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- Title
Development of lipoyl-substituted porphyrins as novel biocompatible mitochondria-targeting agents.
- Authors
Thitimon, Apiratt; Aksornkitti, Vitavat; Sereemaspun, Amornpun; Thamyongkit, Patchanita; Promarak, Vinich; Rojanathanes, Rojrit
- 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 µM, 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.
- Subjects
PORPHYRINS; THIOUREA; LIPOIC acid; NUCLEAR magnetic resonance spectroscopy; MASS spectrometry; AMIDATION
- Publication
ScienceAsia, 2022, Vol 48, Issue 6, p776
- ISSN
1513-1874
- Publication type
Article
- DOI
10.2306/scienceasia1513-1874.2022.113