Solvent-driven structural topology involving energetically significant intra- and intermolecular chelate ring contacts and anticancer activities of Cu(ii) phenanthroline complexes involving benzoates: experimental and theoretical studies. Issue 29 (24th May 2019)

• Record Type: Journal Article
• Authors: Bhattacharyya, Manjit K.; Saha, Utpal; Dutta, Debajit; Das, Amal; Verma, Akalesh K.; Frontera, Antonio
• Is Part Of: RSC advances. Volume 9:Issue 29(2019)
• Page Start: 16339
• Page End: 16356
• Publication Date: 2019-05-24
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9ra01181a
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Solvent driven structural topology and in vitro anticancer evaluation of two new Cu(ii ) complexes considering cytotoxicity, apoptosis and molecular docking. Abstract : Two new coordination solids [Cu2 (μ 2 -Bz)4 (CH3 OH)2 ][Cu2 (η 2 -Bz)2 (phen)2 (H2 O)2 ]·(NO3 )2 (1 ) and [Cu(phen)(H2 O)(Bz)(η 2 -Bz)] (2 ) (phen = 1, 10-phenanthroline; Bz = benzoate) have been synthesized and characterized using elemental analysis, TGA, spectroscopic (IR, UV-vis-NIR and ESR) and single crystal X-ray diffraction techniques. Change of the solvent from methanol to DMF results in changes in the architectures that are triggered by a change from square pyramidal to octahedral coordination at the divalent metal centers for complexes1 and2 respectively. The structural topology of the complexes is established by the interplay of strong O–H⋯O and weak C–H⋯O, C–H⋯C, π–π stacking interactions. Unconventional parallel intramolecular and anti-parallel intermolecular contacts involving the chelate rings (CR) also stabilize the structures. The energetic analyses of the structures evidence that the parallel arrangement is energetically favoured which is likely due to the presence of the Cu⋯Cu cuprophilic interaction in1 that is not established in2 . Compound1 exhibits the highest antibacterial activity against Rhizobium leguminosarum among the tested cultures. In vitro cytotoxicity and apoptosis studies were carried out for compounds1 and2 on malignant Dalton's lymphoma cell line (DL). Both compounds showed a significant effect on the decrease in cell viability as compared to a control, while compound2 induced remarkable cytotoxicity towards DL cells. Treatment also showed the appearance of membrane blebbing, chromatin condensation and fragmented nuclei which are typical characteristic features of apoptotic cell death. Furthermore, a docking study revealed that both compounds docked in the active sites of all the cancer target proteins under study. Moreover, SAR analysis revealed that oxygen and nitrogen atoms of compound1 and the oxygen atoms of compound2 are crucial for biological activities.