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Research articles

ScienceAsia 48 (2022):ID 776-781 |doi: 10.2306/scienceasia1513-1874.2022.113


Development of lipoyl-substituted porphyrins as novel biocompatible mitochondria-targeting agents


Apiratt Thitimona, Vitavat Aksornkittib, Amornpun Sereemaspunb, Patchanita Thamyongkita, Vinich Promarakc, Rojrit Rojanathanesa,*

 
ABSTRACT:     This work describeed synthesis and investigation of a novel water-soluble lipoyl-substituted porphyrin derivative and its Mn(III)-complex for mitochondria-targeting activities. The freebase derivative was obtained in moderate yield from alkylation of 5,10,15,20-tetra(4-pyridyl)porphyrin followed by amidation with lipoic acid anhydride. Mn-metallation of the freebase derivative quantitatively produced the target Mn(III)-porphyrin. Both lipoyl-substituted porphyrin and Mn(III)-complex were fully characterized by NMR spectroscopy, mass spectrometry, absorption spectrophotometry, and emission spectrophotometry. Both compounds were considered to have low cytotoxicity with IC50 values of 29?49 and more than 78 ?M, respectively, against the HaCaT and HDFa cells. In addition, mitochondria- targeting evaluation suggested that these target porphyrin derivatives exhibited accumulation, specifically in the mitochondria of the HaCaT cells.

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a Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330 Thailand
b Nanomedicine Research Unit, Department of Anatomy, Faculty of Medicine, Chulalongkorn University, Bangkok 10330 Thailand
c School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), Rayong 21210 Thailand

* Corresponding author, E-mail: rojrit@hotmail.com

Received 13 Mar 2022, Accepted 1 Jun 2022