angiogenèse chez les animaux sont également décrits.
PCT/AU1988/000300 1987-08-10 1988-08-10 Regulation de l'angiogenese et compositions et procedes prevus a cet effet WO1989001489A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPI3629 1987-08-10
AU362987 1987-08-10

Publications (1)

Publication Number Publication Date
WO1989001489A1 true WO1989001489A1 (fr) 1989-02-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU1988/000300 WO1989001489A1 (fr) 1987-08-10 1988-08-10 Regulation de l'angiogenese et compositions et procedes prevus a cet effet

Country Status (1)

Country Link
WO (1) WO1989001489A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992003476A1 (fr) * 1990-08-13 1992-03-05 Board Of Regents, The University Of Texas System Peptides de facteur de croissance epidermique biologiquement actifs favorisant la regeneration tissulaire et le traitement du cancer
WO2000037095A1 (fr) * 1998-12-21 2000-06-29 The Victor Chang Cardiac Research Institute Fonction et manipulation du muscle cardiaque
US7662772B2 (en) 1999-04-23 2010-02-16 Acorda Therapeutics, Inc. Methods for treating congestive heart failure
US7795212B2 (en) 2002-05-24 2010-09-14 Zensun (Shanghai) Science & Technology Limited Neuregulin based methods and compositions for treating cardiovascular diseases
US8476405B2 (en) 2005-12-02 2013-07-02 Zensun (Shanghai) Science & Technology Ltd. Neuregulin variants and methods of screening and using thereof
US10561709B2 (en) 2014-10-17 2020-02-18 Zensun (Shanghai) Science & Technology, Co., Ltd. Methods and compositions of neuregulins for preventing, treating or delaying preserved ejection fraction cardiac failure
US10702585B2 (en) 2014-01-03 2020-07-07 Zensun (Shanghai) Science & Technology, Co., Ltd. Formula of neuregulin preparation
US11179323B2 (en) 2013-05-22 2021-11-23 Zensun (Shanghai) Science & Technology, Co., Ltd. Extended release of neuregulin for treating heart failure
US11253573B2 (en) 2011-10-10 2022-02-22 Zensun (Shanghai) Science & Technology, Co., Ltd. Compositions and methods for treating heart failure
US11638746B2 (en) 2005-12-30 2023-05-02 Zensun (Shanghai) Science & Technology, Co., Ltd. Extended release of neuregulin for improved cardiac function

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917824A (en) * 1973-03-28 1975-11-04 Ici Ltd Pharmaceutical compositions containing epidermal growth factor or closely related derivatives thereof for inhibiting the secretion of acidic gastric juice in warm blooded animals
US3948875A (en) * 1973-11-27 1976-04-06 Stanley Cohen Process for the preparation of epidermal growth factor and new derivative using cross-linked polyacrylamide gel at a pH of 1-3
JPS5927858A (ja) * 1982-08-05 1984-02-14 Nippon Shinyaku Co Ltd ポリペプチドの製法
US4490365A (en) * 1980-08-04 1984-12-25 Commonwealth Scientifique & Industrial Research Organization Defleecing compounds
WO1985000369A1 (fr) * 1983-07-05 1985-01-31 Chiron Corporation Synthese a l'aide d'adn hybride du facteur de croissance epidermique
AU3439084A (en) * 1983-09-14 1985-04-11 Komoriya, A. Synthetic peptides with egf like activity and pharmaceutical compositions and methods of use
EP0205051A1 (fr) * 1985-05-30 1986-12-17 ZAMBON S.p.A. Composition pharmaceutique sous forme d'une pommade pour application dermique et ophtalmique
JPS6217402A (ja) * 1985-07-12 1987-01-26 ヴイツカ−ズ,インコ−ポレ−テツド 油圧制御装置
JPS62149622A (ja) * 1985-12-24 1987-07-03 Wakunaga Pharmaceut Co Ltd 腸機能改善剤
US4686283A (en) * 1985-04-16 1987-08-11 Syntex (U.S.A.) Inc. Analogs of transforming and epidermal growth factor fragments for therapy and diagnosis
JPS633791A (ja) * 1986-06-25 1988-01-08 Hitachi Ltd プラスミド組換え体
JPS6377823A (ja) * 1986-09-19 1988-04-08 Fujisawa Pharmaceut Co Ltd 抗癌剤
US4743679A (en) * 1986-02-24 1988-05-10 Creative Biomolecules, Inc. Process for producing human epidermal growth factor and analogs thereof
EP0224885B1 (fr) * 1985-11-28 1992-05-20 Wakunaga Seiyaku Kabushiki Kaisha Composition antitumorale.

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917824A (en) * 1973-03-28 1975-11-04 Ici Ltd Pharmaceutical compositions containing epidermal growth factor or closely related derivatives thereof for inhibiting the secretion of acidic gastric juice in warm blooded animals
US3948875A (en) * 1973-11-27 1976-04-06 Stanley Cohen Process for the preparation of epidermal growth factor and new derivative using cross-linked polyacrylamide gel at a pH of 1-3
US4490365A (en) * 1980-08-04 1984-12-25 Commonwealth Scientifique & Industrial Research Organization Defleecing compounds
JPS5927858A (ja) * 1982-08-05 1984-02-14 Nippon Shinyaku Co Ltd ポリペプチドの製法
WO1985000369A1 (fr) * 1983-07-05 1985-01-31 Chiron Corporation Synthese a l'aide d'adn hybride du facteur de croissance epidermique
AU3439084A (en) * 1983-09-14 1985-04-11 Komoriya, A. Synthetic peptides with egf like activity and pharmaceutical compositions and methods of use
US4686283A (en) * 1985-04-16 1987-08-11 Syntex (U.S.A.) Inc. Analogs of transforming and epidermal growth factor fragments for therapy and diagnosis
EP0205051A1 (fr) * 1985-05-30 1986-12-17 ZAMBON S.p.A. Composition pharmaceutique sous forme d'une pommade pour application dermique et ophtalmique
JPS6217402A (ja) * 1985-07-12 1987-01-26 ヴイツカ−ズ,インコ−ポレ−テツド 油圧制御装置
EP0224885B1 (fr) * 1985-11-28 1992-05-20 Wakunaga Seiyaku Kabushiki Kaisha Composition antitumorale.
JPS62149622A (ja) * 1985-12-24 1987-07-03 Wakunaga Pharmaceut Co Ltd 腸機能改善剤
US4743679A (en) * 1986-02-24 1988-05-10 Creative Biomolecules, Inc. Process for producing human epidermal growth factor and analogs thereof
JPS633791A (ja) * 1986-06-25 1988-01-08 Hitachi Ltd プラスミド組換え体
JPS6377823A (ja) * 1986-09-19 1988-04-08 Fujisawa Pharmaceut Co Ltd 抗癌剤

