Targetable Photoactivatable Drugs. 1. Synthesis Of Water-Soluble Galactosamine . Containing Polymeric Carriers Of Chlorin E6 And Their Photodynamic Effect On Plc Cells In Vitro

N. L. Krinick; B. Rihova; K. Ulbrich; J. D. Andrade; J. D. Andrade; J. Kopecek

doi:10.1117/12.960187

17 March 1989 Targetable Photoactivatable Drugs. 1. Synthesis Of Water-Soluble Galactosamine . Containing Polymeric Carriers Of Chlorin E6 And Their Photodynamic Effect On Plc Cells In Vitro

N. L. Krinick, B. Rihova, K. Ulbrich, J. D. Andrade, J. D. Andrade, J. Kopecek

Author Affiliations +

Proceedings Volume 0997, Advances in Photochemotherapy; (1989) https://doi.org/10.1117/12.960187
Event: O-E/Fiber LASE '88, 1988, Boston, MA, United States

Abstract

A copolymer of N-(2-hydroxypropyl)methacrylamide (HPMA) and N-methacryloylglycine p-nitrophenyl ester (MA-Gly-ONp) was synthesized by radical precipitation copolymerization. Galactosamine was coupled to the polymer by reaction with the active ester side chains. The remaining p-nitrophenyl groups were converted to amine functionalities via a polymeranalogous reaction with an excess of ethylene diamine. Chlorin e6 was activated using a mixed anhydride method and subsequently bound to the modified side chains of the polymer. The photodynamic activity of the conjugate with galactosamine as the targeting moiety was tested in vitro on a human hepatoma cell line: PLC/PRF/5 (Alexander cells). It appears that the conjugate enters the cell interior by receptor mediated pinocytosis via the asialoglycoprotein receptors present on the surface of the PLC cells. Photoactivation of the chlorin containing conjugate with red light proved cytotoxic to the cells. Structure tests comparing the HPMA copolymer-galactosamine-chlorin e6 conjugate and a nontargetable HPMA copolymer-chlorin e6 conjugate, with comparable chlorin e6 content, indicate that the targeted conjugate is more biologically active.

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N. L. Krinick, B. Rihova, K. Ulbrich, J. D. Andrade, J. D. Andrade, and J. Kopecek "Targetable Photoactivatable Drugs. 1. Synthesis Of Water-Soluble Galactosamine . Containing Polymeric Carriers Of Chlorin E6 And Their Photodynamic Effect On Plc Cells In Vitro", Proc. SPIE 0997, Advances in Photochemotherapy, (17 March 1989); https://doi.org/10.1117/12.960187

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