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Binding and Action of Triphenylphosphonium Analog of Chloramphenicol upon the Bacterial Ribosome.

التفاصيل البيبلوغرافية
العنوان: Binding and Action of Triphenylphosphonium Analog of Chloramphenicol upon the Bacterial Ribosome.
المؤلفون: Chen CW; Department of Biological Sciences, University of Illinois at Chicago, Chicago, IL 60607, USA., Pavlova JA; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Lukianov DA; Center of Life Sciences, Skolkovo Institute of Science and Technology, 143028 Skolkovo, Russia., Tereshchenkov AG; A.N. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, 119991 Moscow, Russia., Makarov GI; Laboratory of Multiscale Modeling of Multicomponent Materials, South Ural State University, 454080 Chelyabinsk, Russia., Khairullina ZZ; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Tashlitsky VN; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Paleskava A; Petersburg Nuclear Physics Institute, National Research Center (NRC) 'Kurchatov Institute', 188300 Gatchina, Russia.; Peter the Great St.Petersburg Polytechnic University, 195251 Saint Petersburg, Russia., Konevega AL; Petersburg Nuclear Physics Institute, National Research Center (NRC) 'Kurchatov Institute', 188300 Gatchina, Russia.; Peter the Great St.Petersburg Polytechnic University, 195251 Saint Petersburg, Russia.; National Research Center (NRC) 'Kurchatov Institute', 123182 Moscow, Russia., Bogdanov AA; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.; A.N. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, 119991 Moscow, Russia., Osterman IA; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.; Center of Life Sciences, Skolkovo Institute of Science and Technology, 143028 Skolkovo, Russia., Sumbatyan NV; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.; A.N. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, 119991 Moscow, Russia., Polikanov YS; Department of Biological Sciences, University of Illinois at Chicago, Chicago, IL 60607, USA.; Department of Pharmaceutical Sciences, University of Illinois at Chicago, Chicago, IL 60607, USA.; Center for Biomolecular Sciences, University of Illinois at Chicago, Chicago, IL 60607, USA.
المصدر: Antibiotics (Basel, Switzerland) [Antibiotics (Basel)] 2021 Apr 05; Vol. 10 (4). Date of Electronic Publication: 2021 Apr 05.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI AG Country of Publication: Switzerland NLM ID: 101637404 Publication Model: Electronic Cited Medium: Print ISSN: 2079-6382 (Print) Linking ISSN: 20796382 NLM ISO Abbreviation: Antibiotics (Basel) Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI AG, 2012-
مستخلص: Chloramphenicol (CHL) is a ribosome-targeting antibiotic that binds to the peptidyl transferase center (PTC) of the bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving the properties of this inhibitor, we explored ribosome binding and inhibitory properties of a semi-synthetic triphenylphosphonium analog of CHL-CAM-C4-TPP. Our data demonstrate that this compound exhibits a ~5-fold stronger affinity for the bacterial ribosome and higher potency as an in vitro protein synthesis inhibitor compared to CHL. The X-ray crystal structure of the Thermus thermophilus 70S ribosome in complex with CAM-C4-TPP reveals that, while its amphenicol moiety binds at the PTC in a fashion identical to CHL, the C4-TPP tail adopts an extended propeller-like conformation within the ribosome exit tunnel where it establishes multiple hydrophobic Van der Waals interactions with the rRNA. The synthesized compound represents a promising chemical scaffold for further development by medicinal chemists because it simultaneously targets the two key functional centers of the bacterial ribosome-PTC and peptide exit tunnel.
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معلومات مُعتمدة: R01 GM132302 United States GM NIGMS NIH HHS; S10 OD021527 United States OD NIH HHS; R01-GM132302 United States NH NIH HHS; P30 GM124165 United States GM NIGMS NIH HHS
فهرسة مساهمة: Keywords: 70S ribosome; X-ray structure; antibiotic; binding affinity; chloramphenicol; nascent peptide exit tunnel; peptidyl transferase center; translation inhibitor
تواريخ الأحداث: Date Created: 20210430 Latest Revision: 20240504
رمز التحديث: 20240504
مُعرف محوري في PubMed: PMC8066774
DOI: 10.3390/antibiotics10040390
PMID: 33916420
قاعدة البيانات: MEDLINE
الوصف
تدمد:2079-6382
DOI:10.3390/antibiotics10040390