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
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* Corresponding author, E-mail: rojrit@hotmail.com
Received 13 Mar 2022, Accepted 1 Jun 2022
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