Marmara Pharmaceutical Journal 2017 , Vol 21 , Issue 4
Antioxidant and cytotoxic properties of novel spirocyclic benzothiazolines
Gökçe CİHAN-ÜSTÜNDAĞ1,Nurten ÖZSOY2,Ezgi ÖZTAŞ3,Nilgün KARALI1,Gültaze ÇAPAN1
1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, Istanbul, 34116, Turkey
2Department of Biochemistry, Faculty of Pharmacy, Istanbul University, Istanbul, 34116, Turkey
3Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Istanbul University, Istanbul, 34116, Turkey
DOI : 10.12991/mpj.2017.33 In this work, we report the synthesis, structural characterization and evaluation of in vitro antioxidant and cytotoxic properties of novel spirobenzothiazolines (1a-e, 2a-e). 5-nonsubstituted spirobenzothiazolines (1a-e) demonstrated notable inhibitory capacity on lipid peroxidation (LPO), reducing power and scavinging effects on diphenylpicryl hydrazine (DPPH˙) and 2,2"-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid (ABTS˙+) radicals, that were similar to that of α-tocopherol. The most potent antioxidant was compound 1a (incorporating an ethyl group on the cyclohexane ring) with an anti-LPO activity 2-fold higher than that of α-tocopherol. Compound 1a exhibited anti-LPO and DPPH˙ scavenging activities at concentrations lower than those cytotoxic for mouse normal fibroblast (NIH/3T3) cells and was also found to be slightly more selective for cancer cells (human prostat adenocarcinoma cell/PC-3) than normal mammalian cells. Keywords : Benzothiazole; spiroheterocycle; antioxidant activity; cytotoxic activity