WO2009027707A3 - Methods for preparing peptides, especially radio-labelled peptides - Google Patents

Methods for preparing peptides, especially radio-labelled peptides Download PDF

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Publication number
WO2009027707A3
WO2009027707A3 PCT/GB2008/002951 GB2008002951W WO2009027707A3 WO 2009027707 A3 WO2009027707 A3 WO 2009027707A3 GB 2008002951 W GB2008002951 W GB 2008002951W WO 2009027707 A3 WO2009027707 A3 WO 2009027707A3
Authority
WO
WIPO (PCT)
Prior art keywords
peptides
methods
amino acid
substituted amino
labelled
Prior art date
Application number
PCT/GB2008/002951
Other languages
French (fr)
Other versions
WO2009027707A2 (en
Inventor
Stefano Carlo Giorgio Biagini
Phillip John Blower
Alison Parry
Gareth E Smith
Original Assignee
Univ Kent Canterbury
Stefano Carlo Giorgio Biagini
Phillip John Blower
Alison Parry
Gareth E Smith
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 Univ Kent Canterbury, Stefano Carlo Giorgio Biagini, Phillip John Blower, Alison Parry, Gareth E Smith filed Critical Univ Kent Canterbury
Publication of WO2009027707A2 publication Critical patent/WO2009027707A2/en
Publication of WO2009027707A3 publication Critical patent/WO2009027707A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/13—Labelling of peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/008—Peptides; Proteins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • C07K14/595—Gastrins; Cholecystokinins [CCK]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Endocrinology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Analytical Chemistry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The invention provides a substituted amino acid comprising an optionally protected primary or secondary amino group, a carboxylic acid group and a group capable of binding a fluoride ion; a peptide comprising the substituted amino acid; a method for the preparation of the peptide and its use in diagnosis. The substituted amino acid according to the invention permits a synthetic approach with greater flexibility and control of the site of labelling than conventional methods.
PCT/GB2008/002951 2007-08-31 2008-08-29 Methods for preparing peptides, especially radio-labelled peptides WO2009027707A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0716799.2 2007-08-31
GB0716799A GB0716799D0 (en) 2007-08-31 2007-08-31 Improvements in or relating to radio-labelled peptides

Publications (2)

Publication Number Publication Date
WO2009027707A2 WO2009027707A2 (en) 2009-03-05
WO2009027707A3 true WO2009027707A3 (en) 2009-04-16

Family

ID=38616936

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2008/002951 WO2009027707A2 (en) 2007-08-31 2008-08-29 Methods for preparing peptides, especially radio-labelled peptides

Country Status (2)

Country Link
GB (1) GB0716799D0 (en)
WO (1) WO2009027707A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0914543D0 (en) 2009-08-20 2009-09-30 Ge Healthcare Ltd Radioiodination method
CA2885305C (en) * 2012-10-12 2019-11-12 Spirogen Sarl Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation
CN107098924A (en) * 2017-05-19 2017-08-29 暨南大学 A kind of amino acid derivativges of aryl-boric acid ester modification and preparation method and application

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5276170A (en) * 1992-01-16 1994-01-04 The United States Of America As Represented By The Department Of Health And Human Services Azido-substituted aromatic amino acids
JPH08225574A (en) * 1994-12-21 1996-09-03 Takeda Chem Ind Ltd Anti-protozoan preparation
US20040259164A1 (en) * 2003-06-06 2004-12-23 President And Fellows Of Harvard College Capture and release based isotope tagged peptides and methods for using the same
US20050004009A1 (en) * 2003-02-20 2005-01-06 James Turkson Peptidomimetic inhibitors of STAT activity and uses thereof
EP1908472A1 (en) * 2006-10-02 2008-04-09 Bayer Schering Pharma Aktiengesellschaft Silicon derivatives for PET imaging
EP1911452A1 (en) * 2006-10-11 2008-04-16 Bayer Schering Pharma Aktiengesellschaft Silicon-derivates for PET-Imaging
EP1970064A1 (en) * 2007-03-12 2008-09-17 Bayer Schering Pharma Aktiengesellschaft Silicon-derivatives for pet-imaging

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5276170A (en) * 1992-01-16 1994-01-04 The United States Of America As Represented By The Department Of Health And Human Services Azido-substituted aromatic amino acids
JPH08225574A (en) * 1994-12-21 1996-09-03 Takeda Chem Ind Ltd Anti-protozoan preparation
US20050004009A1 (en) * 2003-02-20 2005-01-06 James Turkson Peptidomimetic inhibitors of STAT activity and uses thereof
US20040259164A1 (en) * 2003-06-06 2004-12-23 President And Fellows Of Harvard College Capture and release based isotope tagged peptides and methods for using the same
EP1908472A1 (en) * 2006-10-02 2008-04-09 Bayer Schering Pharma Aktiengesellschaft Silicon derivatives for PET imaging
EP1911452A1 (en) * 2006-10-11 2008-04-16 Bayer Schering Pharma Aktiengesellschaft Silicon-derivates for PET-Imaging
EP1970064A1 (en) * 2007-03-12 2008-09-17 Bayer Schering Pharma Aktiengesellschaft Silicon-derivatives for pet-imaging

