Literature DB >> 30461269

Semisynthesis of Platensimycin Derivatives with Antibiotic Activities in Mice via Suzuki-Miyaura Cross-Coupling Reactions.

Youchao Deng1, Meng Su1, Dingding Kang1, Xingyun Liu1, Zhongqing Wen1, Yuling Li1, Lin Qiu1, Ben Shen, Yanwen Duan1,2,3, Yong Huang1,3.   

Abstract

Platensimycin (PTM), originally isolated from soil bacteria Streptomyces platensis, is a potent FabF inhibitor against many Gram-positive pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci. However, the further clinical development of PTM is hampered by its poor pharmacokinetic properties. In this study, 20 PTM derivatives were prepared by Suzuki-Miyaura cross-coupling reactions catalyzed by Pd (0)/C. Compared to PTM, 6-pyrenyl PTM (6t) showed improved antibacterial activity against MRSA in a mouse peritonitis model. Our results support the strategy to target the essential fatty acid synthases in major pathogens, in order to discover and develop new generations of antibiotics.

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Year:  2018        PMID： 30461269      PMCID： PMC7110910          DOI： 10.1021/acs.jmedchem.8b01580

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  27 in total

1.  Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C.

Authors:  François-Xavier Felpin
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

2.  Dialkylamino-2,4-dihydroxybenzoic acids as easily synthesized analogues of platensimycin and platencin with comparable antibacterial properties.

Authors:  Jingxin Wang; Herman O Sintim
Journal:  Chemistry       Date:  2011-02-14       Impact factor: 5.236

3.  Pharmacodynamics of glycopeptides in the mouse peritonitis model of Streptococcus pneumoniae or Staphylococcus aureus infection.

Authors:  J D Knudsen; K Fuursted; S Raber; F Espersen; N Frimodt-Moller
Journal:  Antimicrob Agents Chemother       Date:  2000-05       Impact factor: 5.191

4.  A Facile Semi-Synthetic Approach towards Halogen-Substituted Aminobenzoic Acid Analogues of Platensimycin.

Authors:  Lin Qiu; Kai Tian; Jian Pan; Lin Jiang; Hu Yang; Xiangcheng Zhu; Ben Shen; Yanwen Duan; Yong Huang
Journal:  Tetrahedron       Date:  2016-12-28       Impact factor: 2.457

Review 5.  Platensimycin and platencin: Inspirations for chemistry, biology, enzymology, and medicine.

Authors:  Jeffrey D Rudolf; Liao-Bin Dong; Ben Shen
Journal:  Biochem Pharmacol       Date:  2016-11-16       Impact factor: 5.858

6.  Pharmacological properties of the marine natural product marinopyrrole A against methicillin-resistant Staphylococcus aureus.

Authors:  Nina M Haste; Chambers C Hughes; Dan N Tran; William Fenical; Paul R Jensen; Victor Nizet; Mary E Hensler
Journal:  Antimicrob Agents Chemother       Date:  2011-04-18       Impact factor: 5.191

Review 7.  Bacterial fatty acid metabolism in modern antibiotic discovery.

Authors:  Jiangwei Yao; Charles O Rock
Journal:  Biochim Biophys Acta Mol Cell Biol Lipids       Date:  2016-09-23       Impact factor: 4.698

8.  Total synthesis and antibacterial properties of carbaplatensimycin.

Authors:  K C Nicolaou; Yefeng Tang; Jianhua Wang; Antonia F Stepan; Ang Li; Ana Montero
Journal:  J Am Chem Soc       Date:  2007-11-08       Impact factor: 15.419

9.  Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances.

Authors:  Irith Wiegand; Kai Hilpert; Robert E W Hancock
Journal:  Nat Protoc       Date:  2008       Impact factor: 13.491

10.  The semi-synthesis, biological evaluation and docking analysis of the oxime, hydrazine and hydrazide derivatives of platensimycin.

Authors:  Youchao Deng; Dingding Kang; Jie Shi; Wenqing Zhou; Aijun Sun; Jianhua Ju; Xiangcheng Zhu; Ben Shen; Yanwen Duan; Yong Huang
Journal:  Medchemcomm       Date:  2018-03-06       Impact factor: 3.597
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  5 in total

1.  Late-Stage Functionalization of Platensimycin Leading to Multiple Analogues with Improved Antibacterial Activity in Vitro and in Vivo.

Authors:  Youchao Deng; Xiang Weng; Yuling Li; Meng Su; Zhongqing Wen; Xinxin Ji; Nan Ren; Ben Shen; Yanwen Duan; Yong Huang
Journal:  J Med Chem       Date:  2019-07-02       Impact factor: 7.446

2.  Evaluation of Platensimycin and Platensimycin-Inspired Thioether Analogues against Methicillin-Resistant Staphylococcus aureus in Topical and Systemic Infection Mouse Models.

Authors:  Meng Su; Lin Qiu; Youchao Deng; Claudia H Ruiz; Jeffrey D Rudolf; Liao-Bin Dong; Xueqiong Feng; Michael D Cameron; Ben Shen; Yanwen Duan; Yong Huang
Journal:  Mol Pharm       Date:  2019-06-19       Impact factor: 4.939

3.  Morphing Natural Product Platensimycin via Heck, Sonogashira, and One-Pot Sonogashira/Cycloaddition Reactions to Produce Antibiotics with In Vivo Activity.

Authors:  Youchao Deng; Yuling Li; Zhongqing Wen; Claudia H Ruiz; Xiang Weng; Michael D Cameron; Yanwen Duan; Yong Huang
Journal:  Antibiotics (Basel)       Date:  2022-03-23

4.  Semisynthesis and Biological Evaluation of Platencin Thioether Derivatives: Dual FabF and FabH Inhibitors against MRSA.

Authors:  Yuling Li; Xiang Weng; Youchao Deng; Jian Pan; Saibin Zhu; Zhongqing Wen; Yanqiu Yuan; Shaowen Li; Ben Shen; Yanwen Duan; Yong Huang
Journal:  ACS Med Chem Lett       Date:  2021-02-15       Impact factor: 4.345

Review 5.  Therapeutic peptides: current applications and future directions.

Authors:  Lei Wang; Nanxi Wang; Wenping Zhang; Xurui Cheng; Zhibin Yan; Gang Shao; Xi Wang; Rui Wang; Caiyun Fu
Journal:  Signal Transduct Target Ther       Date:  2022-02-14
  5 in total

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