Synthesis and characterization of pyruvate-isoniazid analogs and their copper complexes as potential ICL inhibitors

被引：32

作者：

Shingnapurkar, Dipti ^{[1
]}

Dandawate, Prasad ^{[2
]}

Anson, Christopher E. ^{[3
]}

Powell, Annie K. ^{[3
]}

Afrasiabi, Zahra ^{[4
]}

Sinn, Ekkehard ^{[4
]}

Pandit, Shital ^{[6
]}

Swamy, K. Venkateswara ^{[6
]}

Franzblau, Scott ^{[5
]}

Padhye, Subhash ^{[1
,2
]}

机构：

[1] Univ Pune, Dept Chem, Pune 411007, Maharashtra, India

[2] Univ Pune, MCE Soc Abeda Inamdar Senior Coll Arts Sci & Comm, Dept Chem, ISTRA, Pune 411001, Maharashtra, India

[3] Karlsruhe Inst Technol KIT, Inst Anorgan Chem, D-76131 Karlsruhe, Germany

[4] Univ Missouri, Dept Chem, Rolla, MO 65401 USA

[5] Univ Illinois, Inst TB Res, Dept Med Chem & Pharmacognosy, Chicago, IL 60612 USA

[6] Dr DY Patil Inst Biotechnol & Bioinformat, Pune 411044, Maharashtra, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 09期

关键词：

Pyruvic acid; Isocitrate lyase; Persistent mycobacteria; Copper complex; MYCOBACTERIUM-TUBERCULOSIS; ISOCITRATE LYASE; IN-VITRO; ANTIMYCOBACTERIAL EVALUATION; CRYSTAL-STRUCTURE; STRUCTURAL-CHARACTERIZATION; CYTOTOXICITY; PERSISTENCE; HYDRAZONE; DESIGN;

D O I：

10.1016/j.bmcl.2012.03.047

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Currently used anti-tubercular drugs target actively growing Mycobacterium tuberculosis (Mtb) but there are no current therapies targeting persistent mycobacteria. Isocitrate lyase (ICL) is an important enzyme of the glyoxylate shunt pathway used by Mtb for sustaining intracellular infection in inflammatory macrophages under conditions of stress such as nutrient depletion and anaerobic metabolism. Since the humans do not possess this enzyme it constitutes an attractive target for selective drug design. Present work describes synthesis and structural characterization of pyruvate-isoniazid conjugates and their copper complexes with potent anti-tubercular activities against M. tuberculosis H37Rv. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3172 / 3176

页数：5

共 45 条

[1]

[Anonymous], WHO REP 2011 GLOB TU

[2]

Augustynowicz-Kopec Ewa, 2002, Acta Pol Pharm, V59, P452

[3]

Augustynowicz-Kopec Ewa, 2002, Acta Pol Pharm, V59, P443

[4] Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection [J].

Banerjee, Debjani ;

Yogeeswari, Perumal ;

Bhat, Pritesh ;

Thomas, Anisha ;

Srividya, Madala ;

Sriram, Dharmarajan .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) :106-121

[5] Mycobacterial persistence: adaptation to a changing environment [J].

Bentrup, KHZ ;

Russell, DG .

TRENDS IN MICROBIOLOGY, 2001, 9 (12) :597-605

[6]

Bindu P, 1999, POLYHEDRON, V18, P321

[7] Nickel(II) 2,6-diacetylpyridine bis(isonicotinoylhydrazonate) and bis(benzoylhydrazonate) complexes:: Structure and antimycobacterial evaluation.: Part XI [J].

Bottari, B ;

Maccari, R ;

Monforte, F ;

Ottanà, R ;

Vigorita, MG ;

Bruno, G ;

Nicolò, F ;

Rotondo, A ;

Rotondo, E .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (08) :2203-2211

[8] The structure and domain organization of Escherichia coli isocitrate lyase [J].

Britton, KL ;

Abeysinghe, ISB ;

Baker, PJ ;

Barynin, V ;

Diehl, P ;

Langridge, SJ ;

McFadden, BA ;

Sedelnikova, SE ;

Stillman, TJ ;

Weeradechapon, K ;

Rice, DW .

ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, 2001, 57 :1209-1218

[9] Mixed-valence Cu(II)/Cu(I) complex of quinolone ciprofloxacin isolated by a hydrothermal reaction in the presence of L-histidine: comparison of biological activities of various copper-ciprofloxacin compounds [J].

Drevensek, P ;

Zupancic, T ;

Pihlar, B ;

Jerala, R ;

Kolitsch, U ;

Plader, A ;

Turel, I .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (02) :432-442

[10] MONOMERIC AND ANION-BRIDGED DIMERIC AND POLYMERIC OXAMIDE OXIME COMPLEXES OF COPPER(II) - PREPARATION, CRYSTAL AND MOLECULAR-STRUCTURES, AND MAGNETIC-PROPERTIES [J].

ENDRES, H ;

NOTHE, D ;

ROSSATO, E ;

HATFIELD, WE .

INORGANIC CHEMISTRY, 1984, 23 (22) :3467-3473

← 1 2 3 4 5 →