Non-Patent Citations (16)

* Cited by examiner, † Cited by third party
Title
AMSSOMS K ET AL: "Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase. Part 1: Substitution of the glycine carboxylic acid group", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 8, 16 September 2002 (2002-09-16), pages 2553 - 2556, XP009110216, ISSN: 0960-894X *
ANDRUSZKIEWICZ R ET AL: "Structural determinants of inhibitory activity of N3-(4-methoxyfumaroyl)-L-2,3- diaminopropanoic acid towards glucosamine-6-phosphate synthase", POLISH JOURNAL OF CHEMISTRY, vol. 67, no. 4, April 1993 (1993-04-01), pages 673 - 683, XP000964579 *
BALDWIN ET AL: "Synthesis of chiral isoxazolidin-5-ones and their applications to the synthesis of beta-amino-alanines and beta-(N-hydroxyamino)-alanines", TETRAHEDRON, vol. 50, no. 17, 1994, pages 5049 - 5066, XP002094735, ISSN: 0040-4020 *
BALDWIN J E ET AL: "Synthesis of L-beta isoxazolin-5-one-2-ylalanine a novel method for the synthesis of N-substituted 3,4-unsubstituted isoxazolin-5-ones", TETRAHEDRON LETTERS, vol. 26, no. 48, 1985, pages 5931 - 5934, XP009111642, ISSN: 0040-4039 *
FEDOROV A Y ET AL: "Synthesis of (azidomethyl)phenylboronic acids", RUSSIAN CHEMICAL BULLETIN, vol. 53, no. 2, February 2004 (2004-02-01), pages 370 - 375, XP007907044, ISSN: 1066-5285 *
GOPALSAMY A ET AL: "Parallel solid-phase synthesis of vitronectin receptor (alphavbeta3) inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 10, no. 15, 7 August 2000 (2000-08-07), pages 1715 - 1718, XP004213230, ISSN: 0960-894X *
ITOH F ET AL: "Non-glutamate type pyrrolo[2,3-d]pyrimidine antifolates. II. Synthesis and antitumor activity of N5-substituted glutamine analogs", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 44, no. 8, 1996, pages 1498 - 1509, XP001018999, ISSN: 0009-2363 *
JEGO J M ET AL: "A simple convenient preparation of omega-aminoboronic acids and esters", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 435, no. 1-2, 5 February 1992 (1992-02-05), pages 1 - 8, XP007907042, ISSN: 0022-328X *
LACHANCE B ET AL: "Synthesis and evaluation of potential glutamine antagonists", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 22, no. 3, May 1987 (1987-05-01), pages 179 - 186, XP023870990, ISSN: 0223-5234 *
LAUS G ET AL: "Facile Synthesis of New Areneboronates as Terminal Ethyne Monomers", MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY, vol. 137, no. 1, January 2006 (2006-01-01), pages 69 - 75, XP019378855, ISSN: 1434-4475 *
MANGOLD J B ET AL: "Azidoalanine mutagenicity in Salmonella: Effect of homologation and alpha-methyl substitution", MUTATION RESEARCH, vol. 216, no. 1, February 1989 (1989-02-01), pages 27 - 33, XP023456042, ISSN: 0165-1161 *
MATSUDA T ET AL: "Ruthenium-catalysed double trans-hydrosilylation of 1,4-diarylbuta-1,3-diynes leading to 2,5-diarylsiloles", CHEMICAL COMMUNICATIONS, no. 25, 7 July 2007 (2007-07-07), pages 2627 - 2629, XP009111668, ISSN: 1359-7345 *
ROSOWSKY A ET AL: "Synthesis and Biological Activity of Methotrexate Analogues with Two Acid groups and a Hydrophobic Aromatic Ring in the side Chain", JOURNAL OF MEDICINAL CHEMISTRY, vol. 34, no. 2, 1991, pages 574 - 579, XP002291411, ISSN: 0022-2623 *
ROY B C ET AL: "Polymerized fluorescent liposomes incorporating lanthanide ions", ORGANIC LETTERS, vol. 2, no. 20, 5 October 2000 (2000-10-05), pages 3067 - 3070, XP009111644, ISSN: 1523-7060 *
SCHIRRMACHER R ET AL: "18F-labeling of peptides by means of an organosilicon-based fluoride acceptor", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 45, no. 36, 11 September 2006 (2006-09-11), pages 6047 - 6050, XP009111737, ISSN: 1433-7851 *
ZHENG S L ET AL: "Microwave-assisted synthesis of ethynylarylboronates for the construction of boronic acid-based fluorescent sensors for carbohydrates", TETRAHEDRON LETTERS, vol. 47, no. 14, 3 April 2006 (2006-04-03), pages 2331 - 2335, XP025003833, ISSN: 0040-4039 *

Also Published As

Publication number Publication date
GB0716799D0 (en) 2007-10-10
WO2009027707A2 (en) 2009-03-05

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