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A study of structure–activity relationship and anion-controlled quinolinyl Ag(I) complexes as antimicrobial and antioxidant agents as well as their interaction with macromolecules

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Abstract

In this communication, we feature the synthesis and in-depth characterization of a series of silver(I) complexes obtained from the complexation of quinolin-4-yl Schiff base ligands ((E)-2-((quinolin-4-ylmethylene)amino)phenol La, 2-(quinolin-4-yl)benzo[d]thiazole Lb, (E)-N-(2-fluorophenyl)-1-(quinolin-4-yl)methanimine Lc, (E)-N-(4-chlorophenyl)-1-(quinolin-4-yl)methanimine Ld, (E)-1-(quinolin-4-yl)-N-(p-tolyl)methanimine Le, (E)-1-(quinolin-4-yl)-N-(thiophen-2-ylmethyl)methanimine Lf) and three different silver(I) anions (nitrate, perchlorate and triflate). Structurally, the complexes adopted different coordination geometries, which included distorted linear or distorted tetrahedral geometry. The complexes were evaluated in vitro for their potential antibacterial and antioxidant activities. In addition, their interactions with calf thymus-DNA (CT-DNA) and bovine serum albumin (BSA) were evaluated. All the complexes had a wide spectrum of effective antibacterial activity against gram-positive and gram-negative bacterial and good antioxidant properties. The interactions of the complexes with CT-DNA and BSA were observed to occur either through intercalation or through a minor groove binder, while the interaction of the complexes with BSA reveals that some of the complexes can strongly quench the fluorescence of BSA through the static mechanism. The molecular docking studies of the complexes were also done to further elucidate the modes of interaction with CT-DNA and BSA.

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Abbreviations

BSA:

Bovine serum albumin

CLSI:

Clinical and Laboratory Standards Institute

CT-DNA:

Calf-thymus deoxyribonucleic acid

DMSO:

Dimethyl sulfoxide

DNA:

Deoxyribonucleic acid

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

EB:

Ethidium bromide

H342:

Hoechst 33342

FRAP:

Ferric reducing antioxidant power

IC50 :

50% Inhibitory concentration

MHA:

Müeller–Hinton agar

MIC:

Minimum inhibitory concentration

MRSA:

Methicillin-resistant staphylococcus aureus

NB:

Nutrient broth

RNA:

Ribonucleic acid

ROSs:

Reactive oxygen species

TPTZ:

Tripyridyltriazine

Trp:

Tryptophan

Tyr:

Tyrosine

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Acknowledgements

Ms Adesola A. Adeleke acknowledges Olabisi Onabanjo University, Ago-Iwoye, for granting her study leave to pursue the Ph.D. Programme at the University of KwaZulu-Natal. The authors would like to appreciate the University of KwaZulu-Natal and the National Research Foundation of South Africa (Grant Number 119342) for their financial assistance for Ms. Adesola A. Adeleke.

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Correspondence to Bernard Omondi.

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Adeleke, A.A., Zamisa, S.J., Islam, M.S. et al. A study of structure–activity relationship and anion-controlled quinolinyl Ag(I) complexes as antimicrobial and antioxidant agents as well as their interaction with macromolecules. Biometals 35, 363–394 (2022). https://doi.org/10.1007/s10534-022-00377-6

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  • DOI: https://doi.org/10.1007/s10534-022-00377-6

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