Abstract
The review is devoted to methods of targeted chemical modifications of bacteriochlorophyll a. These methods provide an approach to the synthesis of derivatives with improved photophysical properties and increased hydrophilicity and are suited to the design of conjugates with other biologically active molecules utilized for fluorescence diagnosis and binary cancer therapy.
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References
R. K. Pandey, G. Zheng, Porphyrins as Photosensitizers in Photodynamic Therapy, Eds K. M. Kadish, K. M. Smith, R. Guilard, The Porphyrin Handbook, 2000, 157.
N. V. Koudinova, J. H. Pinthus, A. Brandis, O. Brenner, P. Bendel, J. Ramon, Z. Eshhar, A. Scherz, Y. Salomon, Int. J. Cancer, 2003, 104, 782.
M. Ethirajan, Y. Chen, P. Joshi, R. K. Pandey, Chem. Soc. Rev., 2011, 40, 340.
M. A. Grin, A. F. Mironov, A. A. Shtil, Anti-Cancer Agents in Medicinal Chemistry, 2008, 8, 683.
M. A. Grin, A. F. Mironov, in Chemical Processes with Participation of Biological and Related Compounds, Eds T. N. Lomova, G. T. Zaikov, Leiden, Boston, Brill, 2008, 5.
U. Eisner, J. Chem. Soc., 1957, 3461.
H. Scheer, Chlorophylls, CRC Press—Boca Raton, Ann Arbor—Boston—London, 1991.
Pat. RF 2144085; Byul. Izobret. [Inventor Bull.], 2000, No. 1 (in Russian).
A. A. Tsygankov, T. V. Laurinavichene, I. N. Gogotov, Biotechnol. Tech., 1994, 8, 575.
A. A. Tsygankov, T. V. Laurinavichene, V. E. Bukatin, I. N. Gogotov, D. O. Hall, Biochem. Microbiol., 1997, 33, 485.
Zayavka na izobretenie [Application for an Invention] RU 2012144680 A; Byul. Izobret. [Inventor Bull.], 2014, No. 12 (in Russian).
A. F. Mironov, A. N. Kozyrev, A. S. Brandis, Proc. SPIE, 1992, 1922, 204.
E. V. Patrusheva, A. S. Fedorov, V. V. Belera, I. G. Minkevich, A. A. Tsygankov, Prikl. Biokhim. Mikrobiolog. [Appl. Biochem. Microbiol.], 2007, 43, 208 (in Russian).
R. K. Pandey, F.-Y. Shiau, A. B. Sumlin, T. J. Dougherty, K. M. Smith, Bioorg. Med. Chem. Lett., 1994, 4, 1263.
A. N. Kozyrev, G. Zheng, C. F. Zhu, Tetrahedron Lett., 1996, 37, 6431.
A. F. Mironov, M. A. Grin, A. G. Tsiprovskiy, V. V. Kachala, T. A. Karmakova, A. D. Plyutinskaya, R. I. Yakubovskaya, J. Porphyrins Phthalocyanines, 2003, 7, 725.
Pat. RF 2223274; Byul. Izobret. [Inventor Bull.], 2004, No. 4 (in Russian).
Z. Malik, H. Ladan, Y. Nitzan, J. Photochem. Photobiol. B, 1992, 14, 262.
A. Minnock, D. I. Vernon, J. Schofield, J. Griffiths, J. H. Parish, S. T. Brown, J. Photochem. Photobiol. B, 1996, 32, 159.
M. R. Hamblin, T. Hasan, Photochem. Photobiol. Sci., 2004, 3, 436.
H. Rohde, M. A. Horstkotte, D. Mack, J. K. M. Knobloch, Coagulase-negative Staphylococci, in Biofilms, Infection, and Antimicrobial Therapy, Eds J. L. Pace, M. E. Rupp, R. G. Finch, CRC Press, New York, 2005, Ch. 7, 109.
M. Wainwright, J. Antimicrob. Chemother., 1998, 42, 13.
Y. C. Cheng, A. Samia, J. D. Meyers, I. Panagopoulos, B. Fei, C. Burda, J. Am. Chem. Soc., 2008, 130, 10643.
Y. Cheng, A. C. Samia, J. Li, M. E. Kenney, A. Resnick, C. Burda, Langmuir, 2009, 26, 2248.
Y. Cheng, J. D. Meyers, A.-M. Broome, M. E. Kenney, J. P. Basilion, C. Burda, J. Am. Chem. Soc., 2011, 133, 2583.
A. Srivatsan, S. V. Jenkins, M. Jeon, Z. Wu, C. Kim, J. Chen, R. K. Pandey, Theranostics, 2014, 4, 163.
A. J. Mieszawska, W. J. M. Mulder, Z. A. Fayad, D. P. Cormode, Mol. Pharmaceutics, 2013, 10, 831.
D. Peer, J. M. Karp, S. Hong, O. C. Farokhzad, R. Margalit, R. Langer, Nat. Nanotech., 2007, 2, 751.
P. Ghosh, G. Han, M. De, C. K. Kim, V. M. Rotello, Adv. Drug Delivery Rev., 2008, 60, 1307.
S. Rana, A. Bajaj, R. Mout, V. M. Rotello, Adv. Drug Delivery Rev., 2012, 64, 200.
P. A. Panchenko, A. N. Sergeeva, O. A. Fedorova, Y. V. Fedorov, М. A. Grin, R. I. Reshetnikov, A. E. Schelkunova, A. F. Mironov, G. Jonusauskas, J. Photochem. Photobiol. B, 2014, 133, 140.
