Ru(II)-based antineoplastic: A "wingtip" N-heterocyclic carbene facilitates access to a new class of organometallics that are cytotoxic to common cancer cell lines

被引:17
作者
Mondal, Ambarish [1 ]
Tripathy, Rajat K. [1 ]
Dutta, Parul [2 ]
Santra, Manas Kumar [2 ]
Isab, Anvarhusein A. [3 ]
Bielawski, Christopher W. [4 ,5 ,6 ]
Kisan, Hemanta K. [1 ]
Chandra, Swapan K. [7 ]
Dinda, Joydev [1 ]
机构
[1] Utkal Univ, Dept Chem, Bhubaneswar 751004, Odisha, India
[2] Natl Ctr Cell Sci, Pune 411007, Maharashtra, India
[3] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia
[4] IBS, CMCM, Ulsan 44919, South Korea
[5] UNIST, Dept Chem, Ulsan 44919, South Korea
[6] UNIST, Dept Energy Engn, Ulsan 44919, South Korea
[7] Visva Bharati Univ, Dept Chem, Santini Ketan 731235, W Bengal, India
基金
新加坡国家研究基金会;
关键词
cytotoxicity; Gold(I)-NHC; N-heterocyclic carbene; silver(I)-NHC; GOLD(III) COMPLEXES; RUTHENIUM COMPLEXES; NATURAL-PRODUCTS; ANTICANCER; AG(I); NHC; INHIBITORS; APOPTOSIS; SILVER(I); AGENTS;
D O I
10.1002/aoc.4692
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The syntheses, structures, and chemotherapeutic activities of Ag(I)-, Au(I)-, and Ru(II)-complexes ligated to a novel N-heterocyclic carbene ligand, 2-(4-nitrophenyl)imidazo[1,5-a]pyridin-2-ylidene (1), are described. The corresponding complexes, [Ag(1)(2)][PF6], [Au(1)(2)][PF6] (3), and [Ru(1)(p-cymene)Cl][PF6] (4), were prepared using convenient transmetallation chemistry and characterized using a range of spectroscopic and analytical techniques. X-ray crystallography revealed that complexes 2 and 3 adopted linear structures whereas 4 exhibited a prototypical "piano-stool"-like geometry; the structural assignments were further supported by DFT calculations. A series of in vitro studies revealed that while the aforementioned Ag(I), Au(I) and Ru(II) complexes exhibited significant cytotoxicities against the human colon adenocarcinoma (HCT 116), lung cancer (A549), and breast cancer (MCF7) cell lines, the Ru derivative was most prominent.
引用
收藏
页数:14
相关论文
共 88 条
[1]   New aromatic nitro compounds from Salegentibacter sp T436, an Arctic Sea ice bacterium:: Taxonomy, fermentation, isolation and biological activities [J].
Al-Zereini, Wael ;
Schuhmann, Imelda ;
Laatsch, Hartmut ;
Helmke, Elisabeth ;
Anke, Heidrun .
JOURNAL OF ANTIBIOTICS, 2007, 60 (05) :301-308
[2]  
[Anonymous], 2005, PHARM CHEM J+, DOI DOI 10.1007/S11094-006-0023-9
[3]   Ruthenium-based chemotherapeutics: are they ready for prime time? [J].
Antonarakis, Emmanuel S. ;
Emadi, Ashkan .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 2010, 66 (01) :1-9
[4]   A Square-Planar Ruthenium(II) Complex with a Low-Spin Configuration [J].
Askevold, Bjorn ;
Khusniyarov, Marat M. ;
Herdtweck, Eberhardt ;
Meyer, Karsten ;
Schneider, Sven .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (41) :7566-7569
[5]   BENZIMIDAZOLE CONDENSED RING-SYSTEM .9. POTENTIAL ANTINEOPLASTICS - NEW SYNTHESIS OF SOME PYRIDO[1,2-A]BENZIMIDAZOLES AND RELATED DERIVATIVES [J].
BADAWEY, E ;
KAPPE, T .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (04) :327-332
[6]   Synthesis of imidazo[1,2-a]pyridines: a decade update [J].
Bagdi, Avik Kumar ;
Santra, Sougata ;
Monir, Kamarul ;
Hajra, Alakananda .
CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575
[7]   Targeting the mitochondrial cell death pathway with gold compounds [J].
Barnard, Peter J. ;
Berners-Price, Susan J. .
COORDINATION CHEMISTRY REVIEWS, 2007, 251 (13-14) :1889-1902
[8]   Approaching tumour therapy beyond platinum drugs Status of the art and perspectives of ruthenium drug candidates [J].
Bergamo, A. ;
Gaiddon, C. ;
Schellens, J. H. M. ;
Beijnen, J. H. ;
Sava, G. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2012, 106 (01) :90-99
[9]   Ruthenium anticancer compounds: myths and realities of the emerging metal-based drugs [J].
Bergamo, Alberta ;
Sava, Gianni .
DALTON TRANSACTIONS, 2011, 40 (31) :7817-7823
[10]   Caffeine-Based Gold(I) N-Heterocyclic Carbenes as Possible Anticancer Agents: Synthesis and Biological Properties [J].
Bertrand, Benoit ;
Stefan, Loic ;
Pirrotta, Marc ;
Monchaud, David ;
Bodio, Ewen ;
Richard, Philippe ;
Le Gendre, Pierre ;
Warmerdam, Elena ;
de Jager, Marina H. ;
Groothuis, Geny M. M. ;
Picquet, Michel ;
Casini, Angela .
INORGANIC CHEMISTRY, 2014, 53 (04) :2296-2303