Synthesis and comparative photodynamic properties of two isosteric alkyl substituted zinc(II) phthalocyanines.

Abstract:

:The synthesis and photophysical parameters of two novel isosteric cationic zinc(II) phthalocyanines: 2,9(10),16(17),23(24)-tetrakis[(N-butyl-N-methylammoniumethylsulfanyl]phthalocyaninatozinc(II) tetraiodide (6) and 2,9(10),16(17),23(24)-tetrakis[(N-dibutyl-N-methylammonium)ethoxy]phthalocyaninatozinc(II) tetraiodide (7) were investigated. Maximum absorption values were 686.5 nm and 678 nm for 6 and 7, respectively, whereas singlet molecular oxygen generation was 0.42 and 0.67, respectively. The photodynamic effect and the cellular uptake of both phthalocyanines were evaluated on human nasopharynx KB carcinoma cells. After light exposure, phthalocyanine 6 showed a higher cytotoxic activity than 7. In addition, a higher intracellular uptake of 6 and a preferential localization within lysosomes were demonstrated. The production of a greater amount of reactive oxygen species after phthalocyanine 6 irradiation would be responsible for its potent phototoxic action on KB cells.

journal_name

Eur J Med Chem

authors

Gauna GA,Marino J,García Vior MC,Roguin LP,Awruch J

doi

10.1016/j.ejmech.2011.09.014

subject

Has Abstract

pub_date

2011-11-01 00:00:00

pages

5532-9

issue

11

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(11)00674-X

journal_volume

46

pub_type

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