Azadioxatriangulenium: synthesis and photophysical properties of reactive dyes for bioconjugation

TY - JOUR

T1 - Azadioxatriangulenium

T2 - synthesis and photophysical properties of reactive dyes for bioconjugation

AU - Bora, Ilkay

AU - Bogh, Sidsel Ammitzbøll

AU - Santella, Marco

AU - Rosenberg, Martin

AU - Sørensen, Thomas Just

AU - Laursen, Bo Wegge

PY - 2015/10/1

Y1 - 2015/10/1

N2 - Azadioxatriangulenium (ADOTA) is a fluorescent triangulenium dye with a long fluorescence lifetime, highly polarized transitions and emission in the red part of the visible spectrum. These properties make the chromophore suited for application in fluorescence polarization/anisotropy assays. To be useful for these applications, reactive forms of the dyes must be available in significant quantities. Here, the synthesis and photophysical properties of amine-reactive N-hydroxysuccinimide (NHS) esters and a thiol-reactive maleimide derivative of ADOTA are reported. The synthesis involves two steps of nucleophilic bridge-forming reactions starting from tris(2,6-dimethoxyphenyl)methylium tetrafluoroborate, which can readily be prepared on a 100 g scale. In the third and final step the reactive NHS or maleimide groups are formed. The beneficial photophysical properties of the ADOTA chromophore are maintained in these derivatives, and we conclude that these systems are ideal to study protein motion and protein-protein interactions for systems of up to 1000 kDa. Azadioxatriangulenium or ADOTA has been synthesized with reactive groups for conjugation to amino and thiol groups of biomolecules. The long fluorescence lifetime of the red ADOTA dye allows for new developments in florescence polarization assays, enabled by the detailed account of the synthesis of four ADOTA derivatives presented here.

AB - Azadioxatriangulenium (ADOTA) is a fluorescent triangulenium dye with a long fluorescence lifetime, highly polarized transitions and emission in the red part of the visible spectrum. These properties make the chromophore suited for application in fluorescence polarization/anisotropy assays. To be useful for these applications, reactive forms of the dyes must be available in significant quantities. Here, the synthesis and photophysical properties of amine-reactive N-hydroxysuccinimide (NHS) esters and a thiol-reactive maleimide derivative of ADOTA are reported. The synthesis involves two steps of nucleophilic bridge-forming reactions starting from tris(2,6-dimethoxyphenyl)methylium tetrafluoroborate, which can readily be prepared on a 100 g scale. In the third and final step the reactive NHS or maleimide groups are formed. The beneficial photophysical properties of the ADOTA chromophore are maintained in these derivatives, and we conclude that these systems are ideal to study protein motion and protein-protein interactions for systems of up to 1000 kDa. Azadioxatriangulenium or ADOTA has been synthesized with reactive groups for conjugation to amino and thiol groups of biomolecules. The long fluorescence lifetime of the red ADOTA dye allows for new developments in florescence polarization assays, enabled by the detailed account of the synthesis of four ADOTA derivatives presented here.

KW - Fluorescence spectroscopy, Dyes/pigments, Aromatic substitution, Triangulenium, Bioconjugate chemistry

U2 - 10.1002/ejoc.201500888

DO - 10.1002/ejoc.201500888

M3 - Journal article

C2 - 27047257

SN - 1434-193X

VL - 2015

SP - 6351

EP - 6358

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 28

ER -