WO1996031531A3 - Fluorescent peptides - Google Patents

Fluorescent peptides Download PDF

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Publication number
WO1996031531A3
WO1996031531A3 PCT/CA1996/000207 CA9600207W WO9631531A3 WO 1996031531 A3 WO1996031531 A3 WO 1996031531A3 CA 9600207 W CA9600207 W CA 9600207W WO 9631531 A3 WO9631531 A3 WO 9631531A3
Authority
WO
WIPO (PCT)
Prior art keywords
peptide
receptor
biologically active
light
emitting moiety
Prior art date
Application number
PCT/CA1996/000207
Other languages
French (fr)
Other versions
WO1996031531A2 (en
Inventor
Clarissa Desjardins
Marie-Pierre Faure
Alain Beaudet
Jean-Pierre Vincent
Georges Gaudriault
Original Assignee
Advanced Bioconcept Ltd
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 US08/416,007 external-priority patent/US5693679A/en
Priority claimed from US08/475,751 external-priority patent/US5824772A/en
Application filed by Advanced Bioconcept Ltd filed Critical Advanced Bioconcept Ltd
Priority to EP96908950A priority Critical patent/EP0820466A2/en
Publication of WO1996031531A2 publication Critical patent/WO1996031531A2/en
Publication of WO1996031531A3 publication Critical patent/WO1996031531A3/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
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • 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
    • C07K14/575—Hormones
    • 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
    • C07K14/575—Hormones
    • C07K14/57536—Endothelin, vasoactive intestinal contractor [VIC]
    • 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
    • C07K14/575—Hormones
    • C07K14/57563—Vasoactive intestinal peptide [VIP]; Related peptides
    • 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
    • C07K7/14—Angiotensins: Related peptides
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
    • G01N33/5094—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for blood cell populations
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/569—Immunoassay; Biospecific binding assay; Materials therefor for microorganisms, e.g. protozoa, bacteria, viruses
    • G01N33/56966—Animal cells

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Cell Biology (AREA)
  • Hematology (AREA)
  • Zoology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Toxicology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Food Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Virology (AREA)
  • Ecology (AREA)
  • Peptides Or Proteins (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

The invention provides biologically active compounds of formula (I) where R1 is a light-emitting moiety and R7 is a peptide of between 2 and 200 amino acids. X is selected from the group including =O, =S, -OH, =C=O, =NH, -H, -OR, -NR, -R, -R3R4, wherein each R, R4 and R3, independently, is H or a C1-C6 branched or unbranched, substituted or unsubstituted, alkyl. The compounds are both biologically active and optically detectable. The peptide is chemically attached to the light-emitting moiety at an amino acid position which is not involved in binding to the peptide's receptor. In this way, the peptide's affinity for its receptor is not significantly decreased, and the compound retains high biological activity and can be easily detected using standard optical means.
PCT/CA1996/000207 1995-04-04 1996-04-04 Fluorescent peptides WO1996031531A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP96908950A EP0820466A2 (en) 1995-04-04 1996-04-04 Fluorescent peptides

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US08/416,007 US5693679A (en) 1995-04-04 1995-04-04 Fluorescent somatostatin
US08/416,007 1995-04-04
US08/475,751 1995-06-07
US08/475,751 US5824772A (en) 1995-04-04 1995-06-07 Fluorescent somatostatin
US50485695A 1995-07-20 1995-07-20
US08/504,856 1995-07-20

Publications (2)

Publication Number Publication Date
WO1996031531A2 WO1996031531A2 (en) 1996-10-10
WO1996031531A3 true WO1996031531A3 (en) 1997-02-20

Family

ID=46202886

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1996/000207 WO1996031531A2 (en) 1995-04-04 1996-04-04 Fluorescent peptides

Country Status (2)

