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Synthesis, characterisation, nuclease and cytotoxic activity of phosphate-free and phosphate-containing copper \(4^{\prime }\)-(N-methylpyridinium)-\(2{,}2^{\prime }{:}6^{\prime }{,}2^{\prime \prime }\) terpyridine complexes

Abstract

Mononuclear Cu(II) pyridinium terpyridine based compounds, viz., [Cu(q- pytpy)(I)\((\hbox {CH}_{3}\hbox {COO})](\hbox {I})\cdot (2\hbox {H}_{2}\hbox {O})\) (1) and [Cu(dipp)(dippH)(q-pytpy)]\({\cdot }(2\hbox {H}_{2}\hbox {O}\))(DMF) (2) were isolated by reacting \(\hbox {Cu}(\hbox {OAc})_{2}{\cdot }\hbox {H}_{2}\hbox {O}\) with \(4^{\prime }\)-(N-methylpyridinium)-2,\(2^{\prime }{:}6^{\prime }{,}2^{\prime \prime }\)-terpyridine (q-pytpy) in the presence of 2,6 diisopropylphenyl phosphate (\(\hbox {dippH}_{2}\)). Both the new compounds were isolated as single crystals and characterised by spectroscopic (IR, ESI-MS, EPR, UV–Vis), thermogravimetric and microanalytical techniques. The molecular structures of both the compounds were determined in the solid-state by single crystal X-ray diffraction studies. Complexes 1 and 2 were evaluated for their nuclease and in vitro anti-tumor activities against human breast and colorectal cancer cell lines. The DNA cleavage and cytotoxic assays revealed that both 1 and 2 are effective in cleaving DNA, while the cytotoxic activity of 1 is better than 2 in both human colon and breast cancer cell lines.

Graphical Abstract

SYNOPSIS New phosphate-free and phosphate containing mononuclear pyridinium terpyridine-based Cu (II) compounds, isolated from a single reaction, have been demonstrated as anti-proliferative agents in human colon and breast cancer lines.

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Acknowledgements

This work was supported by (1) DST Nanomission (SR/NM/NS-1119/2011), (2) SERB, New Delhi (SB/S1/IC-48/2013) and (3) IIT-Bombay Bridge Funding. R. M. thanks SERB (SB/S2/JCB-85/2014), New Delhi for a J. C. Bose Fellowship, G.A.B thanks UGC New Delhi for a research fellowship. The authors thank Dr. Sandeep Kumar Gupta for help in solving one crystal structure.

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Correspondence to Ramaswamy Murugavel.

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Bhat, G.A., Maqbool, R. & Murugavel, R. Synthesis, characterisation, nuclease and cytotoxic activity of phosphate-free and phosphate-containing copper \(4^{\prime }\)-(N-methylpyridinium)-\(2{,}2^{\prime }{:}6^{\prime }{,}2^{\prime \prime }\) terpyridine complexes. J Chem Sci 130, 21 (2018). https://doi.org/10.1007/s12039-018-1422-7

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Keywords

  • Pyridinium terpyridine
  • X-ray structures
  • DNA cleavage
  • cytotoxic activity