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Issue 34, 2020
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Improved water solubility and photodynamic activity of hydroxy-modified porphyrins by complexation with cyclodextrin

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Abstract

Porphyrin derivatives with hydroxyphenyl or dihydroxyphenyl moieties in the meso-position were able to dissolve in water by complexation with two trimethyl-β-cyclodextrins (TMe-β-CDxs) without further chemical modification of porphyrins or addition of dimethyl sulfoxide as a co-solvent. TMe-β-CDx-complexed tetra(hydroxyphenyl)porphyrins (THPPs) with phenols in meso-positions have a much higher photodynamic activity than TMe-β-CDx-complexed tetrakis(dihydroxyphenyl)porphyrins (TDHPPs) with dihydroxyphenyl in the meso-position. The main reason for the different photoactivity is due to the intracellular uptakes of these complexes. Thus phenols in meso-positions of porphyrin derivatives in the complexes were recognized by HeLa cell receptors. Furthermore, the photodynamic activity of TMe-β-CDx-complexed THPP was much higher than that of THPP injected as a dimethyl sulfoxide solution.

Graphical abstract: Improved water solubility and photodynamic activity of hydroxy-modified porphyrins by complexation with cyclodextrin

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Supplementary files

Article information


Submitted
06 Jul 2020
Accepted
18 Aug 2020
First published
19 Aug 2020

Org. Biomol. Chem., 2020,18, 6702-6709
Article type
Paper

Improved water solubility and photodynamic activity of hydroxy-modified porphyrins by complexation with cyclodextrin

T. Yumoto, S. Satake, S. Hino, K. Sugikawa, R. Kawasaki and A. Ikeda, Org. Biomol. Chem., 2020, 18, 6702
DOI: 10.1039/D0OB01379J

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