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Molecules, volume 28, issue 9, pages 3866

Novel Indoline Spiropyrans Based on Human Hormones β-Estradiol and Estrone: Synthesis, Structure, Chromogenic and Cytotoxic Properties

Ozhogin Ilya V ¹

Pugachev Artem D ¹

Makarova Nadezhda I ¹

Belanova Anna A. ²

Kozlenko Anastasia S ¹

Rostovtseva Irina A ¹

Zolotukhin Peter V ²

Demidov Oleg P ³

El-Sewify Islam M. ⁴

Borodkin Gennady S ¹

Metelitsa Anatoly V. ¹

Lukyanov Boris S ¹

Hide authors affiliations Show authors affiliations: 4 affiliations

Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090 Rostov-on-Don, Russia |

Academy of Biology and Biotechnology, Southern Federal University, 194/1 Stachka Ave., 344090 Rostov-on-Don, Russia |

Faculty of Chemistry and Pharmacy, North-Caucasus Federal University, 1 Pushkina Str., 355000 Stavropol, Russia |

⁴

Department of Chemistry, Faculty of Science, Ain shams University, Cairo 11566, Egypt |

Publication type: Journal Article

Publication date: 2023-05-04

Multidisciplinary Digital Publishing Institute (MDPI)

Journal: Molecules

Quartile SCImago

Quartile WOS

Impact factor: 4.6

ISSN: 14203049

DOI: 10.3390/molecules28093866

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PubMed ID: 37175276

Organic Chemistry

Drug Discovery

Physical and Theoretical Chemistry

Pharmaceutical Science

Molecular Medicine

Analytical Chemistry

Chemistry (miscellaneous)

Abstract

The introduction of a switchable function into the structure of a bioactive compound can endow it with unique capabilities for regulating biological activity under the influence of various types of external stimuli, which makes such hybrid compounds promising objects for photopharmacology, targeted drug delivery and bio-imaging. This work is devoted to the synthesis and study of new spirocyclic derivatives of important human hormones—β-estradiol and estrone—possessing a wide range of biological activities. The obtained hybrid compounds represent an indoline spiropyrans family, a widely known class of organic photochromic compounds. The structure of the compounds was confirmed by 1H and 13C NMR, IR, HRMS and single-crystal X-ray analysis. The intermolecular interactions in the crystals of spiropyran (3) were defined by Hirshfeld surfaces and 2D fingerprint plots, which were successfully acquired from CrystalExplorer (v21.5). All target hybrids demonstrated pronounced activity in the visible region of the spectrum. The mechanisms of thermal isomerization processes of spiropyrans and their protonated merocyanine forms were studied by DFT methods, which revealed the energetic advantage of the protonation process with the formation of a β-cisoid CCCH conformer at the first stage and its further isomerization to more stable β-transoid forms. The proposed mechanism of acidochromic transformation was confirmed by the additional NMR study data that allowed for the detecting of the intermediate CCCH isomer. The study of the short-term cytotoxicity of new spirocyclic derivatives of estrogens and their 2-formyl-precursors was performed on the HeLa cell model. The precursors and spiropyrans differed in toxicity, suggesting their variable applicability in novel anti-cancer technologies.

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Ozhogin I. V. et al. Novel Indoline Spiropyrans Based on Human Hormones β-Estradiol and Estrone: Synthesis, Structure, Chromogenic and Cytotoxic Properties // Molecules. 2023. Vol. 28. No. 9. p. 3866.

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Ozhogin I. V., Pugachev A. D., Makarova N. I., Belanova A. A., Kozlenko A. S., Rostovtseva I. A., Zolotukhin P. V., Demidov O. P., El-Sewify I. M., Borodkin G. S., Metelitsa A. V., Lukyanov B. S. Novel Indoline Spiropyrans Based on Human Hormones β-Estradiol and Estrone: Synthesis, Structure, Chromogenic and Cytotoxic Properties // Molecules. 2023. Vol. 28. No. 9. p. 3866.

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TY - JOUR

DO - 10.3390/molecules28093866

UR - https://doi.org/10.3390%2Fmolecules28093866

TI - Novel Indoline Spiropyrans Based on Human Hormones β-Estradiol and Estrone: Synthesis, Structure, Chromogenic and Cytotoxic Properties

T2 - Molecules

AU - Ozhogin, Ilya V

AU - Pugachev, Artem D

AU - Makarova, Nadezhda I

AU - Belanova, Anna A.

AU - Kozlenko, Anastasia S

AU - Rostovtseva, Irina A

AU - Zolotukhin, Peter V

AU - Demidov, Oleg P

AU - El-Sewify, Islam M.

AU - Borodkin, Gennady S

AU - Metelitsa, Anatoly V.

AU - Lukyanov, Boris S

PY - 2023

DA - 2023/05/04 00:00:00

PB - Multidisciplinary Digital Publishing Institute (MDPI)

SP - 3866

IS - 9

VL - 28

PMID - 37175276

SN - 1420-3049

ER -

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@article{2023_Ozhogin,

author = {Ilya V Ozhogin and Artem D Pugachev and Nadezhda I Makarova and Anna A. Belanova and Anastasia S Kozlenko and Irina A Rostovtseva and Peter V Zolotukhin and Oleg P Demidov and Islam M. El-Sewify and Gennady S Borodkin and Anatoly V. Metelitsa and Boris S Lukyanov},

title = {Novel Indoline Spiropyrans Based on Human Hormones β-Estradiol and Estrone: Synthesis, Structure, Chromogenic and Cytotoxic Properties},

journal = {Molecules},

year = {2023},

volume = {28},

publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},

month = {may},

url = {https://doi.org/10.3390%2Fmolecules28093866},

number = {9},

pages = {3866},

doi = {10.3390/molecules28093866}

}

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Ozhogin, Ilya V., et al. “Novel Indoline Spiropyrans Based on Human Hormones β-Estradiol and Estrone: Synthesis, Structure, Chromogenic and Cytotoxic Properties.” Molecules, vol. 28, no. 9, May. 2023, p. 3866. https://doi.org/10.3390%2Fmolecules28093866.

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