Guanidine and Biguanidine Derivatives of Natural Chlorins: Synthesis and Biological Assessment

Abstract

The targeted action on the tumor alone does not harm the healthy tissues around the tumor and the overall patient's health, thus eliminating the adverse effects that arise upon chemotherapy or radiation treatment. The targeted delivery of drugs to specific cellular targets to increase the efficiency of drugs is an urgent goal of modern medicinal chemistry. In this work, guanidine and biguanidine groups were incorporated into chlorin e 6 aminoamide in order to create two targeting photosensitizers with high photodynamic efficiency that was proved in in vivo experiments in animals with tumors of various origins (mice Ehrlich carcinoma and rat sarcoma M-1). Optimal methods were suggested for the synthesis of the desired chlorins, which provide high reaction yields under relatively mild conditions. Taking into account the broad capabilities of guanidine and biguanidine derivatives, including heterocyclization, metal chelation, etc., the pigments suggested in this article may be considered as a platform for creating multifunctional photosensitizers of chlorin series.

N-Heterocyclic Carbenes and Their Metal Complexes Based on Histidine and Histamine Derivatives of Bacteriopurpurinimide for the Combined Chemo- and Photodynamic Therapy of Cancer

“…Photosensitizers (PS) based on bacteriochlorophyll a derivatives, in particular, bacteriopurpurinimides (BPI) that absorb radiation in the 800 nm range, are promising agents for photodynamic therapy (PDT), which we are actively studying, including the synthesis of amino acid derivatives of BPI and their metal complexes as agents with combined antitumor action [ 25 , 26 ].…”

“…The first option includes the modification of functional groups or residues of bioactive molecules on the macrocycle periphery. The other approach aims at creating a metal complex of an amino acid followed by binding it to bacteriochlorin [ 26 , 27 , 28 , 29 ].…”