Synthesis And Photodynamic Properties Of Amphiphilic A3b-Phthalocyanine Derivatives Bearing N-Heterocycles As Potential Cationic Phototherapeutic Agents

TOMAS C. TEMPESTI; M. GABRIELA ALVAREZ; EDGARDO N. DURANTINI

ELSEVIER SCI LTD

Año: 2011 vol. 91 p. 6 - 6

nsymmetrically substituted A3B-phthalocyanine derivatives bearing annulated 6-membered N-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron (III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted with a range of 1,2-phthalonitrile derivatives in presence of 8-diazabicyclo[5.4.0]undec-7-ene to form the A3Bphthalocyanine. The reactions were carried out in DMSO/1-chloronaphthalene at 130e140 C for 15 h. This synthetic strategy resulted in phthalocyanines in 37e42% yield that required only simple purification. Annulated 6-membered N-heterocycles were methylated to obtain cationic Zn(II)phthalocyanine derivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied in N,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluated in Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthaloc