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Structurally Diverse Histone Deacetylase Photoreactive Probes: Design, Synthesis, and Photolabeling Studies in Live Cells and Tissue.

التفاصيل البيبلوغرافية
العنوان: Structurally Diverse Histone Deacetylase Photoreactive Probes: Design, Synthesis, and Photolabeling Studies in Live Cells and Tissue.
المؤلفون: Aboukhatwa SM; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL, 60612, USA.; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt., Hanigan TW; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL, 60612, USA., Taha TY; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL, 60612, USA., Neerasa J; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL, 60612, USA., Ranjan R; Section of Hematology/Oncology, College of Medicine, University of Illinois at Chicago, Chicago, IL, 60612, USA., El-Bastawissy EE; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt., Elkersh MA; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt.; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Pharos University, Alexandria, 21311, Egypt., El-Moselhy TF; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt., Frasor J; Department of Physiology and Biophysics, College of Medicine, University of Illinois at Chicago, Chicago, IL, 60612, USA., Mahmud N; Section of Hematology/Oncology, College of Medicine, University of Illinois at Chicago, Chicago, IL, 60612, USA., McLachlan A; Department of Microbiology and Immunology, College of Medicine, University of Illinois at Chicago, Chicago, IL, 60612, USA., Petukhov PA; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL, 60612, USA.
المصدر: ChemMedChem [ChemMedChem] 2019 Jun 05; Vol. 14 (11), pp. 1096-1107. Date of Electronic Publication: 2019 Apr 10.
نوع المنشور: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101259013 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1860-7187 (Electronic) Linking ISSN: 18607179 NLM ISO Abbreviation: ChemMedChem Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Weinheim, Germany : Wiley-VCH, c2006-
مواضيع طبية MeSH: Drug Design* , Optical Imaging*, Fluorescent Dyes/*pharmacology , Histone Deacetylase Inhibitors/*pharmacology , Histone Deacetylases/*metabolism , Photoaffinity Labels/*pharmacology, Animals ; Cells, Cultured ; Fluorescent Dyes/chemical synthesis ; Fluorescent Dyes/chemistry ; Histone Deacetylase Inhibitors/chemical synthesis ; Histone Deacetylase Inhibitors/chemistry ; Humans ; Isoenzymes/antagonists & inhibitors ; Isoenzymes/metabolism ; Liver/diagnostic imaging ; Mice ; Mice, 129 Strain ; Photoaffinity Labels/chemical synthesis ; Photoaffinity Labels/chemistry
مستخلص: Histone deacetylase (HDAC) activity is modulated in vivo by post-translational modifications and formation of multiprotein complexes. Novel chemical tools to study how these factors affect engagement of HDAC isoforms by HDAC inhibitors (HDACi) in cells and tissues are needed. In this study, a synthetic strategy to access chemically diverse photoreactive probes (PRPs) was developed and used to prepare seven novel HDAC PRPs 9-15. The class I HDAC isoform engagement by PRPs was determined in biochemical assays and photolabeling experiments in live SET-2, HepG2, HuH7, and HEK293T cell lines and in mouse liver tissue. Unlike the HDAC protein abundance and biochemical activity against recombinant HDACs, the chemotype of the PRPs and the type of cells were key in defining the engagement of HDAC isoforms in live cells. Our findings suggest that engagement of HDAC isoforms by HDACi in vivo may be substantially modulated in a cell- and tissue-type-dependent manner.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
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معلومات مُعتمدة: R21 CA183627 United States CA NCI NIH HHS; R01 CA238328 United States CA NCI NIH HHS; R01 AI125401 United States AI NIAID NIH HHS; R01 CA131970 United States CA NCI NIH HHS; R01 HL130760 United States HL NHLBI NIH HHS
فهرسة مساهمة: Keywords: histone deacetylase; inhibitors; photoaffinity labeling; target engagement; tissue labeling
المشرفين على المادة: 0 (Fluorescent Dyes)
0 (Histone Deacetylase Inhibitors)
0 (Isoenzymes)
0 (Photoaffinity Labels)
EC 3.5.1.98 (Histone Deacetylases)
تواريخ الأحداث: Date Created: 20190329 Date Completed: 20200323 Latest Revision: 20240717
رمز التحديث: 20240717
مُعرف محوري في PubMed: PMC6548601
DOI: 10.1002/cmdc.201900114
PMID: 30921497
قاعدة البيانات: MEDLINE
الوصف
تدمد:1860-7187
DOI:10.1002/cmdc.201900114