Country Link
EP (1) EP0820466A2 (en)
WO (1) WO1996031531A2 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8921314B2 (en) 2008-10-15 2014-12-30 Angiochem, Inc. Conjugates of GLP-1 agonists and uses thereof
US9161988B2 (en) 2009-07-02 2015-10-20 Angiochem Inc. Multimeric peptide conjugates and uses thereof
US9173891B2 (en) 2009-04-20 2015-11-03 Angiochem, Inc. Treatment of ovarian cancer using an anticancer agent conjugated to an angiopep-2 analog
US9221867B2 (en) 2003-01-06 2015-12-29 Angiochem Inc. Method for transporting a compound across the blood-brain barrier
US9365634B2 (en) 2007-05-29 2016-06-14 Angiochem Inc. Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6054557A (en) * 1995-04-04 2000-04-25 Advanced Bioconcept (1994) Ltd. Fluorescent peptides
US6821952B1 (en) 1995-07-20 2004-11-23 Perkinelmer Las, Inc. Fluorescent vasoactive intestinal peptide (VIP)
CA2301142A1 (en) 1997-08-14 1999-02-25 The Regents Of The University Of California Fluorescent amyloid a.beta. peptides and uses thereof
CN101160403B (en) 2005-02-18 2014-08-13 安吉奥开米公司 Molecules for transporting a compound across the blood-brain barrier
CA2614687C (en) 2005-07-15 2016-03-22 Angiochem Inc. Use of aprotinin polypeptides as carriers in pharmaceutical conjugates
CA2745524C (en) 2008-12-05 2020-06-09 Angiochem Inc. Conjugates of neurotensin or neurotensin analogs and uses thereof
BRPI0922611A2 (en) 2008-12-17 2018-11-06 Angiochem Inc type 1 membrane matrix metalloprotein inhibitors and uses thereof
EP2740726A1 (en) 2012-12-07 2014-06-11 3B Pharmaceuticals GmbH Neurotensin receptor ligands
EP3154638A1 (en) 2014-06-10 2017-04-19 3B Pharmaceuticals GmbH Conjugate comprising a neurotensin receptor ligand and use thereof
EP2954933A1 (en) 2014-06-10 2015-12-16 3B Pharmaceuticals GmbH Conjugate comprising a neurotensin receptor ligand
EP2954934A1 (en) 2014-06-11 2015-12-16 3B Pharmaceuticals GmbH Conjugate comprising a neurotensin receptor ligand and use thereof
ES2826827T3 (en) 2015-06-15 2021-05-19 Angiochem Inc Methods for the treatment of leptomeningeal carcinomatosis
JP6995768B2 (en) * 2016-03-07 2022-02-21 クイデル カーディオバスキュラー インコーポレイテッド Immune assay controls and their use

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046633A (en) * 1974-07-01 1977-09-06 University Of Utah Direct renin assay system and method
DE2702699A1 (en) * 1976-01-24 1977-12-15 Ajinomoto Kk NEW PEPTIDE DERIVATIVES AND METHODS OF MEASURING COLLAGENASE ACTIVITY USING THESE COMPOUNDS
EP0331126A2 (en) * 1988-02-29 1989-09-06 Roche Diagnostics GmbH Process for the determination of a protein according to the principle of fluorescense polarisation immunoassay
EP0466565A1 (en) * 1990-07-05 1992-01-15 Sanofi Kit for the specific determination of Angiotensin II
WO1993004194A1 (en) * 1991-08-13 1993-03-04 Regents Of The University Of Minnesota LABELLED β-AMYLOID PEPTIDE AND ALZHEIMER'S DISEASE DETECTION
EP0606804A2 (en) * 1992-12-30 1994-07-20 McGILL UNIVERSITY Marker for neurotensin receptor
WO1995022341A1 (en) * 1994-02-18 1995-08-24 Mallinckrodt Medical, Inc. Labelled peptide compounds

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046633A (en) * 1974-07-01 1977-09-06 University Of Utah Direct renin assay system and method
DE2702699A1 (en) * 1976-01-24 1977-12-15 Ajinomoto Kk NEW PEPTIDE DERIVATIVES AND METHODS OF MEASURING COLLAGENASE ACTIVITY USING THESE COMPOUNDS
EP0331126A2 (en) * 1988-02-29 1989-09-06 Roche Diagnostics GmbH Process for the determination of a protein according to the principle of fluorescense polarisation immunoassay
EP0466565A1 (en) * 1990-07-05 1992-01-15 Sanofi Kit for the specific determination of Angiotensin II
WO1993004194A1 (en) * 1991-08-13 1993-03-04 Regents Of The University Of Minnesota LABELLED β-AMYLOID PEPTIDE AND ALZHEIMER'S DISEASE DETECTION
EP0606804A2 (en) * 1992-12-30 1994-07-20 McGILL UNIVERSITY Marker for neurotensin receptor
WO1995022341A1 (en) * 1994-02-18 1995-08-24 Mallinckrodt Medical, Inc. Labelled peptide compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ZHAO, J.Y. ET AL.: "Attachment of a single fluorescent label to peptides for determination by capillary zone electrophoresis", JOURNAL OF CHROMATOGRAPHY, vol. 608, 11 September 1992 (1992-09-11), AMSTERDAM NL, pages 239 - 242, XP000577264 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9221867B2 (en) 2003-01-06 2015-12-29 Angiochem Inc. Method for transporting a compound across the blood-brain barrier
US9365634B2 (en) 2007-05-29 2016-06-14 Angiochem Inc. Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues
US8921314B2 (en) 2008-10-15 2014-12-30 Angiochem, Inc. Conjugates of GLP-1 agonists and uses thereof
US9173891B2 (en) 2009-04-20 2015-11-03 Angiochem, Inc. Treatment of ovarian cancer using an anticancer agent conjugated to an angiopep-2 analog
US9161988B2 (en) 2009-07-02 2015-10-20 Angiochem Inc. Multimeric peptide conjugates and uses thereof

Also Published As

Publication number Publication date
WO1996031531A2 (en) 1996-10-10
EP0820466A2 (en) 1998-01-28

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