Synthesis and characterization of novel 5-monocarbohydrate-10,20-bis-aryl-porphyrins

abstract

The synthesis of derivatives bearing glucose or galactose units linked by an acrylate spacer to one free meso position of a bis-aryl-porphyrin macrocycle was developed and characterized by standard spectroscopic techniques. The new mono-substituted gluco- and galacto-porphyrin derivatives 5-8 present an alternative to the widespread tetra-aryl porphyrin functionalization. Singlet oxygen studies showed a comparable singlet oxygen production with TPP. Furthermore, the less bulky architectures here synthesized present an opportunity to enhance the PDT and PDI capabilities of glycoporphyrins with a simple synthetic modification at one of the meso positions.

keywords

PHOTODYNAMIC ACTIVITY; PORPHYRINS; DERIVATIVES; PHTHALOCYANINES; PHOTOSENSITIZERS; INACTIVATION; THERAPY; CHLORIN

subject category

Chemistry

authors

Figueira, F; Lourenco, LMO; Neves, MGPMS; Cavaleiro, JAS; Tome, JPC

our authors

acknowledgements

We wish to thank Fundacao para a Ciencia e a Tecnologia (FCT, Portugal), the European Union, QREN, FEDER through Programa Operacional Factores de Competitividade (COMPETE), QOPNA (FCT UID/QUI/00062/2019) and CQE (FCT UID/QUI/0100/2019) research units, financed by national funds through the FCT/MEC and when appropriate co-financed by FEDER under the PT2020 Partnership Agreement. The research contracts of F. Figueira (REF. -168-89-ARH/2018) is funded by national funds (OE), through FCT Fundacao para a Ciencia e Tecnologia, I.P., in the scope of the framework contract foreseen in the numbers 4, 5 and 6 of the article 23, of the Decree-Law 57/2016, of August 29, changed by Law 57/2017, of July 19.

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