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

Petr V. Ostroverkhov,^a@ Nikita S. Kirin,^a Sergey I. Tikhonov,^a Maxim N. Usachev,^a Olga B. Abramova,^bMikhail A. Kaplan,^bAndrey F. Mironov ^a and Mikhail A. Grin^a

^aMIREA – Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies), 119571 Moscow, Russia

^bA. Tsyb Medical Radiological Research Center – branch of the National Medical Research Radiological Center of the Ministry of Health of the Russian Federation (A. Tsyb MRRC), 249031 Obninsk, Kaluga region, Russia

^@Corresponding author E-mail: ostroverhov@mirea.ru

DOI: 10.6060/mhc224071o
Macroheterocycles 2021 14(4) 270-279

Dedicated to the memory of Prof. A. F. Mironov, and Prof. G. V. Ponomarev

Targeted molecular therapy is one of the approaches in the pharmacotherapy of cancer. 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 e₆ 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.

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

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