TY - JOUR

T1 - N,O-bidentate ligands-based salicylic spiroborates: A bright frontier of bioimaging

AU - Lugovik, Kseniya I.

AU - Fomin, Timur O.

AU - Minin, Artem S.

AU - Pozdina, Varvara A.

AU - Shevyrin, Vadim A.

AU - Benassi, Enrico

AU - Belskaya, Nataliya P.

N1 - Funding Information: We thank Russian Science Foundation for financially supporting this work through project 20-13-00089. This work was performed using the equipment of the Shared Research Center of Scientific Equipment SRC IIP UrB RAS. We also gratefully acknowledge the Siberian Branch of the Russian Academy of Sciences (SB RAS) Siberian Supercomputer Centre for providing supercomputer facilities. Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/4

Y1 - 2022/4

N2 - A new series of salicylic spiroborate complexes (SSBs) based on N,O-bidentate 2-(tert-cycloalkylamino)-5-(3-(arylamino)acryloyl)thiophene-3-carbonitriles (NO-SSBs) was obtained and characterized. The optical properties of these compounds were studied and compared with those of analogous BF2-based complexes. The geometries and electronic structures of the NO-SSBs in the ground and excited states, especially their key N–B–O link, were revealed using quantum chemical calculations and compared with the experimental data and photophysical characteristics. Hydrolytic dissociation and photodissociation were considered, and the effects of the NO-SSB structure and nature of the solvent on these reactions were established. Biological investigations elucidated the NO-SSBs ability to penetrate living and fixed cells and selectively accumulate in the endoplasmic reticulum (ER) and Golgi complex. Comparison of the NO-SSBs’ characteristics with those of a commercial dye demonstrated the superiority of their properties and prospects for application in the bio-visualization of the ER and Golgi complex.

AB - A new series of salicylic spiroborate complexes (SSBs) based on N,O-bidentate 2-(tert-cycloalkylamino)-5-(3-(arylamino)acryloyl)thiophene-3-carbonitriles (NO-SSBs) was obtained and characterized. The optical properties of these compounds were studied and compared with those of analogous BF2-based complexes. The geometries and electronic structures of the NO-SSBs in the ground and excited states, especially their key N–B–O link, were revealed using quantum chemical calculations and compared with the experimental data and photophysical characteristics. Hydrolytic dissociation and photodissociation were considered, and the effects of the NO-SSB structure and nature of the solvent on these reactions were established. Biological investigations elucidated the NO-SSBs ability to penetrate living and fixed cells and selectively accumulate in the endoplasmic reticulum (ER) and Golgi complex. Comparison of the NO-SSBs’ characteristics with those of a commercial dye demonstrated the superiority of their properties and prospects for application in the bio-visualization of the ER and Golgi complex.

KW - (TD)DFT

KW - Bioimaging

KW - Fluorescence

KW - N,O-bidentate ligand

KW - Salicylic spiroborates

UR - http://www.scopus.com/inward/record.url?scp=85124987218&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/6c8122e7-813b-3c39-baf3-097ac454799e/

U2 - 10.1016/j.dyepig.2022.110165

DO - 10.1016/j.dyepig.2022.110165

M3 - Article

AN - SCOPUS:85124987218

VL - 200

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 110165

ER -