دورية أكاديمية
A novel acyclic oligomycin A derivative formed via retro-aldol rearrangement of oligomycin A.
| العنوان: | A novel acyclic oligomycin A derivative formed via retro-aldol rearrangement of oligomycin A. |
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| المؤلفون: | Lysenkova LN; Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russian Federation., Turchin KF, Korolev AM, Bykov EE, Danilenko VN, Bekker OB, Trenin AS, Elizarov SM, Dezhenkova LG, Shtil AA, Preobrazhenskaya MN |
| المصدر: | The Journal of antibiotics [J Antibiot (Tokyo)] 2012 Aug; Vol. 65 (8), pp. 405-11. Date of Electronic Publication: 2012 May 23. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: Nature Publishing Group Country of Publication: England NLM ID: 0151115 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1881-1469 (Electronic) Linking ISSN: 00218820 NLM ISO Abbreviation: J Antibiot (Tokyo) Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: 2009- : London : Nature Publishing Group Original Publication: Tokyo, Japan Antibiotics Research Assn. |
| مواضيع طبية MeSH: | Anti-Bacterial Agents/*chemical synthesis , Antineoplastic Agents/*chemical synthesis , Enzyme Inhibitors/*chemical synthesis , Oligomycins/*chemical synthesis, ATP Synthetase Complexes/antagonists & inhibitors ; ATP Synthetase Complexes/metabolism ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Apoptosis/physiology ; Cell Survival/drug effects ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; HCT116 Cells ; Humans ; K562 Cells ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Oligomycins/chemistry ; Oligomycins/pharmacology ; Spectrometry, Mass, Electrospray Ionization ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet |
| مستخلص: | The antibiotic oligomycin A in the presence of K(2)CO(3) and n-Bu(4)NHSO(4) in chloroform in phase-transfer conditions afforded a novel derivative through the initial retro-aldol fragmentation of the 8,9 bond, followed by further transformation of the intermediate aldehyde. NMR, MS and quantum chemical calculations showed that the novel compound is the acyclic oligomycin A derivative, in which the 8,9 carbon bond is disrupted and two polyfunctional branches are connected with spiroketal moiety in positions C-23 and C-25. The tri-O-acetyl derivative of the novel derivative was prepared. The acyclic oligomycin A derivative retained the ability to induce apoptosis in tumor cells at low micromolar concentrations, whereas its antimicrobial potencies decreased substantially. The derivative virtually lost the inhibitory activity against F(0)F(1) ATP synthase-containing proteoliposomes, strongly suggesting the existence of the target(s) beyond F(0)F(1) ATP synthase that is important for the antitumor potency of oligomycin A. |
| المشرفين على المادة: | 0 (Anti-Bacterial Agents) 0 (Antineoplastic Agents) 0 (Enzyme Inhibitors) 0 (Oligomycins) EC 2.7.4.- (ATP Synthetase Complexes) |
| تواريخ الأحداث: | Date Created: 20120524 Date Completed: 20121231 Latest Revision: 20120828 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1038/ja.2012.38 |
| PMID: | 22617550 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1881-1469 |
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| DOI: | 10.1038/ja.2012.38 |