BACTERIOCHLORIN-CONTAINING TRIAD: STRUCTURE AND PHOTOPHYSICAL PROPERTIES

M.A. Grin^a, Ph.V. Toukach^b, V.B. Tsvetkov^d,e, R.I. Reshetnikov^a, O.V. Kharitonova^a, A.S. Kozlov^c, A.A. Krasnovsky Jr.^c, A.F. Mironov^a

^aM.V. Lomonosov Academy of Fine Chemical Technology, Moscow, Russia
^bN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
^cA.N. Bach Institute of Biochemistry, Russian Academy of Sciences, Moscow, Russia
^dA.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russia
^eInstitute for Physical-Chemical Medicine, Moscow, Russia

Dyes and Pigments, 2015, v.121, pp. 21-29

DOI: 10.1016/j.dyepig.2015.04.034

A new theranostic agent of bacteriochlorin family has been synthesized by the reaction between 13¹-(2-aminoethylcarbamoyl)bacteriochlorin e and N,N’-di(carboxypentyl)dicarboindocyanine dye. The structure of the synthesized conjugate was confirmed by nuclear-magnetic resonance spectroscopy. In the conjugate, the efficient energy transfer from the dye to bacteriochlorin was observed. The yield of this process, which was shown to be ~94%, allowed the dye still retain its ability to fluoresce. Accordingly, the fluorescence spectrum contained two major bands corresponding to fluorescence of bacteriochlorin (756 nm) and conjugated dye (672 nm). It was observed that the conjugate efficiently photosensitizes formation of singlet oxygen and photodynamic oxygenation of an organic compound. The data suggest that the obtained synthetic conjugate is promising for application in both fluorescence diagnostics and photodynamic treatment of tumors.

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