Synthesis and photocytotoxicity of some new substituted phthalocyanines.
Some new, ring-substituted phthalocyanines have been synthesized and underwent preliminary testing for photodynamic activity using the colony forming ability of Chinese hamster cells in culture as an endpoint. Using 4-(3-N,N-diethylaminopropyl)phthalonitrile as a precursor, the previously unknown metal-free 2,9,16,23-tetra-(3-N,N-diethylaminopropyl)phthalocyanine was prepared and converted to its zinc (II) and its cationic water-soluble 2,9,16,23-tetramethylammonium zinc (II) iodide derivatives. Other new phthalocyanine derivatives tested, include a 2,9,16,23-tetra(2-hydroxymethyl-2-methylbutoxy)phthalocyaninato zinc (II) and 2,3,9,10,16,17,23,24-octahydroxyphthalocyaninato zinc (II) derivatives. Boron tribromide cleavage of the newly prepared and fully characterized 2,3,9,10,16,17,23,24-octamethoxyphthalocyanine gave the unstable metal-free octahydroxyphthalocyanine, which could only be characterized by ultraviolet-visible, NMR and IR spectroscopy.
Leznoff
C C
CC
Vigh
S
S
Svirskaya
P I
PI
Greenberg
S
S
Drew
D M
DM
Ben-Hur
E
E
Rosenthal
I
I
D000818:Animals; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects / Q000528:radiation effects; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D054833:Isoindoles; D010860:Pigments, Biological / Q000138:chemical synthesis* / Q000494:pharmacology; D011838:Radiation-Sensitizing Agents / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D007211:Indoles; D054833:Isoindoles; D010860:Pigments, Biological; D011838:Radiation-Sensitizing Agents; C013647:phthalocyanine