AIE-active Cyclen-BODIPYs as multiresponsive fluorescent probes for imaging in biological samples: Design and comprehensive study

AIE-active Cyclen-BODIPYs as multiresponsive fluorescent probes for imaging in biological samples: Design and comprehensive study Full article

Journal

Talanta
ISSN: 0039-9140 , E-ISSN: 1873-3573

Output data

Year: 2025, Volume: 295, Article number : 128283, Pages count : DOI: 10.1016/j.talanta.2025.128283

Authors

Uvarov Denis Y ¹ , Sapoletova Nina A ² , Kushnir Sergey E ² , Selektor Sofiya L ³ , Golovanov Ivan S ¹ , Chursin Anatoly Y ¹ , Scherbakov Alexander M ^4,5 , Salnikova Diana I ^1,4 , Kopnin Pavel B ⁴ , Kolotyrkina Natalya G ¹ , Fakhrutdinov Artem ¹ , Malakhova Victoria ¹ , Sibgatullina Guzel ⁶ , Samigullin Dmitry ^6,7 , Zavarzin Igor V ¹ , Goze Christine ⁸ , Denat Franck ⁸ , Volkova Yulia A ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russia
2	Department of Chemistry, Lomonosov Moscow State University, 119991, Moscow, Russia.
3	A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31 Bld. 4 Leninsky prosp, 119071, Moscow, Russia.
4	N. N. Blokhin National Medical Research Center of Oncology, 24 Kashirskoe shosse, 115522, Moscow, Russia
5	Gause Institute of New Antibiotics, 11 ul. Bol'shaya Pirogovskaya, 119021, Moscow, Russia.
6	Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center, Russian Academy of Sciences, P.O. box 261, 420111, Kazan, Russia.
7	Department of Radiophotonics and Microwave Technologies, Kazan National Research Technical University Named after A.N. Tupolev-KAI, 10 K. Marx St., 420111, Kazan, Russia
8	Univ. Bourgogne Europe, Institut de Chimie Moléculaire de l'Université de Bourgogne, ICMUB, UMR CNRS 6302, 9 avenue Alain Savary, 21078, Dijon, France

The aggregation-induced emission (AIE) effect opens up new opportunities and prospects for the development of organic light-emitting materials. By exploiting the intrinsic ability of boron-dipyrromethenes (BODIPYs) to form aggregates, we rationally designed water-soluble AIE-active dyes derived from BODIPY fluorophores by their modification with azamacrocyclic units. The most AIE-active cyclen-BODIPY derivatives 5a and 8a showed high fluorescence quantum yields and they were found to be sensitive to water content, viscosity, pH, and temperature with a “turn-on” fluorescence response. The DLS and SEM results showed that these compounds exist as nanoscale aggregates in aqueous solutions. A possible molecular arrangement of dye 5a in aggregates was rationalized using TD-DFT calculations. The biologically relevant metal ions, such as Li+, K+, Na+, and Mg2+, have no pronounced effect on absorption and emission spectra of the dyes 5a and 8a. In vitro confocal microscopy studies in HeLa cells demonstrated that dyes 5a and 8a successfully permeated the cell membrane and selectively labeled lysosomes. These findings suggest that cyclen-BODIPY derivatives hold promise for investigating lysosomal dynamics and function in living cells via fluorescence imaging.

Uvarov D.Y. , Sapoletova N.A. , Kushnir S.E. , Selektor S.L. , Golovanov I.S. , Chursin A.Y. , Scherbakov A.M. , Salnikova D.I. , Kopnin P.B. , Kolotyrkina N.G. , Fakhrutdinov A. , Malakhova V. , Sibgatullina G. , Samigullin D. , Zavarzin I.V. , Goze C. , Denat F. , Volkova Y.A.
AIE-active Cyclen-BODIPYs as multiresponsive fluorescent probes for imaging in biological samples: Design and comprehensive study
Talanta. 2025. V.295. 128283 . DOI: 10.1016/j.talanta.2025.128283 WOS Scopus OpenAlex

≡ Web of science:	WOS:001493649900005
≡ Scopus:	2-s2.0-105004926271
≡ OpenAlex:	W4410104697