دورية أكاديمية
أعرض في EDS

Discovery of Hydrolysis-Resistant Isoindoline N-Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration.

التفاصيل البيبلوغرافية
العنوان: Discovery of Hydrolysis-Resistant Isoindoline N-Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration.
المؤلفون: Lin H; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States., Long JZ; Department of Pathology , Stanford University School of Medicine , Stanford , California 94305 , United States., Roche AM; Departments of Cancer Biology and Cell Biology , Dana-Farber Cancer Institute and Harvard Medical School , Boston , Massachusetts 02215 , United States., Svensson KJ; Department of Pathology , Stanford University School of Medicine , Stanford , California 94305 , United States., Dou FY; Departments of Cancer Biology and Cell Biology , Dana-Farber Cancer Institute and Harvard Medical School , Boston , Massachusetts 02215 , United States., Chang MR; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States., Strutzenberg T; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States., Ruiz C; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States., Cameron MD; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States., Novick SJ; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States., Berdan CA; Departments of Chemistry, Molecular and Cell Biology, and Nutritional Sciences and Toxicology , University of California Berkeley , Berkeley , California 94720 , United States., Louie SM; Departments of Chemistry, Molecular and Cell Biology, and Nutritional Sciences and Toxicology , University of California Berkeley , Berkeley , California 94720 , United States., Nomura DK; Departments of Chemistry, Molecular and Cell Biology, and Nutritional Sciences and Toxicology , University of California Berkeley , Berkeley , California 94720 , United States., Spiegelman BM; Departments of Cancer Biology and Cell Biology , Dana-Farber Cancer Institute and Harvard Medical School , Boston , Massachusetts 02215 , United States., Griffin PR; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States., Kamenecka TM; Department of Molecular Medicine , The Scripps Research Institute , Jupiter , Florida 33458 , United States.
المصدر: Journal of medicinal chemistry [J Med Chem] 2018 Apr 12; Vol. 61 (7), pp. 3224-3230. Date of Electronic Publication: 2018 Mar 22.
نوع المنشور: Journal Article; Research Support, N.I.H., Extramural
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 9716531 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-4804 (Electronic) Linking ISSN: 00222623 NLM ISO Abbreviation: J Med Chem Subsets: MEDLINE
أسماء مطبوعة: Publication: Washington Dc : American Chemical Society
Original Publication: [Easton, Pa.] : American Chemical Society, [c1963-
مواضيع طبية MeSH: Amino Acids/*chemical synthesis , Amino Acids/*pharmacology , Indoles/*chemical synthesis , Indoles/*pharmacology , Mitochondria/*drug effects, Amidohydrolases/metabolism ; Animals ; Cell Line ; Energy Metabolism/drug effects ; Fatty Acids, Unsaturated/chemical synthesis ; Fatty Acids, Unsaturated/pharmacology ; Glucose/metabolism ; Homeostasis/drug effects ; Mice ; Oxygen Consumption/drug effects ; Stimulation, Chemical ; Structure-Activity Relationship
مستخلص: N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
References: J Biol Chem. 1998 Feb 13;273(7):3937-42. (PMID: 9461579)
J Agric Food Chem. 2017 Feb 8;65(5):1051-1057. (PMID: 28102080)
J Lipid Res. 2010 Jan;51(1):112-9. (PMID: 19584404)
Front Cell Neurosci. 2014 Aug 01;8:195. (PMID: 25136293)
Proc Natl Acad Sci U S A. 2010 Oct 12;107(41):17710-5. (PMID: 20876113)
J Biol Chem. 2014 Jul 11;289(28):19341-50. (PMID: 24872412)
J Biol Chem. 2001 Nov 16;276(46):42639-44. (PMID: 11518719)
Science. 1992 Dec 18;258(5090):1946-9. (PMID: 1470919)
J Biol Chem. 2008 Jul 25;283(30):21054-64. (PMID: 18499677)
Cell. 2016 Jul 14;166(2):424-435. (PMID: 27374330)
Br J Pharmacol. 2010 Aug;160(8):1857-71. (PMID: 20649585)
معلومات مُعتمدة: R00 DK105203 United States DK NIDDK NIH HHS; R01 DK124265 United States DK NIDDK NIH HHS; R00 DK111916 United States DK NIDDK NIH HHS; K99 DK111916 United States DK NIDDK NIH HHS; R37 DK031405 United States DK NIDDK NIH HHS; F31 GM126842 United States GM NIGMS NIH HHS; R01 DK031405 United States DK NIDDK NIH HHS; K99 DK105203 United States DK NIDDK NIH HHS
المشرفين على المادة: 0 (Amino Acids)
0 (Fatty Acids, Unsaturated)
0 (Indoles)
EC 3.5.- (Amidohydrolases)
EC 3.5.- (PM20D1 protein, mouse)
IY9XDZ35W2 (Glucose)
تواريخ الأحداث: Date Created: 20180314 Date Completed: 20190417 Latest Revision: 20240610
رمز التحديث: 20240610
مُعرف محوري في PubMed: PMC6335027
DOI: 10.1021/acs.jmedchem.8b00029
PMID: 29533650
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-4804
DOI:10.1021/acs.jmedchem.8b00029