Issue 12, 2014

Synthesis, properties and drug potential of the photosensitive alkyl- and alkylsiloxy-ligated silicon phthalocyanine Pc 227

Abstract

The photosensitive, alkyl- and alkylsiloxy-ligated silicon phthalocyanine, SiPc[(CH2)3SH][OSi(CH3)2(CH2)3N(CH3)2], Pc 227, has been prepared and characterized. This phthalocyanine yields the experimental photodynamic therapy (PDT) drug Pc 4, SiPc[OH][OSi(CH3)2(CH2)3N(CH3)2], when irradiated with red light. To provide an understanding of the process by which Pc 227 and other alkyl-alkylsiloxysilicon phthalocyanines such as Pc 227 are photolyzed, bond dissociation energy, natural bond orbital (NBO) charge distribution, spin density distribution, nucleus-independent chemical shift (NICS), and electron localization function (ELF) calculations have been carried out on two models related to it. These show that the lowest energy pathway for the photolysis of Pc 227 is a homolysis involving a phthalocyanine π radical having a low SiPc–C bond dissociation energy. The promise of the results of this study for synthetic chemistry and drug development is discussed.

Graphical abstract: Synthesis, properties and drug potential of the photosensitive alkyl- and alkylsiloxy-ligated silicon phthalocyanine Pc 227

Article information

Article type
Paper
Submitted
21 Aug 2014
Accepted
27 Sep 2014
First published
29 Sep 2014

Photochem. Photobiol. Sci., 2014,13, 1690-1698

Author version available

Synthesis, properties and drug potential of the photosensitive alkyl- and alkylsiloxy-ligated silicon phthalocyanine Pc 227

J. Li, Y. Yang, P. Zhang, J. R. Sounik and M. E. Kenney, Photochem. Photobiol. Sci., 2014, 13, 1690 DOI: 10.1039/C4PP00321G

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