M. P. A. Williams, M. Ethirajan, K. Ohkubo, P. Chen, P. Pera, J. Morgan, W. H. White, M. Shibata, S. Fukuzumi, K. M. Kadish, R. K. Pandey, Bioconjugate Chem., 2011, 22, 2283.
A. F. Mironov, M. A. Grin, J. Porphyrins Phthalocyanines, 2008, 12, 1163.
M. A. Grin, D. I. Brittal, A. G. Tsiprovskiy, V. I. Bregadze, A. F. Mironov, Macroheterocycles, 2010, 3, 222.
M. A. Grin, A. A. Semioshkin, R. A. Titeev, E. A. Nizhnik, J. N. Grebenyuk, A. F. Mironov, V. I. Bregadze, Mendeleev Commun., 2007, 17, 14.
M. A. Grin, R. A. Titeev, O. M. Bakieva, D. I. Brittal, I. A. Lobanova, I. B. Sivaev, V. I. Bregadze, A. F. Mironov, Russ. Chem. Bull. (Int. Ed.), 2008, 57, 2230 [Izv. Akad. Nauk, Ser. Khim., 2008, 2188].
V. I. Bregadze, I. B. Sivaev, I. A. Lobanova, R. A. Titeev, D. I. Brittal, M. A. Grin, A. F. Mironov, Appl. Radiation Isotopes, 2009, 67, 101.
M. A. Grin, I. S. Lonin, A. A. Lakhina, E. S. Ol´shanskaya, A. I. Makarov, Y. L. Sebyakin, L. Yu. Guryeva, P. V. Toukach, A. S. Kononikhin, V. A. Kuzmin, A. F. Mironov, J. Porphyrins Phthalocyanines, 2009, 13, 336.
M. A. Grin, I. S. Lonin, L. M. Likhosherstov, O. S. Novikova, A. D. Plyutinskaya, E. A. Plotnikova, V. V. Kachala, R. I. Yakubovskaya, A. F. Mironov, J. Porphyrins Phthalocyanines, 2012, 16, 1094.
M. A. Grin, I. S. Lonin, A. I. Makarov, A. A. Lakhina, F. V. Toukach, V. V. Kachala, A. V. Orlova, A. F. Mironov, Mendeleev Commun., 2008, 18, 135.
A. V. Akimova, G. V. Golovina, T. A. Kokrashvili, A. M. Vinogradov, M. A. Grin, A. F. Mironov, G. N. Rychkov, A. A. Shtil´, V. A. Kuz´min, N. A. Durandin, Dokl. AN, 2014, 454, 473 [Dokl. Chem. (Engl. Transl.), 2014, 454].
I. G. Meerovich, M. A. Grin, A. G. Tsyprovskiy, G. A. Meerovich, S. V. Barkanova, L. M. Borisova, N. A. Oborotova, A. Yu. Baryshnikov, A. F. Mironov, Proc. SPIE, 2007, 6427, 64270W1.
B. W. Henderson, A. B. Sumlin, B. L. Owcharczak, T. J. Dougherty, Photochem. Photobiol. B, 1991, 10, 303.
A. Brandis, O. Mazor, E. Neumark, V. Rozenbach-Belkin, Y. Salomon, A. Scherz, Photochem. Photobiol., 2005, 81, 983.
R. K. Pandey, A. B. Sumlin, S. Constantine, M. Aoudia, W. R. Potter, D. A. Bellnier, B. W. Henderson, M. A. Rodgers, K. M. Smith, T. J. Dougherty, Photochem. Photobiol., 1996, 64, 194.
Pat. RF 2411943; Byul. Izobret. [Inventor Bull.], 2011, No. 5 (in Russian).
I. V. Pantyushenko, M. A. Grin, R. I. Yakubovskaya, E. A. Plotnikova, N. B. Morozova, A. A. Tsygankov, A. F. Mironov, Vestn. MITKhT [Bull. Lomonosov Moscow State Academy of Fine Chemical Technology], 2014, 9, 3 (in Russian).
Pat. RF 2521327; Byul. Izobret. [Inventor Bull.], 2014, No. 18 (in Russian).
V. G. Granik, Osnovy meditsinskoi khimii [Fundamentals of Medical Chemistry], 2nd ed., Vuzovskaya kniga, Moscow, 2006, 384 pp. (in Russian).
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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0333—0349, February, 2016.
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Grin, M.A., Mironov, A.F. Chemical transformations of bacteriochlorophyll a and its medical applications. Russ Chem Bull 65, 333–349 (2016). https://doi.org/10.1007/s11172-016-1307-1
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DOI: https://doi.org/10.1007/s11172-016-1307-1