Synthesis and biological investigations of tetrakis(p-carboranylthio-tetrafluorophenyl)chlorin (TPFC).
We describe the total synthesis and biological properties of a new carboranyl-containing chlorin (TPFC) that might find application as a dual sensitizer in the PDT and BNCT treatment of cancer. TPFC was found to be non-toxic in the dark but showed extensive photosensitizing ability both in vitro and in vivo despite its relatively low singlet oxygen quantum yield. In particular, TPFC exhibited significant photosensitizing activity against highly pigmented melanotic melanoma tumors in mice.
Hao
Erhong
E
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
Friso
Elisabetta
E
Miotto
Gianni
G
Jori
Giulio
G
Soncin
Marina
M
Fabris
Clara
C
Sibrian-Vazquez
Martha
M
Vicente
M Graça H
MG
D000818:Animals; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology* / Q000633:toxicity; D016754:Boron Neutron Capture Therapy; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D042541:Intracellular Space / Q000378:metabolism; D051379:Mice; D010777:Photochemistry; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology* / Q000633:toxicity; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology* / Q000633:toxicity
D001896:Boron Compounds; D017319:Photosensitizing Agents; D011166:Porphyrins; C533262:tetrakis(4-carboranylthiotetrafluorophenyl)chlorin; C006969:chlorin