Malaysian Journal of Analytical Sciences Vol 23 No 2 (2019): 263 - 273

DOI: 10.17576/mjas-2019-2302-11

 

 

 

SYNTHESIS AND CHARACTERIZATION OF BENZOHYDROXAMIC ACID AND METHYLBENZOHYDROXAMIC ACID METAL COMPLEXES AND THEIR CYTOTOXICTY STUDY

 

(Sintesis dan Pencirian Kompleks Logam Asid Benzohidroksamik dan Asid Metilbenzohidroksamik serta Kajian Sitotoksik)

 

Latifah Robbaniyyah Hassan1, Hadariah Bahron1, Kalavathy Ramasamy3, Amalina Mohd Tajuddin1,2*

 

1Faculty of Applied Sciences,

Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia

2Atta-ur-Rahman Institute for Natural Product Discovery

3Faculty of Pharmacy

Universiti Teknologi MARA, 42300 Bandar Puncak Alam, Selangor, Malaysia

 

*Corresponding author:  amalina9487@salam.uitm.edu.my

 

 

Received: 29 August 2017; Accepted: 14 March 2019

 

 

Abstract

Hydroxamic acids, RCONHOH, are electronically flexible compounds for organic and inorganic analyses due to their more delicate structures compared to carboxylic acid. These acids are easy to deprotonate to produce hydroxamate ions. The syntheses, physico-chemical and characterization of benzohydroxamic acid (BHA) and methylbenzohydroxamic acid (CH3-BHA) and their metal complexes VO(IV), Cr(III) and Ni(II) are reported herein. The metal complexes were synthesized by condensation reaction of BHA and CH3BHA with metal salts in 2:1 molar ratio. The compounds were characterized by elemental analysis, infrared spectroscopy (IR), 1H and 13C NMR, UV-Vis, TGA, magnetic susceptibility and molar conductance. From IR and magnetic susceptibility data, each complex is coordinated to the metal via oxygen and oxygen (O,O) in bidentate manner. The geometry of all metal complexes is octahedral except for [VO(BHA)2] that is square-pyramidal. The molar conductance values suggested that all complexes are non-electrolytic. A cytotoxicity study against human colorectal cancer, HCT116 cell lines, revealed that all the complexes are better anticancer agents than their parent ligands.

 

Keywords:  hydroxamic acid, vanadium(IV), chromium(III), nickel(II), cytotoxicity

 

Abstrak

Asid hidroksamik, RCONHOH, adalah sebatian yang anjal elektronik untuk analisis organik and bukan organik kerana strukturnya yang lebih rapuh jika dibandingkan dengan asid karboksilat. Asid ini mudah untuk deprotonasi untuk menghasilkan ion hidrosamat. Sintesis, fizikokimia dan  pencirian asid benzohidroksamik (BHA) dan asid metilbenzohidroksamik (CH3-BHA) dan logam kompleksnya VO(IV), Cr(III) dan Ni(II) telah dilaporkan disini. Logam kompleks telah disintesis melalui kondensasi antara BHA dan CH3-BHA dengan garam logam dalam nisbah molar 2:1. Semua sebatian yang dihasilkan telah dicirikan menggunakan analisis asas, spektroskopi inframerah (IR), 1H dan 13C NMR, UV-Vis, TGA, kerentanan magnet dan kekonduksian molar. Setiap kompleks logam berkoordinasi dengan logam melalui atom oksigen dan oksigen (O,O) dengan cara bidentat daripada data IR dan kerentanan magnet. Geometri untuk semua kompleks adalah geometri beroktahedron kecuali [VO(BHA)2] yang geometrinya adalah piramid segi empat sama. Semua kompleks logam adalah bukan elektrolit berdasarkan nilai kekonduksian molar. Kajian sitotoksik terhadap HCT116 menunjukkan bahawa semua kompleks logam adalah agen antikanser yang lebih baik daripada ligan induk mereka.

 

Kata kunci:  asid hidroksamik, vanadium(IV), kromium(III), nikel(II), sitotoksik

 

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