Synthesis and Spectral Properties of 8-Anilinonaphthalene-1-sulfonic Acid (ANS) Derivatives Prepared by Microwave-Assisted Copper(0)-Catalyzed Ullmann Reaction

Nan Wang; Erik B. Faber; Gunda I. Georg

doi:10.1021/acsomega.9b03002

Synthesis and Spectral Properties of 8-Anilinonaphthalene-1-sulfonic Acid (ANS) Derivatives Prepared by Microwave-Assisted Copper(0)-Catalyzed Ullmann Reaction

Nan Wang, Erik B. Faber, Gunda I. Georg

Medicinal Chemistry

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

11 Scopus citations

Abstract

For decades, the dye 8-anilino-1-naphthalenesulfonic acid (ANS) has been used to study biological systems due to its environmentally sensitive fluorescent nature and propensity to bind to hydrophobic pockets of proteins. However, the syntheses of ANS and its derivatives have been low yielding, requiring harsh reaction conditions and long reaction times. We have developed efficient, mild microwave-assisted copper(0)-catalyzed Ullmann coupling conditions to synthesize ANS derivatives with yields of up to 74%. Many of these derivatives have spectral properties distinct from ANS, including improved and diminished quantum yields, different absorption and emission maxima, and complete loss of fluorescence. ANS derivatives with these unique fluorescence properties are useful tools to study biological systems.

Original language	English (US)
Pages (from-to)	18472-18477
Number of pages	6
Journal	ACS Omega
Volume	4
Issue number	19
DOIs	https://doi.org/10.1021/acsomega.9b03002
State	Published - Nov 5 2019

Bibliographical note

Funding Information:
This research was supported by a grant from the Eunice Kennedy Shriver National Institute of Child Health and Human Development (R01 HD094373). E.B.F. was supported by NIH training grants from the National Institute of General Medical Sciences (T32 GM008244 and T32 GM00870020) and by a Ruth L. Kirschstein National Research Service Award from the National Cancer Institute (F30 CA232303). We would like to acknowledge Dr. Ernst Schönbrunn for his preliminary work exploring the fluorescence properties of ANS derivatives.

Funding Information:
This research was supported by a grant from the Eunice Kennedy Shriver National Institute of Child Health and Human Development (R01 HD094373). E.B.F. was supported by NIH training grants from the National Institute of General Medical Sciences (T32 GM008244 and T32 GM00870020) and by a Ruth L. Kirschstein National Research Service Award from the National Cancer Institute (F30 CA232303). We would like to acknowledge Dr. Ernst Schonbrunn for his preliminary work exploring the fluorescence properties of ANS derivatives.

Publisher Copyright:
© 2019 American Chemical Society.

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10.1021/acsomega.9b03002

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abstract = "For decades, the dye 8-anilino-1-naphthalenesulfonic acid (ANS) has been used to study biological systems due to its environmentally sensitive fluorescent nature and propensity to bind to hydrophobic pockets of proteins. However, the syntheses of ANS and its derivatives have been low yielding, requiring harsh reaction conditions and long reaction times. We have developed efficient, mild microwave-assisted copper(0)-catalyzed Ullmann coupling conditions to synthesize ANS derivatives with yields of up to 74%. Many of these derivatives have spectral properties distinct from ANS, including improved and diminished quantum yields, different absorption and emission maxima, and complete loss of fluorescence. ANS derivatives with these unique fluorescence properties are useful tools to study biological systems.",

author = "Nan Wang and Faber, {Erik B.} and Georg, {Gunda I.}",

note = "Funding Information: This research was supported by a grant from the Eunice Kennedy Shriver National Institute of Child Health and Human Development (R01 HD094373). E.B.F. was supported by NIH training grants from the National Institute of General Medical Sciences (T32 GM008244 and T32 GM00870020) and by a Ruth L. Kirschstein National Research Service Award from the National Cancer Institute (F30 CA232303). We would like to acknowledge Dr. Ernst Sch{\"o}nbrunn for his preliminary work exploring the fluorescence properties of ANS derivatives. Funding Information: This research was supported by a grant from the Eunice Kennedy Shriver National Institute of Child Health and Human Development (R01 HD094373). E.B.F. was supported by NIH training grants from the National Institute of General Medical Sciences (T32 GM008244 and T32 GM00870020) and by a Ruth L. Kirschstein National Research Service Award from the National Cancer Institute (F30 CA232303). We would like to acknowledge Dr. Ernst Schonbrunn for his preliminary work exploring the fluorescence properties of ANS derivatives. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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Synthesis and Spectral Properties of 8-Anilinonaphthalene-1-sulfonic Acid (ANS) Derivatives Prepared by Microwave-Assisted Copper(0)-Catalyzed Ullmann Reaction

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