Antifungal activity of [alpha]-methyl trans cinnamaldehyde, its ligand and metal complexes: promising growth and ergosterol inhibitors

• Published in: Biometals Vol. 24; no. 5; p. 923
• Main Authors: Shreaz, Sheikh, Sheikh, Rayees A, Bhatia, Rimple, Neelofar, Khan, Imran, Sheikh, Hashmi, Athar A, Manzoor, Nikhat, Basir, Seemi F, Khan, Luqman A
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Nature B.V 01.10.2011
• Subjects: Aldehydes; Biosynthesis; Fungal infections; Metal complexes; Metals; Nickel; Yeast
• ISSN: 0966-0844; 1572-8773
• DOI: 10.1007/s10534-011-9447-0

Antifungal effectivity and utility of cinnamaldehyde is limited because of its high MIC and skin sensitivity. In this study, α-methyl trans cinnamaldehyde, a less irritating derivative, have been self coupled and complexed with Co(II) and Ni(II) to generate N, N'-Bis (α-methyl trans cinnamadehyde) ethylenediimine [C^sub 22^H^sub 24^N2], [Co(C^sub 44^H^sub 48^N^sub 4^)Cl^sub 2^] and [Ni(C^sub 44^H^sub 48^N^sub 4^)Cl^sub 2^]. Ligand and complexes were characterized on the basis of FTIR, ESI-MS, IR and ^sup 1^HNMR techniques. Synthesized ligand [L] and complexes were investigated for their MICs, inhibition of ergosterol biosynthesis and H^sup +^ extrusion against three strains of Candida: C. albicans 44829, C. tropicalis 750 and C. krusei 6258. Average of three species MIC of methyl cinnamaldehyde is 317 μg/ml (2168 μM). Compared to methyl cinnamaldehyde ligand [L], Co(II) and Ni(II) complex are found to be 4.48, 17.78 and 21.46 times more effective in liquid medium and 2.73, 8.93 and 10.38 times more effective in solid medium. At their respective MIC^sub 90^ average inhibition of ergosterol biosynthesis caused by methyl cinnamaldehyde, ligand [L], Co(II) and Ni(II) complex, respectively was 80, 78, 90 and 93%. H^sup +^ extrusion was also significantly inhibited but did not co-relate well with MIC^sub 90^. Results indicate ergosterol biosynthesis as site of action of α-methyl cinnamaldehyde, synthesized ligand and complexes. α-methyl cinnamaldehyde and ligand did not show any toxicity against H9c2 rat cardiac myoblast cell, whereas Co(II) and Ni(II) complexes on an average produced 19% cellular toxicity.[PUBLICATION ABSTRACT]