Colorimetric probe for the detection of thiols: the dihydroazulene/vinylheptafulvene system

Martina Cacciarini; Eduardo Antonio Della Pia; Mogens Brøndsted Nielsen

doi:10.1002/ejoc.201200887

Colorimetric probe for the detection of thiols: the dihydroazulene/vinylheptafulvene system

Martina Cacciarini, Eduardo Antonio Della Pia, Mogens Brøndsted Nielsen

Kemisk Institut

9 Citationer (Scopus)

Abstract

A new application of the dihydroazulene/vinylheptafulvene (DHA/VHF) system as a chemodosimeter for thiols is reported herein. A color change visible to the naked eye can be detected in acetonitrile/water (4:1) in the presence of cysteine and alkanethiols but not with other amino acids. The higher reactivity of DHA towards cysteine compared with VHF has been demonstrated. The easy synthesis of the main core and its versatility in terms of structural and physicochemical changes are essential elements for developing a new family of thiol-specific probes with higher selectivity and sensitivity than the reported prototype. Can the dihydroazulene/vinylheptafulvene (DHA/VHF) photo/thermoswitch system be used as a chemodosimeter for thiols? A new application for this versatile system has been discovered.

Originalsprog	Engelsk
Tidsskrift	European Journal of Organic Chemistry
Vol/bind	2012
Udgave nummer	30
Sider (fra-til)	6064-6069
Antal sider	6
ISSN	1434-193X
DOI	https://doi.org/10.1002/ejoc.201200887
Status	Udgivet - okt. 2012

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10.1002/ejoc.201200887

Citationsformater

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title = "Colorimetric probe for the detection of thiols: the dihydroazulene/vinylheptafulvene system",

abstract = "A new application of the dihydroazulene/vinylheptafulvene (DHA/VHF) system as a chemodosimeter for thiols is reported herein. A color change visible to the naked eye can be detected in acetonitrile/water (4:1) in the presence of cysteine and alkanethiols but not with other amino acids. The higher reactivity of DHA towards cysteine compared with VHF has been demonstrated. The easy synthesis of the main core and its versatility in terms of structural and physicochemical changes are essential elements for developing a new family of thiol-specific probes with higher selectivity and sensitivity than the reported prototype. Can the dihydroazulene/vinylheptafulvene (DHA/VHF) photo/thermoswitch system be used as a chemodosimeter for thiols? A new application for this versatile system has been discovered.",

author = "Martina Cacciarini and {Della Pia}, {Eduardo Antonio} and Nielsen, {Mogens Br{\o}ndsted}",

year = "2012",

month = oct,

doi = "10.1002/ejoc.201200887",

language = "English",

volume = "2012",

pages = "6064--6069",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

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TY - JOUR

T1 - Colorimetric probe for the detection of thiols

T2 - the dihydroazulene/vinylheptafulvene system

AU - Cacciarini, Martina

AU - Della Pia, Eduardo Antonio

AU - Nielsen, Mogens Brøndsted

PY - 2012/10

Y1 - 2012/10

N2 - A new application of the dihydroazulene/vinylheptafulvene (DHA/VHF) system as a chemodosimeter for thiols is reported herein. A color change visible to the naked eye can be detected in acetonitrile/water (4:1) in the presence of cysteine and alkanethiols but not with other amino acids. The higher reactivity of DHA towards cysteine compared with VHF has been demonstrated. The easy synthesis of the main core and its versatility in terms of structural and physicochemical changes are essential elements for developing a new family of thiol-specific probes with higher selectivity and sensitivity than the reported prototype. Can the dihydroazulene/vinylheptafulvene (DHA/VHF) photo/thermoswitch system be used as a chemodosimeter for thiols? A new application for this versatile system has been discovered.

AB - A new application of the dihydroazulene/vinylheptafulvene (DHA/VHF) system as a chemodosimeter for thiols is reported herein. A color change visible to the naked eye can be detected in acetonitrile/water (4:1) in the presence of cysteine and alkanethiols but not with other amino acids. The higher reactivity of DHA towards cysteine compared with VHF has been demonstrated. The easy synthesis of the main core and its versatility in terms of structural and physicochemical changes are essential elements for developing a new family of thiol-specific probes with higher selectivity and sensitivity than the reported prototype. Can the dihydroazulene/vinylheptafulvene (DHA/VHF) photo/thermoswitch system be used as a chemodosimeter for thiols? A new application for this versatile system has been discovered.

U2 - 10.1002/ejoc.201200887

DO - 10.1002/ejoc.201200887

M3 - Journal article

SN - 1434-193X

VL - 2012

SP - 6064

EP - 6069

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 30

ER -

Colorimetric probe for the detection of thiols: the dihydroazulene/vinylheptafulvene system

Abstract

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