Efficient synthesis and evaluation of bis-pyridinium/bis-quinolinium metallosalophens as antibiotic and antitumor candidates

• Published in: Journal of molecular structure 2017-01, Vol.1128, p.162-173
• Main Authors: Elshaarawy, Reda F.M., Eldeen, Ibrahim M., Hassan, Eman M.
• Format: Article
• Language: English
• Subjects: Anticancer; Antimicrobial; Metallosalophens; Pyridinium; Salophens
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2016.08.059

Inspired with the pharmacological diversity of salophens and in our endeavor to explore a new strategy which may conflict the invasion of drug resistance, we report herein efficient synthetic routes for the synthesis of new RO-salophen(Cl), pyridinium/quinolinium-based salophens (3a-e) and metallosalophens (4a-j). These new architectures have been structurally characterized by elemental and spectral analysis as well pharmacologically evaluated for their in vitro antimicrobial, against a common panel of pathogenic bacterial and fungal strains, and anticancer activities against human colon carcinoma (HCT-116) cell lines. Antimicrobial assay results revealed that all tested compounds exhibited moderate to superb broad-spectrum efficacy in comparison to the standard antibiotic with a preferential ability to perform as a fungicides than to act as bactericides. Noteworthy, VO(II)-salophens are more effective in reduction HCT-116 cell viability than Cu(II)-salophens. For example, VO(II)-salophen3 (4f) (IC50 = 2.13 μg/mL) was ca. 10-fold more efficient than Cu(II)-salophen3 (4e) (IC50 = 20.30 μg/mL). [Display omitted] •RO-, pyridinium- and quinolinium-salophens were prepared and characterized.•Copper(II) and oxovanadium(IV) complexes of these salophens have been fabricated.•In vitro antimicrobial and anticancer assay of new compounds have been addressed.•Antimicrobial assay results revealed a moderate to superb broad-spectrum efficacy.•VO(II)-salophens are more cytotoxic HCT-116 cell lines than Cu(II)-salophens.