Design, Synthesis, and Evaluation of Thiol-Activated Sources of Sulfur Dioxide (SO2) as Antimycobacterial Agents

被引:163
作者
Malwal, Satish R. [1 ]
Sriram, Dharmarajan [2 ]
Yogeeswari, Perumal [2 ]
Konkimalla, V. Badireenath [3 ]
Chakrapani, Harinath [1 ]
机构
[1] Indian Inst Sci Educ & Res, Dept Chem, Pune 411008, Maharashtra, India
[2] Birla Inst Technol & Sci Pilani, Dept Pharm, Hyderabad 500078, Andhra Pradesh, India
[3] NISER, Sch Biol Sci, Bhubaneswar 751005, Orissa, India
关键词
NITRIC-OXIDE; MYCOBACTERIUM-TUBERCULOSIS; THERAPEUTIC AGENTS; MEAT-PRODUCTS; !text type='JS']JS[!/text]-K; SULFITE; FRESH; INHALATION; MECHANISM; SYSTEM;
D O I
10.1021/jm201023g
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Here, 2,4-dinitrophenylsulfonamides with tunable cysteine-activated SO2 release profiles with half-lives of SO2 release varying from 2 to 63 min are reported. N-Benzyl-2,4-dinitrobenzenesulfonamide (6), which is prepared in one step from commercial sources, had a potency (MIC = 0.15 mu M) of inhibiting Mycobacterium tuberculosis (Mtb) higher than the clinical agent isoniazid (MIC = 0.37 mu M).
引用
收藏
页码:553 / 557
页数:5
相关论文
共 42 条
[1]  
Amerine M.A., 1980, The Technology of Wine Making, V4th
[2]   RESIDUAL LEVELS OF FREE AND TOTAL SULFITE IN FRESH AND COOKED BURGERS [J].
ARMENTIAALVAREZ, A ;
FERNANDEZCASERO, A ;
GARCIAMORENO, C ;
PENAEGIDO, MJ .
FOOD ADDITIVES AND CONTAMINANTS, 1993, 10 (02) :157-165
[3]   COMPARISON OF METHODS FOR THE DETERMINATION OF FREE AND BOUND SULFUR-DIOXIDE IN STORED BRITISH FRESH SAUSAGE [J].
BANKS, JG ;
BOARD, RG .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1982, 33 (02) :197-203
[4]   Therapeutic potential of nitric oxide in cancer [J].
Bonavida, Benjamin ;
Khineche, Soraya ;
Huerta-Yepez, Sara ;
Garban, Hermes .
DRUG RESISTANCE UPDATES, 2006, 9 (03) :157-173
[5]  
Braude E.A., 2013, Determination of Organic Structures by Physical Methods
[6]   Fluorescent and colorimetric probes for detection of thiols [J].
Chen, Xiaoqiang ;
Zhou, Ying ;
Peng, Xiaojun ;
Yoon, Juyoung .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2120-2135
[7]   Antimicrobial reactive oxygen and nitrogen species: Concepts and controversies [J].
Fang, FC .
NATURE REVIEWS MICROBIOLOGY, 2004, 2 (10) :820-832
[8]   Reductive Stress in Microbes: Implications for Understanding Mycobacterium tuberculosis Disease and Persistence [J].
Farhana, Aisha ;
Guidry, Loni ;
Srivastava, Anup ;
Singh, Amit ;
Hondalus, Mary K. ;
Steyn, Adrie J. C. .
ADVANCES IN MICROBIAL PHYSIOLOGY, VOL 57, 2010, 57 :43-117
[9]   Multidrug-resistant and extensively drug-resistant tuberculosis: The National Institute of Allergy and Infectious Diseases research agenda and recommendations for priority research [J].
Fauci, Anthony S. .
JOURNAL OF INFECTIOUS DISEASES, 2008, 197 (11) :1493-1498
[10]   A REVIEW OF SULFITES IN FOODS - ANALYTICAL METHODOLOGY AND REPORTED FINDINGS [J].
FAZIO, T ;
WARNER, CR .
FOOD ADDITIVES AND CONTAMINANTS PART A-CHEMISTRY ANALYSIS CONTROL EXPOSURE & RISK ASSESSMENT, 1990, 7 (04) :433-454