Synthesis and Investigation of Photophysical and Biological Properties of Novel S-Containing Bacteriopurpurinimides.
Andrey F Mironov
1
,
Mikhail A. Grin
1
,
Ivan V Pantushenko
1
,
Yan Ivanenkov
2, 3
,
Gleb I. Filkov
4
,
Ekaterina A. Plotnikova
5
,
Tatyana A. Karmakova
5
,
Anna V Starovoitova
6
,
Nelli V Burmistrova
6
,
Vadim V. Yuzhakov
6
,
Yuri S Romanko
6
,
Maxim A. Abakumov
7, 8
,
Anastasiya A Ignatova
9, 10
,
A. V. Feofanov
9, 10
,
Mikhail A Kaplan
6
,
Raisa I. Yakubovskaya
5
,
Anatoliy A. Tsigankov
11
,
Alexander G. Majouga
2, 8
Publication type: Journal Article
Publication date: 2017-12-18
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
29202233
Drug Discovery
Molecular Medicine
Abstract
Novel hybrid molecule containing 2-mercaptoethylamine was synthesized starting from O-propyloxime-N-propoxy bacteriopurpurinimide (dipropoxy-BPI), which was readily oxidized in oxygen atmosphere yielding the corresponding disulfide analogue (disulfide-BPI). Spectral, photophysical, photodynamic, and biological properties of compound were properly evaluated. Compounds bearing disulfide moiety can directly interact with glutathione (GSH), thereby reducing its intracellular concentration. Indeed, mice sarcoma S37 cell line was treated in vitro with disulfide-BPI, yielding a CC50 value of 0.05 ± 0.005 μM. A relatively high level of singlet oxygen was detected. It was demonstrated (by fluorescence) that the PS was rapidly accumulated in a cancer nest (S37) at a relatively high level after 2 h upon intravenous administration. After 24 h, no traces of the molecule were detected in the tumor mass. Moreover, high photodynamic efficiency was demonstrated at doses of 150-300 J/cm2 against two different in vivo tumor models, achieving 100% regression of cancer growth.
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16
Total citations:
16
Citations from 2024:
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(31%)
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Mironov A. F. et al. Synthesis and Investigation of Photophysical and Biological Properties of Novel S-Containing Bacteriopurpurinimides. // Journal of Medicinal Chemistry. 2017. Vol. 60. No. 24. pp. 10220-10230.
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Mironov A. F., Grin M. A., Pantushenko I. V., Ostroverkhov P., Ivanenkov Y., Filkov G. I., Plotnikova E. A., Karmakova T. A., Starovoitova A. V., Burmistrova N. V., Yuzhakov V. V., Romanko Y. S., Abakumov M. A., Ignatova A. A., Feofanov A. V., Kaplan M. A., Yakubovskaya R. I., Tsigankov A. A., Majouga A. G. Synthesis and Investigation of Photophysical and Biological Properties of Novel S-Containing Bacteriopurpurinimides. // Journal of Medicinal Chemistry. 2017. Vol. 60. No. 24. pp. 10220-10230.
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TY - JOUR
DO - 10.1021/acs.jmedchem.7b00577
UR - https://doi.org/10.1021/acs.jmedchem.7b00577
TI - Synthesis and Investigation of Photophysical and Biological Properties of Novel S-Containing Bacteriopurpurinimides.
T2 - Journal of Medicinal Chemistry
AU - Mironov, Andrey F
AU - Grin, Mikhail A.
AU - Pantushenko, Ivan V
AU - Ostroverkhov, Petr
AU - Ivanenkov, Yan
AU - Filkov, Gleb I.
AU - Plotnikova, Ekaterina A.
AU - Karmakova, Tatyana A.
AU - Starovoitova, Anna V
AU - Burmistrova, Nelli V
AU - Yuzhakov, Vadim V.
AU - Romanko, Yuri S
AU - Abakumov, Maxim A.
AU - Ignatova, Anastasiya A
AU - Feofanov, A. V.
AU - Kaplan, Mikhail A
AU - Yakubovskaya, Raisa I.
AU - Tsigankov, Anatoliy A.
AU - Majouga, Alexander G.
PY - 2017
DA - 2017/12/18
PB - American Chemical Society (ACS)
SP - 10220-10230
IS - 24
VL - 60
PMID - 29202233
SN - 0022-2623
SN - 1520-4804
ER -
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@article{2017_Mironov,
author = {Andrey F Mironov and Mikhail A. Grin and Ivan V Pantushenko and Petr Ostroverkhov and Yan Ivanenkov and Gleb I. Filkov and Ekaterina A. Plotnikova and Tatyana A. Karmakova and Anna V Starovoitova and Nelli V Burmistrova and Vadim V. Yuzhakov and Yuri S Romanko and Maxim A. Abakumov and Anastasiya A Ignatova and A. V. Feofanov and Mikhail A Kaplan and Raisa I. Yakubovskaya and Anatoliy A. Tsigankov and Alexander G. Majouga},
title = {Synthesis and Investigation of Photophysical and Biological Properties of Novel S-Containing Bacteriopurpurinimides.},
journal = {Journal of Medicinal Chemistry},
year = {2017},
volume = {60},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.jmedchem.7b00577},
number = {24},
pages = {10220--10230},
doi = {10.1021/acs.jmedchem.7b00577}
}
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MLA
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Mironov, Andrey F., et al. “Synthesis and Investigation of Photophysical and Biological Properties of Novel S-Containing Bacteriopurpurinimides..” Journal of Medicinal Chemistry, vol. 60, no. 24, Dec. 2017, pp. 10220-10230. https://doi.org/10.1021/acs.jmedchem.7b00577.