Fluorescence detection of serum albumin with a turnover-based sensor utilizing Kemp elimination reaction

Shingo Sakamoto; Toru Komatsu; Tasuku Ueno; Kenjiro Hanaoka; Yasuteru Urano

doi:10.1016/j.bmcl.2017.05.076

Fluorescence detection of serum albumin with a turnover-based sensor utilizing Kemp elimination reaction

Shingo Sakamoto, Toru Komatsu, Tasuku Ueno, Kenjiro Hanaoka, Yasuteru Urano

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

9 Citations (Scopus)

Abstract

The Kemp elimination reaction is a well-known chemical reaction that is facilitated on a protein surface microenvironment, and in particular is highly accelerated in a unique binding pocket of serum albumin. We have designed and synthesized a fluorescently activatable coumarin derivative with a benzisoxazole scaffold to enable monitoring of the Kemp elimination reaction in terms of fluorescence change for the first time. We show that this fluorescent sensor can sensitively and selectively quantitate serum albumin in blood samples. It also works in a dry-chemistry format.

Original language	English
Pages (from-to)	3464-3467
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	27
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2017.05.076
Publication status	Published - 2017
Externally published	Yes

Keywords

Chemical biology
Enzymes
Fluorescent probes
Kemp elimination
Proteins

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2017.05.076

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title = "Fluorescence detection of serum albumin with a turnover-based sensor utilizing Kemp elimination reaction",

abstract = "The Kemp elimination reaction is a well-known chemical reaction that is facilitated on a protein surface microenvironment, and in particular is highly accelerated in a unique binding pocket of serum albumin. We have designed and synthesized a fluorescently activatable coumarin derivative with a benzisoxazole scaffold to enable monitoring of the Kemp elimination reaction in terms of fluorescence change for the first time. We show that this fluorescent sensor can sensitively and selectively quantitate serum albumin in blood samples. It also works in a dry-chemistry format.",

keywords = "Chemical biology, Enzymes, Fluorescent probes, Kemp elimination, Proteins",

author = "Shingo Sakamoto and Toru Komatsu and Tasuku Ueno and Kenjiro Hanaoka and Yasuteru Urano",

note = "Funding Information: This work was financially supported by MEXT (24655147, 15H05371, and 15K14937 to T.K., and 16H05099, 16H00823 to K.H.), JST (T.K. and K.H.), AMED (Y.U.), and JSPS (Core-to-Core Program, A. Advanced Research Networks). T.K. was supported by Naito Foundation and Mochida Memorial Foundation for Medical and Pharmaceutical Research. Authors would like to thank Yugo Kuriki for assistance with the dry-chemistry experiments. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.bmcl.2017.05.076",

language = "English",

volume = "27",

pages = "3464--3467",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Fluorescence detection of serum albumin with a turnover-based sensor utilizing Kemp elimination reaction

AU - Sakamoto, Shingo

AU - Komatsu, Toru

AU - Ueno, Tasuku

AU - Hanaoka, Kenjiro

AU - Urano, Yasuteru

N1 - Funding Information: This work was financially supported by MEXT (24655147, 15H05371, and 15K14937 to T.K., and 16H05099, 16H00823 to K.H.), JST (T.K. and K.H.), AMED (Y.U.), and JSPS (Core-to-Core Program, A. Advanced Research Networks). T.K. was supported by Naito Foundation and Mochida Memorial Foundation for Medical and Pharmaceutical Research. Authors would like to thank Yugo Kuriki for assistance with the dry-chemistry experiments. Publisher Copyright: © 2017 Elsevier Ltd

PY - 2017

Y1 - 2017

N2 - The Kemp elimination reaction is a well-known chemical reaction that is facilitated on a protein surface microenvironment, and in particular is highly accelerated in a unique binding pocket of serum albumin. We have designed and synthesized a fluorescently activatable coumarin derivative with a benzisoxazole scaffold to enable monitoring of the Kemp elimination reaction in terms of fluorescence change for the first time. We show that this fluorescent sensor can sensitively and selectively quantitate serum albumin in blood samples. It also works in a dry-chemistry format.

AB - The Kemp elimination reaction is a well-known chemical reaction that is facilitated on a protein surface microenvironment, and in particular is highly accelerated in a unique binding pocket of serum albumin. We have designed and synthesized a fluorescently activatable coumarin derivative with a benzisoxazole scaffold to enable monitoring of the Kemp elimination reaction in terms of fluorescence change for the first time. We show that this fluorescent sensor can sensitively and selectively quantitate serum albumin in blood samples. It also works in a dry-chemistry format.

KW - Chemical biology

KW - Enzymes

KW - Fluorescent probes

KW - Kemp elimination

KW - Proteins

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SN - 0960-894X

VL - 27

SP - 3464

EP - 3467

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 15

ER -

Fluorescence detection of serum albumin with a turnover-based sensor utilizing Kemp elimination reaction

Abstract

Keywords

ASJC Scopus subject areas

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