دورية أكاديمية
أعرض في EDS

Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.

التفاصيل البيبلوغرافية
العنوان: Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.
المؤلفون: Li J; Department of Chemistry, Texas A&M University, PO Box 30012, College Station, Texas 77842-3012, USA., Cisar JS, Zhou CY, Vera B, Williams H, Rodríguez AD, Cravatt BF, Romo D
المصدر: Nature chemistry [Nat Chem] 2013 Jun; Vol. 5 (6), pp. 510-7. Date of Electronic Publication: 2013 May 19.
نوع المنشور: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: Nature Pub. Group Country of Publication: England NLM ID: 101499734 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1755-4349 (Electronic) Linking ISSN: 17554330 NLM ISO Abbreviation: Nat Chem Subsets: MEDLINE
أسماء مطبوعة: Original Publication: London : Nature Pub. Group
مواضيع طبية MeSH: Alkynes/*chemistry , Antineoplastic Agents/*chemistry , Antineoplastic Agents/*pharmacology , Biological Products/*chemistry , Diterpenes/*chemistry , Diterpenes/*pharmacology, Alkenes/chemistry ; Amination ; Aziridines/chemistry ; Catalysis ; Cell Survival/drug effects ; HL-60 Cells ; Humans ; Proteomics ; Rhodium/chemistry ; Structure-Activity Relationship
مستخلص: Natural products have a venerable history of, and enduring potential for the discovery of useful biological activity. To fully exploit this, the development of chemical methodology that can functionalize unique sites within these complex structures is highly desirable. Here, we describe the use of rhodium(II)-catalysed C-H amination reactions developed by Du Bois to carry out simultaneous structure-activity relationship studies and arming (alkynylation) of natural products at 'unfunctionalized' positions. Allylic and benzylic C-H bonds in the natural products undergo amination while olefins undergo aziridination, and tertiary amine-containing natural products are converted to amidines by a C-H amination-oxidation sequence or to hydrazine sulfamate zwitterions by an unusual N-amination. The alkynylated derivatives are ready for conversion into cellular probes that can be used for mechanism-of-action studies. Chemo- and site-selectivity was studied with a diverse library of natural products. For one of these-the marine-derived anticancer diterpene, eupalmerin acetate-quantitative proteome profiling led to the identification of several protein targets in HL-60 cells, suggesting a polypharmacological mode of action.
التعليقات: Erratum in: Nat Chem. 2013 Jul;5(7):634.
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معلومات مُعتمدة: CA087660 United States CA NCI NIH HHS; F32GM095245-01 United States GM NIGMS NIH HHS; F32 DA032541 United States DA NIDA NIH HHS; F32 GM095245 United States GM NIGMS NIH HHS; R01 CA087660 United States CA NCI NIH HHS; GM806307 United States GM NIGMS NIH HHS; R37 CA087660 United States CA NCI NIH HHS; R01 GM086307 United States GM NIGMS NIH HHS; SC1 GM086271 United States GM NIGMS NIH HHS; GM086271 United States GM NIGMS NIH HHS
سلسلة جزيئية: PubChem-Substance 162163319; 162163320; 162163321; 162163322; 162163323; 162163324; 162163325; 162163326; 162163327; 162163328; 162163329; 162163330; 162163331; 162163332; 162163333; 162163334; 162163335; 162163336; 162163337; 162163338; 162163339; 162163340; 162163341; 162163342; 162163343; 162163344; 162163345; 162163346; 162163347
المشرفين على المادة: 0 (Alkenes)
0 (Alkynes)
0 (Antineoplastic Agents)
0 (Aziridines)
0 (Biological Products)
0 (Diterpenes)
37299-08-4 (eupalmerin acetate)
54P5FEX9FH (aziridine)
DMK383DSAC (Rhodium)
تواريخ الأحداث: Date Created: 20130523 Date Completed: 20130716 Latest Revision: 20211021
رمز التحديث: 20240628
مُعرف محوري في PubMed: PMC4041531
DOI: 10.1038/nchem.1653
PMID: 23695633
قاعدة البيانات: MEDLINE
الوصف
تدمد:1755-4349
DOI:10.1038/nchem.1653