Amino acid functionalized benzanthrone dyes: Synthesis and photophysical study

被引：3

作者：

Konstantinova, Anastasija ^{[1
]}

Avotina, Liga ^{[2
]}

Kizane, Gunta ^{[2
]}

Puckins, Aleksandrs ^{[1
]}

Osipovs, Sergejs ^{[1
]}

Kirilova, Elena ^{[1
]}

机构：

[1] Daugavpils Univ, Inst Life Sci & Technol, Daugavpils, Latvia

[2] Univ Latvia, Inst Chem Phys, Riga, Latvia

来源：

DYES AND PIGMENTS | 2022年 / 204卷

关键词：

Amino acids; Benzanthrone; Synthesis; Fluorescence spectroscopy; FLUORESCENT-PROBE; DERIVATIVES; DESIGN;

D O I：

10.1016/j.dyepig.2022.110363

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The substitution reaction of 3-N-(2-chloroacetamido)benzanthrone with a number of the amino acids is reported. The possibility of using this halogenated benzanthrone for fluorescent labelling of amino acids has been studied. Arginine is the most reactive amino acid in the reaction, as it was found in the study. The spectral behavior of new benzanthrone derivatives depends on the polarity of the medium, exhibiting fluorescent solvatochromism due to intramolecular charge transfer from the substituted amino group to the carbonyl group. The results ob-tained indicate that the synthesized compounds are promising for studying peptides and proteins, as well as for visualizing biological objects.

引用

页数：8

共 47 条

[11] Unnatural benz-X-azolyl asparagine derivatives as novel fluorescent amino acids: synthesis and photophysical characterization [J].

Esteves, Catia I. C. ;

Silva, Ana M. F. ;

Raposo, M. Manuela M. ;

Costa, Susana P. G. .

TETRAHEDRON, 2009, 65 (45) :9373-9377

[12] Synthesis of short and long-wavelength functionalised probes: amino acids' labelling and photophysical studies [J].

Frade, Vania H. J. ;

Barros, Siria A. ;

Moura, Joao C. V. P. ;

Coutinho, Paulo J. G. ;

Goncalves, A. Sameiro T. .

TETRAHEDRON, 2007, 63 (50) :12405-12418

[13] Spectrofluorimetric determination of thiols in biological samples with a new fluorescent probe 3-maleimidylbenzanthrone [J].

Fu, NN ;

Wang, H ;

Li, ML ;

Zheng, GJ ;

Zhang, HS .

ANALYTICAL LETTERS, 2005, 38 (05) :791-802

[14] Phanquinone: a useful fluorescent pre-chromatographic derivatization reagent for liquid chromatographic analyses of amino acid dosage forms [J].

Gatti, R ;

Gioia, MG ;

Di Pietra, AM .

ANALYTICA CHIMICA ACTA, 2002, 474 (1-2) :11-20

[15] A Simple and Rapid Staining Technique for Sex Determination of Trichinella Larvae Parasites by Confocal Laser Scanning Microscopy [J].

Gavarane, Inese ;

Kirilova, Elena ;

Rubenina, Ilze ;

Mezaraupe, Ligita ;

Osipovs, Sergejs ;

Deksne, Gunita ;

Packins, Aleksandrs ;

Kokina, Inese ;

Bulanovs, Andrejs ;

Kirjusina, Muza .

MICROSCOPY AND MICROANALYSIS, 2019, 25 (06) :1491-1497

[16] Dissolution-enhanced emission of 1,3,6,8-Tetrakis(p-benzoic acid)pyrene for detecting arginine and lysine amino acids [J].

Hao, Jinsong ;

Wang, Meng ;

Wang, Shitao ;

Huang, Yan ;

Cao, Dapeng .

DYES AND PIGMENTS, 2020, 175

[17] INTRAMOLECULAR FACILITATED HYDROLYTIC RATES OF METHYL-SUBSTITUTED SUCCINANILIC ACIDS [J].

HIGUCHI, T ;

EBERSON, L ;

HERD, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (16) :3805-&

[18]

Homer R.B., 1970, The Chemistry of Amides, P187

[19] Mini-review: fluorescence imaging in cancer cells using dye-doped nanoparticles [J].

Jenkins, Ragini ;

Burdette, Mary K. ;

Foulger, Stephen H. .

RSC ADVANCES, 2016, 6 (70) :65459-65474

[20] Photophysics of 3-substituted benzanthrones: Substituent and solvent control of intersystem crossing [J].

Kapusta, P ;

Machalicky, O ;

Hrdina, R ;

Nepras, M ;

Zimmt, MB ;

Fidler, V .

JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (46) :9740-9746

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