Silver Complexes of N-Heterocyclic Carbenes as Anticancer Agents: A Review
Life Sciences-Medicinal Chemistry
DOI:
https://doi.org/10.22376/ijpbs/lpr.2022.12.5.L123-129Keywords:
Silver Metal Complexes, N-Heterocyclic Carbenes, Antimicrobial Agents, Anticancer AgentsAbstract
This review covers the explanation of all the biological efficiencies of the N-Heterocyclic Carbenes (NHCs). Most of the reviews of NHCs focused on its chemical and physical applications, we have noted the properties, types and applications of metal complexes of NHCS. Our principle aim is to throw a light on the biological applications of the complexes. N heterocyclic carbenes (NHC) have been discovered in the 90's and have been marking an important place in organic chemistry. NHCs contain divalent carbon atoms. It is bound to at least one nitrogen atom. Presence of heteroatoms imparts them a wide range of electronic behavior. They create stable bonds and compounds making them excellent ligands in coordination chemistry. Silver metal complexes of organic ligands had been an interesting research area for the pharmaceutical researchers. Because of the electron donating ability of NHCs, the formation of Ag metal complexes had been pursued by many inorganic chemists and they were evaluated for various biological activities. Thus, in this review we have listed out the Ag-NHCs which have anticancer potential and its use as cytotoxic therapeutic agents. This article concludes with the basic concept that, how to design efficient Ag-NHCs in order to develop efficient, biologically active metal complex derivatives.
References
Arduengo AJ, Harlow RL, Kline MA. A stable crystalline carbene. J Am Chem Soc. 1991a;113(1):361-3. doi: 10.1021/ja00001a054.
Bertrand B, Stefan L, Pirrotta M, Monchaud D, Bodio E, Richard P et al. Caffeine-based gold(I) N-heterocyclic carbenes as possible anticancer agents: synthesis and biological properties. Inorg Chem. 2014;53(4):2296-303. doi: 10.1021/ic403011h, PMID 24499428.
Arduengo AJ, Dias HVR, Harlow RL, Kline M. Electronic stabilization of nucleophilic carbenes. J Am Chem Soc. 1992;114(14):5530-4. doi: 10.1021/ja00040a007.
Patil SA, Patil SA, Patil R, Keri RS, Budagumpi S, Balakrishna GR et al. N-heterocyclic carbene metal complexes as bio-organometallic antimicrobial and anticancer drugs. Future Med Chem. 2015;7(10):1305-33. doi: 10.4155/fmc.15.61, PMID 26144266.
Arduengo AJ, Dias HVR, Dixon DA, Harlow RL, Klooster WT, Koetzle TF. Electron distribution in a stable carbene. J Am Chem Soc. 1994;116(15):6812-22. doi: 10.1021/ja00094a040.
Samantaray MK, Katiyar V, Roy D, Pang K, Nanavati H, Stephen R et al. A cationic (N-heterocyclic carbene) silver complex as catalyst for bulk ring-opening polymerization of L-lactides. Eur J Inorg Chem. 2006;2006(15):2975-84. doi: 10.1002/ejic.200600209.
Samantaray MK, Roy D, Patra A, Stephen R, Saikh M, Sunoj RB et al. Experimental and theoretical studies of a silver complex of O-functionalized N- heterocyclic carbene. J Organomet Chem. 2006b;691(18):3797-805. doi: 10.1016/j.jorganchem.2006.05.037.
Lee M, Hu CH. Density functional study of N-heterocyclic and diaminocarbene complexes: comparison with phosphines. Organometallics. 2004;23(5):976-83. doi: 10.1021/om0341451.
Hayes JM, Viciano M, Peris E, Ujaque G, Lledós A. Mechanism of formation of silver N-heterocyclic carbenes using silver oxide: a theoretical study. Organometallics. 2007;26(25):6170-83. doi: 10.1021/om700898d.
Budagumpi S, Haque RA, Endud S, Rehman GU, Salman AW. Biologically relevant silver(I)-N-heterocyclic carbene complexes: synthesis, structure, intramolecular interactions, and applications. Eur J Inorg Chem. 2013;2013(25):4367-88. doi: 10.1002/ejic.201300483.
