Synthesis and photodynamic properties of amphiphilic A3B-phthalocyanine derivatives bearing N-heterocycles as potential cationic phototerapeutic agents

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

DYES AND PIGMENTS

ELSEVIER SCI LTD

Lugar: Oxford, England; Año: 2011 vol. 91 p. 6 - 12

0143-7208

Unsymmetrically substituted A3B-phthalocyanine derivatives bearing annulated 6-memberedN-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted witha 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)phthalocyaninederivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied inN,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluatedin Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthalocyaninesrepresent interesting agents with potential applications in photodynamic inactivation ofmicroorganisms.3B-phthalocyanine derivatives bearing annulated 6-memberedN-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted witha 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)phthalocyaninederivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied inN,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluatedin Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthalocyaninesrepresent interesting agents with potential applications in photodynamic inactivation ofmicroorganisms. 3B-phthalocyanine derivatives bearing annulated 6-memberedN-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted witha 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)phthalocyaninederivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied inN,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluatedin Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthalocyaninesrepresent interesting agents with potential applications in photodynamic inactivation ofmicroorganisms.