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Development of Bacteriochlorophyll a-Based Near-Infrared Photosensitizers Conjugated to Gold Nanoparticles for Photodynamic Therapy of Cancer

I. V. Pantiushenko1, P. G. Rudakovskaya2,3, A. V. Starovoytova4, A. A. Mikhaylovskaya4, M. A. Abakumov5, M. A. Kaplan4, A. A. Tsygankov6, A. G. Majouga2,3, M. A. Grin1*, and A. F. Mironov1

1Lomonosov Moscow State University of Fine Chemical Technologies, 119571 Moscow, Russia; E-mail: michael_grin@mail.ru

2Lomonosov Moscow State University, 119991 Moscow, Russia; E-mail: alexander.majouga@gmail.com

3National University of Science and Technology MISiS, 119991 Moscow, Russia

4Cyb Scientific Research Center of Radiology, Hertsen Federal Medical Research Center, Ministry of Health of the Russian Federation, 249036 Obninsk, Kaluga Region, Russia; E-mail: kaplan@mrrc.obninsk.ru

5Pirogov Russian National Research Medical University, Department of Medical Nanobiotechnology, 117997 Moscow, Russia; E-mail: abakumov88@gmail.com

6Institute of Basic Biological Problems, Russian Academy of Sciences, 142290 Pushchino, Moscow Region, Russia; E-mail: ttt-01@rambler.ru

* To whom correspondence should be addressed.

Received February 5, 2015; Revision received March 7, 2015
We report the synthesis and characterization of a new sulfur-containing derivative of bacteriochlorophyll a. The latter was isolated from biomass of the nonsulfur purple bacterium Rhodobacter capsulatus strain B10. The developed photosensitizer is N-aminobacteriopurpurinimide with an exocyclic amino group acylated with a lipoic acid moiety, which is a biogenic substance that acts as a cofactor of the pyruvate dehydrogenase and α-ketoglutarate dehydrogenase complexes in the body. The disulfide moiety of lipoic acid confers the compound aurophilicity, thus allowing its conjugation with gold nanoparticles (NP-Au) via S–Au bonds. The shape and the size of the resulting nanoconjugate with immobilized photosensitizer (PS–Au) were assessed by dynamic light scattering and transmission electron microscopy. The conjugated nanoparticles are spherical with hydrodynamic diameter of 100-110 nm. The PS–Au conjugate absorbs light at 824 nm and emits strong fluorescence at 830 nm, which allowed in vivo study of its dynamic biodistribution in rats bearing sarcoma M-1. Compared to the free photosensitizer, PS loaded on the gold nanoparticles (PS–Au) showed extended circulation time in the blood and enhanced tumor uptake due to nonspecific passive targeting when the drug accumulates in tumor sites through the leaky tumor neovasculature and does not return to the circulation.
KEY WORDS: bacteriochlorophyll a, bacteriopurpurinimide, photosensitizers, photodynamic therapy, lipoic acid, gold nanoparticles, sarcoma M-1

DOI: 10.1134/S0006297915060103