TY - JOUR

T1 - Photophysics, photochemistry and bioimaging application of 8-azapurine derivatives

AU - Eltyshev, Alexander K.

AU - Agafonova, Irina A.

AU - Minin, Artem S.

AU - Pozdina, Varvara A.

AU - Shevirin, Vadim A.

AU - Slepukhin, Pavel 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: © The Royal Society of Chemistry.

PY - 2021/12/7

Y1 - 2021/12/7

N2 - New 2-aryl-1,2,3-triazolopyrimidines were designed, synthesized, and characterized. Their optical properties were thoroughly studied in the solid phase, in solution and in a biological environment. Density Functional Theory (DFT) based calculations were performed, including the molecular geometry optimization for both the ground state and the first singlet excited state, the prediction of the UV-Vis absorption and fluorescence spectra, the determination of the molecular electrostatic properties and the solvent effect on the optical properties. The emission intensity was revealed to increase in time upon irradiation. Mass spectrometric research, quantum mechanical calculations, and analysis of literature data suggested a possible photo-transformation pathway through the homolytic cleavage of one of the C-Cl bonds upon irradiation with UV light. The structure of the active intermediate was identified by the series of mass spectrometry experiments and via synthesis of putative transformation products. The kinetic parameters measured in different solvents allowed estimating the rate of these photo-transformations. Biological experiments demonstrated that 2-aryl-1,2,3-triazolopyrimidines penetrate cells and selectively accumulate in the cell membrane and the Golgi complex and endoplasmic reticulum. Their unique properties pave the way for new possible applications of fluorescent 8-azapurines in biology and medicine. This journal is

AB - New 2-aryl-1,2,3-triazolopyrimidines were designed, synthesized, and characterized. Their optical properties were thoroughly studied in the solid phase, in solution and in a biological environment. Density Functional Theory (DFT) based calculations were performed, including the molecular geometry optimization for both the ground state and the first singlet excited state, the prediction of the UV-Vis absorption and fluorescence spectra, the determination of the molecular electrostatic properties and the solvent effect on the optical properties. The emission intensity was revealed to increase in time upon irradiation. Mass spectrometric research, quantum mechanical calculations, and analysis of literature data suggested a possible photo-transformation pathway through the homolytic cleavage of one of the C-Cl bonds upon irradiation with UV light. The structure of the active intermediate was identified by the series of mass spectrometry experiments and via synthesis of putative transformation products. The kinetic parameters measured in different solvents allowed estimating the rate of these photo-transformations. Biological experiments demonstrated that 2-aryl-1,2,3-triazolopyrimidines penetrate cells and selectively accumulate in the cell membrane and the Golgi complex and endoplasmic reticulum. Their unique properties pave the way for new possible applications of fluorescent 8-azapurines in biology and medicine. This journal is

KW - GOLGI-APPARATUS

KW - PENCLOMEDINE

KW - PROBE

KW - TRICHLOROMETHYL

KW - METABOLITE

KW - BARBAMIDE

KW - NATURES

UR - http://www.scopus.com/inward/record.url?scp=85120372998&partnerID=8YFLogxK

U2 - 10.1039/d1ob01801a

DO - 10.1039/d1ob01801a

M3 - Article

C2 - 34734607

VL - 19

SP - 9880

EP - 9896

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 45

ER -