Synthesis and Comparison of Biological Activity of Some Unsymmetrical Porphyrine Derivatives

Abstract

Here, two newly synthesized asymmetric porphyrin derivative molecules, along with their characterization and biological activity studies, are reported for the first time.The use of two different aldehyde molecules is necessary to obtain asymmetric porphyrin derivatives, and the reaction rates of these molecules are crucial for the success of the synthesis. The structures obtained were confirmed by 1H NMR, IR and uV-Vis spectroscopy. It was thought that different substituents with shared atoms could lead to changes in biological activity. Therefore, studies were conducted to investigate the effect of substituents. Both molecules contain tetraphenyl groups, three of which carry tert-butyl groups, and the fourth contains fluorine and trifluoromethyl substituents. The PORF molecule contains a fluorine atom in the meta position, while PORF3 has a trifluoromethyl group in the para position. The antioxidant activities of the porphyrin molecules were evaluated using five different spectrophotometric methods. In all antioxidant tests, the PORF3 molecule was found to exhibit higher activity compared to the PORF molecule. At a concentration of 100 µg/mL, PORF3 and PORF molecules showed 19.08 ± 0.78 % and 17.22 ± 0.35 % inhibition of acetylcholinesterase (AChE); 25.43 ± 0.56 % and 20.29 ± 0.83 % inhibition of butyrylcholinesterase (BChE), respectively. On the other hand, tyrosinase enzyme inhibition results revealed that both porphyrin molecules exhibited moderate activity, with inhibition values being found as 38.22 ± 0.63 % for PORF and 41.74 ± 0.40 % for PORF3.

Keywords

• Porphyrin
• Antioxidant
• Anticholinesterase
• Antityrosinase

Supporting Institution

Mugla Sitki Kocman University

Project Number

21/120/06/1/4

Thanks

The synthesis study was supported by the Scientific Research Projects Coordination Unit (BAP) of Muğla Sıtkı Koçman University with project number 21/120/06/1/4.

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