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Transition metal (II) complexes of hydrazones derived from tetralone: synthesis, spectral characterization, in vitro antimicrobial and cytotoxic studies

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Abstract

A series of transition metal (II) complexes with general formula [M(L1−4)2(H2O)2] (where M = Co(II), Ni(II), Cu(II) and Zn(II)) was synthesized by the reaction of metal(II) acetates with hydrazones [HL1–HL4] obtained from condensation of tetralone with hydrazide derivatives. The characterization of synthesized compounds (1–20) was done by using elemental analysis, different spectral studies (UV–Vis, 1H NMR, 13C NMR, FT-IR, mass, ESR and fluorescence), magnetic susceptibility, molar conductance measurement and thermal (DTA, TGA and DTG) analysis. The characterization results suggested the bidentate nature of the hydrazones, which chelate with the metal ion via nitrogen of (C=N) group and deprotonated carbonyl oxygen in the enolized form, resulting in stable, non-volatile octahedral complexes. The antimicrobial potential of the compounds was evaluated against four bacterial, i.e. (S. aureus, B. subtilis, P. aeruginosa and E. coli), and two fungal species, i.e. (A. niger and C. albicans), by a serial dilution method with complexes 15 and 16 as most active compounds against microbes. All the compounds were also tested for its cytotoxicity (in vitro) against three human cancer cell lines (A549, HeLa and MCF-7) and one normal cell line (L6) by the MTT assay, which focussed on an increased activity of compounds 7 and 15 towards A549, MCF-7 and HeLa cancer cell line with IC50 values ranging from 10.76 to 16.42 μg/mL, and compounds were found to be non-toxic towards L6 cell line as compared to the standard drug doxorubicin. The results demonstrated that complexation enhanced the biological activity of compounds.

Graphic abstract

The synthesized compounds (1–20) were screened for antitumor activities against A549, MCF7, Hela cancer cell lines. Copper complex (7) and (15) was found to be the most active antitumor agent and less toxic against L6—Rat myoblast normal cell line than standard doxorubicin.

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Abbreviations

DME:

M Dulbecco’s modified Eagle’s medium

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

DMSO-d6:

Deuterated dimethyl sulfoxide

ESR:

Electron spin resonance

TGA:

Thermal gravimetric analysis

DTA:

Differential thermal analysis

MS:

Mass spectra

FAB:

Fast atom bombardment

FT-IR:

Fourier transform infrared spectroscopy

A549:

Human lung carcinoma cell line

HeLa:

Human cervical carcinoma cell line

MCF7:

Human breast carcinoma cell line

L6 :

Rat myoblast cell line normal

MTT:

3-(4,5-Dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide

NMR:

Nuclear magnetic resonance

IC50 :

Concentration of drug required to inhibit the growth of 50% of tumour cells

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Acknowledgements

One of the authors Mr Som Sharma (JRF) is highly grateful to CSIR, New Delhi, India (No. 09/752(0060)/2016/EMR), for the grant of JRF scholarship and also thankful to Dr. A.P.J. Abdul Kalam Central Instrumentation Laboratory, and Department of Chemistry, GJUS&T, Hisar for supplying good facilities to perform this research work.

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Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, 125001, India

    J. Devi, S. Sharma & S. Kumar

  2. Department of Chemistry, Government College Hisar, Hisar, 125001, India

    S. Sharma

  3. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar, 125001, India

    D. K. Jindal

  4. Institute of Advanced Studies in Science & Technology, Life Science Division, Guwahati, 781035, Assam, India

    P. P. Dutta

  5. School of Pharmaceutical Sciences, Shoolini University, Solan, 173212, Himachal Pradesh, India

    D. Kumar

  6. Faculty of Pharmaceutical Science, Assam Down Town University, Panni khaiti, Guwahati, 781026, Assam, India

    P. P. Dutta

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Devi, J., Sharma, S., Kumar, S. et al. Transition metal (II) complexes of hydrazones derived from tetralone: synthesis, spectral characterization, in vitro antimicrobial and cytotoxic studies. Res Chem Intermed 47, 2433–2467 (2021). https://doi.org/10.1007/s11164-021-04413-x

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