WO2009047728A3 - New s-acyl-glutathione derivatives, their syntesis and use in the treatment of oxidative stress-related diseases - Google Patents

New s-acyl-glutathione derivatives, their syntesis and use in the treatment of oxidative stress-related diseases Download PDF

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Publication number
WO2009047728A3
WO2009047728A3 PCT/IB2008/054146 IB2008054146W WO2009047728A3 WO 2009047728 A3 WO2009047728 A3 WO 2009047728A3 IB 2008054146 W IB2008054146 W IB 2008054146W WO 2009047728 A3 WO2009047728 A3 WO 2009047728A3
Authority
WO
WIPO (PCT)
Prior art keywords
gsh
acyl
oxidative stress
new
syntesis
Prior art date
Application number
PCT/IB2008/054146
Other languages
French (fr)
Other versions
WO2009047728A2 (en
Inventor
Gianfranco Liguri
Original Assignee
Univ Firenze
Gianfranco Liguri
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 Firenze, Gianfranco Liguri filed Critical Univ Firenze
Publication of WO2009047728A2 publication Critical patent/WO2009047728A2/en
Publication of WO2009047728A3 publication Critical patent/WO2009047728A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
    • 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
    • A61K47/54—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 an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

Novel S-acyl gluthatione derivatives are described, in particular S-lauroyl GSH, S- palmitoleoyl GSH, S-linoleoyl GSH, S-linolenoleoyl GSH, S-arachidonoleoyl GSH, and a synthesis method thereof. Thanks to their hydrophobic properties, the new derivatives can cross the cell membranes to release, in the cell, following an enzymatic hydrolysis, GSH and corresponding fatty acids both exploiting protective activity against the cell oxidative stress.
PCT/IB2008/054146 2007-10-12 2008-10-09 New s-acyl-glutathione derivatives, their syntesis and use in the treatment of oxidative stress-related diseases WO2009047728A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITFI2007A000224 2007-10-12
IT000224A ITFI20070224A1 (en) 2007-10-12 2007-10-12 NEW S-ACYL SURFACES OF GLUTATHY, THEIR SYNTHESIS AND USE IN THE TREATMENT OF PATHOLOGIES RELATED TO THE CELL OXIDATIVE STRESS

Publications (2)

Publication Number Publication Date
WO2009047728A2 WO2009047728A2 (en) 2009-04-16
WO2009047728A3 true WO2009047728A3 (en) 2009-07-09

Family

ID=40227501

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2008/054146 WO2009047728A2 (en) 2007-10-12 2008-10-09 New s-acyl-glutathione derivatives, their syntesis and use in the treatment of oxidative stress-related diseases

Country Status (2)

Country Link
IT (1) ITFI20070224A1 (en)
WO (1) WO2009047728A2 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110250157A1 (en) * 2009-12-28 2011-10-13 Perricone Nicholas V Skin Hyperpigmentation Acyl Glutathione Treatments
CA2785633C (en) 2009-12-28 2014-07-15 N.V. Perricone Llc Topical acyl glutathione formulations
US8580742B2 (en) 2010-03-05 2013-11-12 N.V. Perricone Llc Topical glutathione formulations for menopausal skin
US20110160143A1 (en) 2009-12-28 2011-06-30 Perricone Nicholas V Topical Acyl Glutathione Psoriasis Compositions
US8609604B2 (en) 2009-12-28 2013-12-17 N.V. Perricone Llc Methods of improving the appearance of aging skin
US8609618B2 (en) * 2011-03-25 2013-12-17 N.V. Perricone Llc Topical palmitoyl glutathione formulations
ITPO20110021A1 (en) * 2011-11-08 2013-05-09 Enrichetta Fedeli PHARMACEUTICAL COMPOSITION FOR THE PROTECTION OF FABRICS FROM CELLULAR AGING ESPECIALLY CAUSED BY IONIZING RADIATIONS
CA3078006C (en) * 2012-07-10 2022-04-26 Xpd Holdings, Llc Stabilized multi-functional antioxidant compounds and methods of use
ITPO20130001A1 (en) * 2013-01-18 2014-07-19 Solosale S R L PHARMACEUTICAL COMPOSITION CONTAINING GLUTATION THIOESTERS TO INCREASE THE LONGEVITY OF INDIVIDUAL ANIMALS OR HUMANS
CN104072577A (en) * 2014-07-01 2014-10-01 田州益膳（北京）食品有限公司 Method for preparing S-acetyl-L-glutathione
IT201700013599A1 (en) * 2017-02-08 2018-08-08 Solosale Srl Pharmaceutical composition for the prevention and treatment of memory and cognitive deficits related to aging
IT202000009553A1 (en) 2020-04-30 2021-10-30 Innbiotec Pharma S R L PHARMACEUTICAL COMPOSITION OF GLUTATHIONE DERIVATIVES FOR USE IN THE TREATMENT OF RESPIRATORY SYNDROMES

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992000320A1 (en) * 1990-06-26 1992-01-09 Boehringer Mannheim Italia S.P.A. A process for the preparation of glutathione s-acyl derivatives, compounds obtained from said process and an intermediate useful for the preparation thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992000320A1 (en) * 1990-06-26 1992-01-09 Boehringer Mannheim Italia S.P.A. A process for the preparation of glutathione s-acyl derivatives, compounds obtained from said process and an intermediate useful for the preparation thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
FALCK J R ET AL: "Preparation of N-(BOC)-B-t L-glutathione dimethyl and di-tert-butyl esters: Versatile synthetic building blocks", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 15, no. 2, January 2007 (2007-01-01), pages 1062 - 1066, XP005801299, ISSN: 0968-0896 *
PENSALFINI ANNA ET AL: "Protective effect of new S-acylglutathione derivatives against amyloid-induced oxidative stress", FREE RADICAL BIOLOGY & MEDICINE, vol. 44, no. 8, 9 February 2008 (2008-02-09), doi:10.1016/j.freeradbiomed.2008.01.025, pages 1624 - 1636, XP022575894, ISSN: 0891-5849 *
SOGABE MITSURU ET AL: "Study on the synthesis and LC/ESI-MSn analyses of glutathione conjugates of bile acids", PEPTIDE SCIENCE, PROTEIN RESEARCH FOUNDATION, MINOO, JP, no. 43, 2006, pages 295 - 296, XP009110862, ISSN: 1344-7661 *

Also Published As

Publication number Publication date
WO2009047728A2 (en) 2009-04-16
ITFI20070224A1 (en) 2009-04-13

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