4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

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4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications. / Govdi, Anastasia I.; Tokareva, Polina V.; Rumyantsev, Andrey M.; Panov, Maxim S.; Stellmacher, Johannes; Alexiev, Ulrike; Danilkina, Natalia A.; Balova, Irina A.

In: Molecules (Basel, Switzerland), Vol. 27, No. 10, 3191, 17.05.2022.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{375d2cc722b2441d90afd88340b5793d,

title = "4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications",

abstract = "Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push-pull chromophores: 4,5-bis(arylethynyl)-1 H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles' application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules. ",

keywords = "Cycloaddition Reaction, Diynes, HEK293 Cells, HeLa Cells, Humans, Triazoles/pharmacology, azide–alkyne cycloaddition, fluorescence, 1,3-diynes, bioimaging, 1,2,3-triazoles, cytotoxicity, Sonogashira cross-coupling",

author = "Govdi, {Anastasia I.} and Tokareva, {Polina V.} and Rumyantsev, {Andrey M.} and Panov, {Maxim S.} and Johannes Stellmacher and Ulrike Alexiev and Danilkina, {Natalia A.} and Balova, {Irina A.}",

note = "Publisher Copyright: {\textcopyright} 2022 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2022",

month = may,

day = "17",

doi = "10.3390/molecules27103191",

language = "English",

volume = "27",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "10",

}

RIS

TY - JOUR

T1 - 4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

AU - Govdi, Anastasia I.

AU - Tokareva, Polina V.

AU - Rumyantsev, Andrey M.

AU - Panov, Maxim S.

AU - Stellmacher, Johannes

AU - Alexiev, Ulrike

AU - Danilkina, Natalia A.

AU - Balova, Irina A.

PY - 2022/5/17

Y1 - 2022/5/17

N2 - Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push-pull chromophores: 4,5-bis(arylethynyl)-1 H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles' application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.

AB - Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push-pull chromophores: 4,5-bis(arylethynyl)-1 H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles' application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.

KW - Cycloaddition Reaction

KW - Diynes

KW - HEK293 Cells

KW - HeLa Cells

KW - Humans

KW - Triazoles/pharmacology

KW - azide–alkyne cycloaddition

KW - fluorescence

KW - 1,3-diynes

KW - bioimaging

KW - 1,2,3-triazoles

KW - cytotoxicity

KW - Sonogashira cross-coupling

UR - https://www.mendeley.com/catalogue/bf8afb29-cabc-334b-b5f5-5c819b3f93b7/

UR - http://www.scopus.com/inward/record.url?scp=85130988540&partnerID=8YFLogxK

U2 - 10.3390/molecules27103191

DO - 10.3390/molecules27103191

M3 - Article

C2 - 35630673

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 10

M1 - 3191

ER -

ID: 95374286