Abstract
The literature on the synthesis and the biological properties of boron-containing chlorins and phthalocyanines is reviewed. A series of homologous derivatives of pyropheophorbide A is described. The compounds contain the B12H11SH2- cluster attached to the single carboxyl group and vary in the length of the alkyl chain (methyl, propyl, pentyl, heptyl and nonyl) attached via an ether linkage to the former vinyl group. Cellular uptake was found for all derivatives except the nonyl sidechain. The compounds were moderately cell-toxic. Localization in lysosomes could be excluded; the compounds localized probably in the mitochondria.
Keywords: Porphyrin, chlorin, phthalocyanine, porphyrazine, carborane, dodecaborate, cell uptake
Anti-Cancer Agents in Medicinal Chemistry
Title: Boron-Containing Chlorins and Tetraazaporphyrins: Synthesis and Cell Uptake of Boronated Pyropheophorbide A Derivatives
Volume: 6 Issue: 2
Author(s): Michal Ratajski, Jens Osterloh and Detlef Gabel
Affiliation:
Keywords: Porphyrin, chlorin, phthalocyanine, porphyrazine, carborane, dodecaborate, cell uptake
Abstract: The literature on the synthesis and the biological properties of boron-containing chlorins and phthalocyanines is reviewed. A series of homologous derivatives of pyropheophorbide A is described. The compounds contain the B12H11SH2- cluster attached to the single carboxyl group and vary in the length of the alkyl chain (methyl, propyl, pentyl, heptyl and nonyl) attached via an ether linkage to the former vinyl group. Cellular uptake was found for all derivatives except the nonyl sidechain. The compounds were moderately cell-toxic. Localization in lysosomes could be excluded; the compounds localized probably in the mitochondria.
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Ratajski Michal, Osterloh Jens and Gabel Detlef, Boron-Containing Chlorins and Tetraazaporphyrins: Synthesis and Cell Uptake of Boronated Pyropheophorbide A Derivatives, Anti-Cancer Agents in Medicinal Chemistry 2006; 6 (2) . https://dx.doi.org/10.2174/187152006776119126
DOI https://dx.doi.org/10.2174/187152006776119126 |
Print ISSN 1871-5206 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5992 |
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