Журнал "Макрогетероциклы"

Mikhail A. Grin,^a@ Dmitry I. Brittal,^a Aleksander G. Tsiprovskiy,^a Vladimir I. Bregadze,^b and Andrey F. Mironov^a

^aM.V. Lomonosov Moscow State Academy of Fine Chemical Technology, 119571 Moscow, Russia

^bA.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119991 Moscow, Russia

^@Corresponding author E-mail: michael_grin@mail.ru

DOI: 10.6060/mhc2010.4.222

Macroheterocycles 2010 3(4) 222-227

Boron neutron capture therapy (BNCT) is binary method for the treatment of cancer, which is based on the nuclear reaction of two essentially nontoxic species, nonradioactive 10B and low energy thermal neutrons. The neutron capture reaction by 10B produces high-linear-energy transfer ions 4He2+ and 7Li+ that dissipate their kinetic energy during traveling one cell diameter (5–9 µm) in biological tissues, giving them the potential for precise cell-killing. Efficient BNCT requires selective accumulation of 10B atoms in cancer cells. Since tetrapyrrole compounds have a unique property of being selectively accumulated in tumor tissues, they have attracted attention as agents for both the targeted delivery of boron clusters to tumor cells and the combined PDT—BNCT therapy, which would undoubtedly enhance the efficiency of antitumor therapy. From this point of view, chlorin based photosensitizers with intense near IR absorption are of particular interest. Chlorins are photosensitizers that have high quantum yields of singlet oxygen production and absorb light in the 640–690 nm region, i.e. within the so-called ‘phototherapeutic window’ (630–900 nm), where light absorption and scattering in human tissues are minimized and they are relatively transparent for activating light. In this contribution we describe the synthesis of conjugates of natural chlorins and bacteriochlorins with closo-dodecaborate and cobaltbis(dicarbollide) anions. In the present work, the Sonogashira reaction, the ‘click’ methodology, which are actively employed in modern organic chemistry were used for the synthesis of boron-containing conjugates of natural chlorins and bacteriochlorins.

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