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Effect of Substituents on Photochemical and Biological Properties of 13,15-N-Cycloimide Derivatives of Chlorin p6

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Abstract

The effect of electron-accepting substituents in position 3 of the chlorine p6 macrocycle in neutral and carboxyl-containing negatively charged cycloimide derivatives of chlorin p6 (CIC) on the photochemical and biological properties of these photosensitizers was studied. The relationship between the structure and properties of CICs was analyzed on the basis of information on their photoinduced cytotoxicity, efficiency of generation of reactive oxygen species, photostability, intracellular localization, quantitative parameters of accumulation in cells, and cellular pharmakinetics. It was shown that these compounds can be used for the development of photosensitizers with intense light absorption at 740 nm, controlled intracellular localization, and a high photodynamic activity toward tumor cells.

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Abbreviations

CIC:

cycloimide derivative of chlorin p6

COMIRSI:

confocal microscopy and reconstruction of spectral images

CrEL:

cremophor EL

DMPC:

dimyristoyl phosphatidylcholine

ER:

endoplasmic reticulum

FCS:

fetal calf serum

NBT:

Nitro Blue Tetrazolium

O ·−2 :

superoxide ion

PDT:

photodynamic therapy

PS:

photosensitizer

ROS:

reactive oxygen species

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Authors and Affiliations

  1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia

    A. I. Nazarova, A. V. Feofanov & G. V. Sharonov

  2. Herzen Oncological Research Institute, Moscow, Russia

    T. A. Karmakova, A. D. Plyutinskaya & R. I. Yakubovskaya

  3. Lomonosov State Academy of Fine Chemical Technology, pr. Vernadskogo 86, Moscow, 117571, Russia

    V. S. Lebedeva & A. F. Mironov

  4. Centre de Biophysique Moleculaire, CNRS, Orleans, France

    J.-C. Maurizot & P. Vigny

Authors
  1. A. I. Nazarova
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  2. A. V. Feofanov
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  3. T. A. Karmakova
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  4. G. V. Sharonov
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  5. A. D. Plyutinskaya
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  6. R. I. Yakubovskaya
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  7. V. S. Lebedeva
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  8. A. F. Mironov
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  9. J.-C. Maurizot
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  10. P. Vigny
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Corresponding author

Correspondence to A. V. Feofanov.

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__________

Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 5, 2005, pp. 535–548.

Original Russian Text Copyright © 2005 by Nazarova, Feofanov, Karmakova, Sharonov, Plyutinskaya, Yakubovskaya, Lebedeva, Mironov, Maurizot, Vigny.

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Nazarova, A.I., Feofanov, A.V., Karmakova, T.A. et al. Effect of Substituents on Photochemical and Biological Properties of 13,15-N-Cycloimide Derivatives of Chlorin p6. Russ J Bioorg Chem 31, 482–494 (2005). https://doi.org/10.1007/s11171-005-0066-9

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  • DOI: https://doi.org/10.1007/s11171-005-0066-9

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