Synthesis of positively charged phthalocyanines and their activity in the photodynamic therapy of cancer cells.
Positively charged zinc containing or metal free phthalocyanines 6a-c and 7a-c were prepared via a three step procedure starting from 4-nitrophthalonitrile. The phthalocyanines contain alkyl chains of different length in order to influence the hydrophilic vs lipophilic character of the compounds. The partition between a hydrophilic (water) and lipophilic (octanol-1) phase was determined, and the photoredox activities were investigated. Initial results on the photodynamic activity of these compounds were compared with those of Dougherty's Photofrin II on different malignant and non-malignant cell lines (XP 29MAmal, CX1, HeLa, S180 and NO17). Positively charged phthalocyanines in vitro showed a higher photodynamic activity than Photofrin II.
Wöhrle
D
D
Institut für Organische und Makromolekulare Chemie, Universität Bremen, W. Germany.
Iskander
N
N
Graschew
G
G
Sinn
H
H
Friedrich
E A
EA
Maier-Borst
W
W
Stern
J
J
Schlag
P
P
D000818:Animals; D002470:Cell Survival / Q000187:drug effects*; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D054833:Isoindoles; D010778:Photochemotherapy; D011838:Radiation-Sensitizing Agents / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects*
D007211:Indoles; D054833:Isoindoles; D011838:Radiation-Sensitizing Agents; C013647:phthalocyanine