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DERWENT WPI/L ONLINE ABSTRACT ACCESSION NO. 88-046257/07; & JP,A,63 003 791 (HITACHI K.K. AND HITACHI CHEMICAL K.K.), 8 January 1988 (08.01.88). *
DERWENT WPI/L ONLINE ABSTRACT ACCESSION NO. 88-136324/20; & JP,A,63 077 823 (FUJISAWA PHARM K.K.), 8 April 1988 (08.04.88). *
PATENT ABSTRACTS OF JAPAN, C-225, page 70; & JP,A,59 027 858 (NIPPON SHINYAKU K.K.; YAJIMA, H.), 14 February 1984 (14.02.84). *
PATENT ABSTRACTS OF JAPAN, C-463, page 118; & JP,A,62 149 622 (WAKUNAGA PHARMACEUT CO LTD; UDA, N.), 3 July 1987 (03.07.87). *
PATENT ABSTRACTS OF JAPAN, C-470, page 12; & JP,A,62 017 402 (WAKUNAGA PHARMACEUT CO LTD; KAKIMOTO, M.), 30 July 1987 (30.07.87). *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992003476A1 (fr) * 1990-08-13 1992-03-05 Board Of Regents, The University Of Texas System Peptides de facteur de croissance epidermique biologiquement actifs favorisant la regeneration tissulaire et le traitement du cancer
WO2000037095A1 (fr) * 1998-12-21 2000-06-29 The Victor Chang Cardiac Research Institute Fonction et manipulation du muscle cardiaque
US7226907B1 (en) 1998-12-21 2007-06-05 Zensun (Shanghai) Science & Technology Limited Cardiac muscle function and manipulation
US7612164B2 (en) 1998-12-21 2009-11-03 Zensun (Shanghai) Science and Technologies Ltd. Cardiac muscle function and manipulation
US7964555B2 (en) 1998-12-21 2011-06-21 Zensun (Shanghai) Sci & Tech Co., Ltd. Cardiac muscle function and manipulation
US7662772B2 (en) 1999-04-23 2010-02-16 Acorda Therapeutics, Inc. Methods for treating congestive heart failure
US10232016B2 (en) 1999-04-23 2019-03-19 Acorda Therapeutics, Inc. Methods for treating congestive heart failure
US8076283B2 (en) 1999-04-23 2011-12-13 Acorda Therapeutics, Inc. Methods for treating congestive heart failure
US8394761B2 (en) 1999-04-23 2013-03-12 Beth Israel Deaconess Medical Center Methods for treating congestive heart failure
US8785387B2 (en) 2002-05-24 2014-07-22 Zensun (Shanghai) Science & Technology Limited Neuregulin based methods and compositions for treating cardiovascular disease
US9555076B2 (en) 2002-05-24 2017-01-31 Zensun (Shanghai) Science & Technology, Co., Ltd. Neuregulin based methods and compositions for treating cardiovascular diseases
US7795212B2 (en) 2002-05-24 2010-09-14 Zensun (Shanghai) Science & Technology Limited Neuregulin based methods and compositions for treating cardiovascular diseases
US8476405B2 (en) 2005-12-02 2013-07-02 Zensun (Shanghai) Science & Technology Ltd. Neuregulin variants and methods of screening and using thereof
US9340597B2 (en) 2005-12-02 2016-05-17 Zensun (Shanghai) Science And Technology Ltd. Neuregulin variants and methods of screening and using thereof
US10112983B2 (en) 2005-12-02 2018-10-30 Zensun (Shanghai) Science & Technology, Co., Ltd. Neuregulin variants and methods of screening and using thereof
US11638746B2 (en) 2005-12-30 2023-05-02 Zensun (Shanghai) Science & Technology, Co., Ltd. Extended release of neuregulin for improved cardiac function
US11253573B2 (en) 2011-10-10 2022-02-22 Zensun (Shanghai) Science & Technology, Co., Ltd. Compositions and methods for treating heart failure
US11179323B2 (en) 2013-05-22 2021-11-23 Zensun (Shanghai) Science & Technology, Co., Ltd. Extended release of neuregulin for treating heart failure
US10702585B2 (en) 2014-01-03 2020-07-07 Zensun (Shanghai) Science & Technology, Co., Ltd. Formula of neuregulin preparation
US11969458B2 (en) 2014-01-03 2024-04-30 Zensun (Shanghai) Science & Technology, Co., Ltd. Formula of neuregulin preparation
US10561709B2 (en) 2014-10-17 2020-02-18 Zensun (Shanghai) Science & Technology, Co., Ltd. Methods and compositions of neuregulins for preventing, treating or delaying preserved ejection fraction cardiac failure

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