Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry

Kseniya I. Lugovik, Alexander K. Eltyshev, Polina O. Suntsova, Leonid T. Smoluk, Anna V. Belousova, Maria V. Ulitko, Artem S. Minin, Pavel A. Slepukhin, Enrico Benassi, Nataliya P. Belskaya

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

This study presents the synthesis and optical properties of a new class of bright green-yellow fluorescent dyes with potential applications in bioimaging. A facile synthetic route via the chelation of aryl(hetaryl)aminoacryloylthiophene scaffolds with a BF2 fragment is presented. The photophysical properties of the dyes are attributed to the nature and position of electron-donating and electron-withdrawing substituents. Upon coordination to a BF2 fragment, characteristic emission was observed, with λem ranging from 503 to 543 nm and quantum yields of 0.14-0.42. Compared with parent aryl(hetaryl)aminoacryloylthiophenes, a significant red shift in absorption (up to 480 nm in solution) and emission (up to 543 nm in solution and 610 nm in the solid state) and high chemical stability and photostability were observed. The electron-accepting character of the substituents on the terminal aromatic ring or replacing this fragment with pyridine or pyrazine moieties resulted in increased quantum yields. To gain insight into the electronic structures and optical properties, quantum mechanical calculations were performed. The results of (TD-)DFT calculations supported the structural and spectroscopic data and showed the features of electronic distribution in the frontier molecular orbitals and active electrophilic and nucleophilic sites in the compounds investigated. Synthesized BF2 complexes are promising dyes for cell imaging and flow cytometry owing to their ready penetration and accumulation in cells.

Original languageEnglish
Pages (from-to)5150-5162
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number28
DOIs
Publication statusPublished - 1 Jan 2018
Externally publishedYes

Fingerprint

Boron
cytometry
Flow cytometry
chelates
Flow Cytometry
boron
dyes
fragments
Quantum yield
Electrons
Coloring Agents
Optical properties
Pyrazines
optical properties
chelation
electrons
pyrazines
Chemical stability
Molecular orbitals
Chelation

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Lugovik, K. I., Eltyshev, A. K., Suntsova, P. O., Smoluk, L. T., Belousova, A. V., Ulitko, M. V., ... Belskaya, N. P. (2018). Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry. Organic and Biomolecular Chemistry, 16(28), 5150-5162. https://doi.org/10.1039/c8ob00868j

Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry. / Lugovik, Kseniya I.; Eltyshev, Alexander K.; Suntsova, Polina O.; Smoluk, Leonid T.; Belousova, Anna V.; Ulitko, Maria V.; Minin, Artem S.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 28, 01.01.2018, p. 5150-5162.

Research output: Contribution to journalArticle

Lugovik, KI, Eltyshev, AK, Suntsova, PO, Smoluk, LT, Belousova, AV, Ulitko, MV, Minin, AS, Slepukhin, PA, Benassi, E & Belskaya, NP 2018, 'Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry', Organic and Biomolecular Chemistry, vol. 16, no. 28, pp. 5150-5162. https://doi.org/10.1039/c8ob00868j
Lugovik KI, Eltyshev AK, Suntsova PO, Smoluk LT, Belousova AV, Ulitko MV et al. Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry. Organic and Biomolecular Chemistry. 2018 Jan 1;16(28):5150-5162. https://doi.org/10.1039/c8ob00868j
Lugovik, Kseniya I. ; Eltyshev, Alexander K. ; Suntsova, Polina O. ; Smoluk, Leonid T. ; Belousova, Anna V. ; Ulitko, Maria V. ; Minin, Artem S. ; Slepukhin, Pavel A. ; Benassi, Enrico ; Belskaya, Nataliya P. / Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 28. pp. 5150-5162.
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