Spectroscopy, binding to liposomes and production of singlet oxygen by porphyrazines with modularly variable water solubility

Photochemistry and Photobiology
Alan SholtoBenjamin Ehrenberg

Abstract

Three novel classes of porphyrazine-like structures were synthesized to form modular structures in which lipophilicity and water solubility can be tuned. Subtle modification of solubility is an important criterion in selecting a compound for biological photosensitization. The general structure takes the form H2[pz(AnB4-n)], where the core is a porphyrazine (pz) group, A is a pyrrole ring with two sulfide linkages (SR moieties) and B is a pyrrole fused with a 4,7-bis(isopropyloxy)benzo group, with n=4, 3 and 2. These molecules possess their longest wavelength absorption band between 700 and 810 nm, hence laser beams of higher tissue penetration depth could be used to illuminate them in photodynamic therapy (PDT). Armed with absorption bands in the far-red and near-infrared (near-IR), and a capability to tune the solubility, these molecules could make for better sensitizers because of optimized uptake by lipidic membranes and better optical properties. We tested several derivatives of the A4, A3B and A2B2 structures for their singlet oxygen quantum yields in methanol and in liposomes, using 9,10-dimethyl anthracene (DMA) as a singlet oxygen target. Singlet oxygen quantum yields in liposomes ranged from 0.01 to 0.44, with the A2B2...Continue Reading

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Citations

Mar 31, 2009·European Biophysics Journal : EBJ·Shimshon Ben DrorBenjamin Ehrenberg
Jan 19, 2010·Proceedings of the National Academy of Sciences of the United States of America·Evan R TrivediBrian M Hoffman
Jan 16, 2010·Photochemistry and Photobiology·Evan R TrivediBrian M Hoffman
Jul 28, 2011·Photochemistry and Photobiology·Adaickapillai MahendranAlexander Greer
May 23, 2017·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Lixin ZangPeisong Meng
Feb 14, 2018·Photochemistry and Photobiology·Niluksha WalalawelaAlexander Greer
Aug 18, 2010·Physical Chemistry Chemical Physics : PCCP·Guo-Yu JiangBao-Wen Zhang
Feb 14, 2015·Journal of Materials Chemistry. B, Materials for Biology and Medicine·M Angeles IzquierdoMarina K Kuimova
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Nov 25, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Ke LiXuesong Wang
Dec 31, 2019·The Journal of Organic Chemistry·Esmeralda CaballeroM Salomé Rodríguez-Morgade

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