Antineoplastic Activity of Alkylaminolapachol Analogues and their Copper Complexes against MDA-MB-231 Human Breast Cancer Cell Lines

O.B. Pawar; K.V. Sanas; R.B. Patwardhan; S.A. Waghmode; M.Y. Khaladkar

doi:10.14233/ajchem.2020.22496

Issue

Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020

Issue Published : February 25, 2020

This work is licensed under a Creative Commons Attribution 4.0 International License.

Antineoplastic Activity of Alkylaminolapachol Analogues and their Copper Complexes against MDA-MB-231 Human Breast Cancer Cell Lines

https://doi.org/10.14233/ajchem.2020.22496

O.B. Pawar

Department of Applied Science, College of Engineering Pune, Pune-411005, India

K.V. Sanas

Department of Applied Science, College of Engineering Pune, Pune-411005, India

R.B. Patwardhan

Department of Microbiology, Haribhai V. Desai College, Pune-411002, India

S.A. Waghmode

Department of Chemistry, M.E.S. Abasaheb Garware College, Pune-411004, India

M.Y. Khaladkar

Department of Applied Science, College of Engineering Pune, Pune-411005, India

Corresponding Author(s) : M.Y. Khaladkar

myk.appsci@coep.ac.in

Asian Journal of Chemistry, Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020
Article Published : February 25, 2020

Abstract

In present study, three alkylamino substituted hydroxynaphthoquinone analogues of naturally occurring bioactive lapachol are synthesized. Further, copper(II) complexes of these ligands have been synthesized using hassle free modified grindstone method. Both ligands and copper(II) complexes were characterized using UV-visible spectroscopy, FTIR, elemental analysis and NMR spectra. Cell viability assay of the compound was carried out against growth of MDA-MB-231 human breast cancer cell lines. A better tumorocidal activity was observed for ligands and their copper(II) complexes in concentration of 2.95 to 0.11 mmol/L. Antineoplastic activity of copper(II) complexes was found to be more than parent ligands. Antimicrobial assay results showed that compound exhibit better activity against organisms under study. Antimicrobial susceptibility of compounds was carried out against culture of E. coli K12 (RP4), B. subtilis (pUB110), K. pneumoniae and S. paratyphi. The lowest MIC of < 0.20 mg/mL was obtained for L-3 against S. paratyphi. Cyclic voltammetry of ligand and complexes performed in non-aqueous system shows that ligand exhibits classical two step redox couple corresponds to the formation of semiquinone and catechole moieties in solution state at characteristic potential values. Whereas cyclic voltammogram of copper(II) complexes exhibit additional peak at characteristic potential corresponds to reversible redox reaction of central Cu(II) ion in complexes.

Keywords

Antineoplastic activity Lapachol Antimicrobial activity Copper(II) complexes

Pawar, O., Sanas, K., Patwardhan, R., Waghmode, S., & Khaladkar, M. (2020). Antineoplastic Activity of Alkylaminolapachol Analogues and their Copper Complexes against MDA-MB-231 Human Breast Cancer Cell Lines. Asian Journal of Chemistry, 32(4), 887–895. https://doi.org/10.14233/ajchem.2020.22496

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S.R. Paiva, L.A. Lima, M.R. Figueiredo and M.A.C. Kaplan, An. Acad. Bras. Cienc., 76, 499 (2004); https://doi.org/10.1590/S0001-37652004000300004

S. Padhye, P. Dandawate, M. Yusufi, A. Ahmad and F.H. Sarkar, Med. Res. Rev., 32, 1131 (2012); https://doi.org/10.1002/med.20235

A.V. Pinto and S.L. de Castro, Molecules, 14, 4570 (2009); https://doi.org/10.3390/molecules14114570

B. Kiran Aithal, M.R. Sunil Kumar, B. Nageshwar Rao, N. Udupa and B.S. Satish Rao, Cell Biol. Int., 33, 1039 (2009); https://doi.org/10.1016/j.cellbi.2009.06.018

S.M.G. Sayeed, S.A. Sayeed, S. Ashraf, S. Naz, R. Siddiqi, R. Ali and M.A. Mesaik, Pak. J. Bot., 45, 1431 (2013).

L.I. Lopez-Lopez, S.D.N. Nery-Flores, S.Y. Silva-Belmares and A. SaenzGalindo, Vitae Rev. Fac. Quim. Farm., 21, 248 (2014).

M.A. Souza, S. Johann, L.A.R.S. Lima, F.F. Campos, I.C. Mendes, H. Beraldo, E.M. Souza-Fagundes, P.S. Cisalpino, C.A. Rosa, T.M.A. Alves, N.P. Sa and C.L. Zani, Mem. Inst. Oswaldo Cruz, 108, 342 (2013); https://doi.org/10.1590/S0074-02762013000300013

D.L. Stout and F.F. Becker, Cancer Res., 46, 2693 (1986).

D.R. Williams, Chem. Rev., 72, 203 (1972); https://doi.org/10.1021/cr60277a001

M.J. Seven and L.A. Johnson, Metal Binding in Medicine, Lippincott Co.: Philadelphia P.A., edn 4 (1960).

D.R. Williams, The Metal of Life: The Solution Chemistry of Metal ions in Biological System, Van Nostrand: London (1971).

M.J. Cleare and J.D. Hoeschele, Bioinorg. Chem., 2, 187 (1973); https://doi.org/10.1016/S0006-3061(00)80249-5

A. Furst, The Chemistry of Chelation in Cancer, Springfield: Illinois, edn 3 (1963).

Z.F. Plyta, T. Li, V.P. Papageorgiou, A.S. Mellidis, A.N. Assimopoulou, E.N. Pitsinos and E.A. Couladouros, Bioorg. Med. Chem. Lett., 8, 3385 (1998); https://doi.org/10.1016/S0960-894X(98)00600-3

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M.H. Kollef and V.J. Fraser, Ann. Intern. Med., 134, 298 (2001); https://doi.org/10.7326/0003-4819-134-4-200102200-00014

H.H. Thorp, J.E. Sarneski, G.W. Brudvig and R.H. Crabtree, J. Am. Chem. Soc., 111, 9249 (1989); https://doi.org/10.1021/ja00208a029

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S. Salunke-Gawali, S. Rane, K. Boukheddaden, E. Codjovi, J. Linares, F. Varret and P. Bakar, Indian J. Chem., 43A, 2563 (2004).

O. Pawar, A. Patekar, A. Khan, L. Kathawate, S. Haram, G. Markad, V. Puranik and S. Salunke-Gawali, J. Mol. Struct., 1059, 68 (2014); https://doi.org/10.1016/j.molstruc.2013.11.029

M.O. Goulart, P. Falkowski, T. Ossowski and A. Liwo, Bioelectrochem., 59, 85 (2003); https://doi.org/10.1016/S1567-5394(03)00005-7

K. Manvizhi and K.R. Sankaran, Int. J. Sci. Res. Mod. Educ., 1, 171 (2016).

W. Luo, X.-G. Meng, J.-F. Xiang, Y. Duan, G.-Z. Cheng and Z.-P. Ji, Inorg. Chim. Acta, 361, 2667 (2008); https://doi.org/10.1016/j.ica.2007.11.030

C. Frontana, B.A. Frontana-Uribe and I. González, J. Electroanal. Chem., 573, 307 (2004); https://doi.org/10.1016/j.jelechem.2004.07.017

Issue

Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020

Antineoplastic Activity of Alkylaminolapachol Analogues and their Copper Complexes against MDA-MB-231 Human Breast Cancer Cell Lines

Corresponding Author(s) : M.Y. Khaladkar

Abstract

Keywords

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