Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore

Yosuke Hisamatsu; Takehiro Fukiage; Kojiro Honma; Andrii G. Balia; Naoki Umezawa; Nobuki Kato; Tsunehiko Higuchi

doi:10.1021/acs.orglett.8b03913

Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore

Yosuke Hisamatsu, Takehiro Fukiage, Kojiro Honma, Andrii G. Balia, Naoki Umezawa, Nobuki Kato, Tsunehiko Higuchi

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

2 Citations (Scopus)

Abstract

A pioneering chemiluminescent molecule reported by Schaap and co-workers, 3-(2′-spiroadamantane)-4-methoxy-4-(3″-hydroxy)phenyl-1,2-dioxetane (AMPD), does not require enzymatic activation but is unsuitable for use under physiological conditions. To overcome this limitation, we have developed a new AMPD derivative that contains an acetamido group at the ortho position of the hydroxy group as an intramolecular hydrogen-bonding site in order to lower the pK _a value. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range.

Original language	English
Pages (from-to)	1258-1262
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.8b03913
Publication status	Published - 2019 Mar 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.8b03913

Cite this

@article{182ff860b93040798b533ea07c690362,

title = "Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore",

abstract = " A pioneering chemiluminescent molecule reported by Schaap and co-workers, 3-(2′-spiroadamantane)-4-methoxy-4-(3″-hydroxy)phenyl-1,2-dioxetane (AMPD), does not require enzymatic activation but is unsuitable for use under physiological conditions. To overcome this limitation, we have developed a new AMPD derivative that contains an acetamido group at the ortho position of the hydroxy group as an intramolecular hydrogen-bonding site in order to lower the pK a value. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range.",

author = "Yosuke Hisamatsu and Takehiro Fukiage and Kojiro Honma and Balia, {Andrii G.} and Naoki Umezawa and Nobuki Kato and Tsunehiko Higuchi",

note = "Funding Information: This work was supported by JSPS KAKENHI (No. 18K06551 for Y.H. and No. 17H04000 for T.H.) Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = mar,

day = "1",

doi = "10.1021/acs.orglett.8b03913",

language = "English",

volume = "21",

pages = "1258--1262",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore

AU - Hisamatsu, Yosuke

AU - Fukiage, Takehiro

AU - Honma, Kojiro

AU - Balia, Andrii G.

AU - Umezawa, Naoki

AU - Kato, Nobuki

AU - Higuchi, Tsunehiko

PY - 2019/3/1

Y1 - 2019/3/1

N2 - A pioneering chemiluminescent molecule reported by Schaap and co-workers, 3-(2′-spiroadamantane)-4-methoxy-4-(3″-hydroxy)phenyl-1,2-dioxetane (AMPD), does not require enzymatic activation but is unsuitable for use under physiological conditions. To overcome this limitation, we have developed a new AMPD derivative that contains an acetamido group at the ortho position of the hydroxy group as an intramolecular hydrogen-bonding site in order to lower the pK a value. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range.

AB - A pioneering chemiluminescent molecule reported by Schaap and co-workers, 3-(2′-spiroadamantane)-4-methoxy-4-(3″-hydroxy)phenyl-1,2-dioxetane (AMPD), does not require enzymatic activation but is unsuitable for use under physiological conditions. To overcome this limitation, we have developed a new AMPD derivative that contains an acetamido group at the ortho position of the hydroxy group as an intramolecular hydrogen-bonding site in order to lower the pK a value. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range.

UR - http://www.scopus.com/inward/record.url?scp=85061911684&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85061911684&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b03913

DO - 10.1021/acs.orglett.8b03913

M3 - Article

C2 - 30767544

AN - SCOPUS:85061911684

VL - 21

SP - 1258

EP - 1262

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 5

ER -

Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this