Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico-Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

ORCiD

Nejat Düzgüneş: 0000-0001-6159-1391

Department

Biomedical Sciences

Document Type

Article

Publication Title

ChemPlusChem

ISSN

2192-6506

Volume

81

Issue

5

DOI

10.1002/cplu.201600051

First Page

460

Last Page

470

Publication Date

5-1-2016

Abstract

Sulfanyl porphyrazines substituted at their periphery with different dendrimeric moieties up to their first generation were synthesized and characterized by photochemical and biological methods. The presence of a dendrimeric periphery enhanced the spectral properties of the porphyrazines studied. The singlet-oxygen-generation quantum yield of the obtained macrocycles ranged from 0.02 to 0.20 and was strongly dependent on the symmetry of the compounds and the terminal groups of the dendritic outer shell. The in vitro biological effects of three most promising tribenzoporphyrazines were examined; the results indicated their potential as photosensitizers for photodynamic therapy (PDT) against two oral squamous cell carcinoma cell lines derived from the tongue. The highest photocytotoxicity was found for sulfanyl tribenzoporphyrazine that possessed 4-[3,5-di(hydroxymethyl)phenoxy]butyl substituents with nanomolar IC50 values at 10 and 42 nm against CAL 27 and HSC-3 cell lines, respectively. Topic of cancer: Sulfanyl porphyrazines and tribenzoporphyrazines substituted at their periphery with different dendrimeric moieties up to their first generation were synthesized and characterized by photochemical and biological methods. The in vitro biological effects of three most promising tribenzoporphyrazines were examined and found to exhibit nanomolar IC50 values (see figure).

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