Zetty Zulikha H, Haque RA, Budagumpi S, Abdul Majid AMS. Topology control in nitrile-functionalized silver(I)–N-heterocyclic carbene complexes: Synthesis, molecular structures, and in vitro anticancer studies. Inorganica Chimica Acta. 2014;411:40-7. doi: 10.1016/j.ica.2013.11.011.
Iqbal MA, Haque RA, Ahamed MBK, Majid AMSA, Al-Rawi SS. Synthesis and anticancer activity of para-xylyl linked bis-benzimidazolium salts and respective Ag(I) N-heterocyclic carbene complexes. Med Chem Res. 2013;22(5):2455-66. doi: 10.1007/S00044-012-0240-6.
Li Y, Liu GF, Tan CP, Ji LN, Mao ZW. Antitumor properties and mechanisms of mitochondria-targeted Ag(I) and Au(I) complexes containing N- heterocyclic carbenes derived from cyclophanes. Metallomics. 2014;6(8):1460-8. doi: 10.1039/c4mt00046c, PMID 24788133.
Eloy L, Jarrousse AS, Teyssot ML, Gautier A, Morel L, Jolivalt C et al. Anticancer activity of silver-N-heterocyclic carbene complexes: caspase-independent induction of apoptosis via mitochondrial apoptosis-inducing factor (AIF). ChemMedChem. 2012;7(5):805-14. doi: 10.1002/cmdc.201200055, PMID 22383263.
Siciliano TJ, Deblock MC, Hindi KM, Durmus S, Panzner MJ, Tessier CA et al. Synthesis and anticancer properties of gold(I) and silver(I) N- heterocyclic carbene complexes. J Organomet Chem. 2011;696(5):1066-71. doi: 10.1016/j.jorganchem.2010.10.054.
Medvetz DA, Hindi KM, Panzner MJ, Ditto AJ, Yun YH, Youngs WJ. Anticancer activity of Ag(I) N-heterocyclic carbene complexes derived from 4,5-dichloro-1H-imidazole. Met Based Drugs. 2008;2008:384010. doi: 10.1155/2008/384010, PMID 18615197.
Patil S, Deally A, Gleeson B, Müller-Bunz HM, Paradisi F, Tacke M. Novel benzyl-substituted N-heterocyclic carbene–silver acetate complexes: synthesis, cytotoxicity and antibacterial studies. Metallomics. 2011;3(1):74-88. doi: 10.1039/c0mt00034e, PMID 21135954.
Liu C, Liu Z, Li M, Li X, Wong YS, Ngai SM et al. Enhancement of auranofin-induced apoptosis in mcf-7 human breast cells by selenocystine, a synergistic inhibitor of thioredoxin reductase. PLOS ONE. 2013;8(1):e53945. doi: 10.1371/journal.pone.0053945, PMID 23342042.
Iqbal MA, Umar MI, Haque RA, Khadeer Ahamed MBK, Asmawi MZ, Majid AMSA. Macrophage and colon tumor cells as targets for a binuclear silver(I) N-heterocyclic carbene complex, an anti-inflammatory and apoptosis mediator. J Inorg Biochem. 2015;146:1-13. doi: 10.1016/j.jinorgbio.2015.02.001, PMID 25699476.
Haque RA, Salman AW, Budagumpi S, Abdullah AA, Majid AMSA. Sterically tuned Ag(I)- and Pd(II)-N-heterocyclic carbene complexes of imidazol-2-ylidenes: synthesis, crystal structures, and in vitro antibacterial and anticancer studies. Metallomics. 2013;5(6):760-9. doi: 10.1039/c3mt00051f, PMID 23645390.
Gandin V, Pellei M, Marinelli M, Marzano C, Dolmella A, Giorgetti M et al. Synthesis and in vitro antitumor activity of water soluble sulfonate- and ester-functionalized silver(I) N-heterocyclic carbene complexes. J Inorg Biochem. 2013;129:135-44. doi: 10.1016/j.jinorgbio.2013.09.011, PMID 24121303.
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