Exploring copper (II) porphyrin complexes and their derivatives for electrochemical analysis and biological assessment in the study of breast cancer (MCF-7) cell lines

Supakorn Boonyuen; Paramasivam Shanmugam; Rajan Ramachandran; Tossapon Phromsatit; Thapong Teerawatananond; Supawan Tantayanon; Premjit Arpornmaeklong; Yuki Shirosaki

doi:10.1016/j.envres.2024.118489

Exploring copper (II) porphyrin complexes and their derivatives for electrochemical analysis and biological assessment in the study of breast cancer (MCF-7) cell lines

Environ Res. 2024 Feb 17:250:118489. doi: 10.1016/j.envres.2024.118489. Online ahead of print.

Authors

Supakorn Boonyuen¹, Paramasivam Shanmugam², Rajan Ramachandran³, Tossapon Phromsatit², Thapong Teerawatananond⁴, Supawan Tantayanon⁵, Premjit Arpornmaeklong⁶, Yuki Shirosaki⁷

Affiliations

¹ Department of Chemistry, Faculty of Science and Technology, Thammasat University, Pathumthani, 12120, Thailand. Electronic address: chemistrytu@gmail.com.
² Department of Chemistry, Faculty of Science and Technology, Thammasat University, Pathumthani, 12120, Thailand.
³ Center of Translational Medicine, Zibo Central Hospital, Zibo, 255036, Shandong, China.
⁴ Department of Chemistry, Faculty of Science and Technology, Valaya Alongkorn Rajabhat University, Pathumthani, 12120, Thailand.
⁵ Department of Chemistry, Green Chemistry Research Laboratory, Chulalongkorn University, Bangkok, 10330, Thailand.
⁶ Faculty of Dentistry, Thammasat University, Pathumthani, 12120, Thailand.
⁷ Department of Materials Science, Faculty of Engineering, Kyushu Institute of Technology, Kitakyushu, Japan.

PMID: 38373552
DOI: 10.1016/j.envres.2024.118489

Abstract

In this study, several derivatives of tetraphenylporphyrin were synthesized, each with unique meso-substituent groups including phenyl, methoxyphenyl, butyloxyphenyl, octyloxyphenyl, and dectyloxyphenyl. Additionally, their corresponding copper complexes were prepared and thoroughly characterized. The structural confirmation of all compounds was established through CHN elemental analysis, mass spectrometry, and FT-IR spectroscopy. As the number of carbon atoms in the alkyl long-chain increased, a slight red shift in the electronic absorption band was observed, which was attributed to the electronic influence of the alkyl group. DFT analysis indicated that electron density predominantly localized on the porphyrin ring of both the metal free porphyrins and copper (II) porphyrin complexes, with relatively low electron density in the p orbital of the meso-aryl long-chain substituent group. EPR spectroscopy of the Copper (II) ion complexes revealed signals, indicating their paramagnetic properties. Additionally, the Copper (II) tetraphenylporphyrin (CuTPP) complexes displayed two reversible oxidation peaks at +0.97 V and +1.35 V, whereas other derivatives exhibited lower oxidation potentials. The cytotoxicity of these compounds against MCF-7 cell lines was assessed using MTT assay, revealing cytotoxic effects in all cases. Among them, Copper (II) tetrakis (4-methyloxyphenyl)porphyrin (CuTOMPP) demonstrated the highest potential, with an IC₅₀ value of 32.07 μg/mL.

Keywords: Cu(II)porphyrins; Cytotoxicity; Electrochemistry; MCF-7.