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A colorimetric and fluorescent dual probe for specific detection of cysteine based on intramolecular nucleophilic aromatic substitution.

The Analyst (2012-09-13)
Limin Ma, Junhong Qian, Haiyu Tian, Minbo Lan, Weibing Zhang
ABSTRACT

4-Nitro-1,8-naphthalic anhydride (NNA) was used to distinguish cysteine from homocysteine and other potentially interfering thiols through a novel sequential substitution mechanism. The discrimination involves a blue-fluorescent thioether formation via nucleophilic aromatic substitution of the nitro group by thiol, followed by a second intramolecular nucleophilic aromatic substitution of alkylthio with the amino group to give the green-fluorescent 4-amino derivative. NNA is highly selective towards Cys, and the detection limit of Cys by this method is 0.3 μM.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1,8-Naphthalic anhydride
Sigma-Aldrich
Atto 488 maleimide, BioReagent, suitable for fluorescence, ≥90% (coupling to thiols)
Sigma-Aldrich
Atto 565 maleimide, BioReagent, suitable for fluorescence
Sigma-Aldrich
Atto 425 maleimide, BioReagent, suitable for fluorescence, ≥70% (coupling to thiols)
Sigma-Aldrich
Atto 465 maleimide, BioReagent, suitable for fluorescence, ≥90% (coupling to thiols)
Sigma-Aldrich
Atto 495 maleimide, BioReagent, suitable for fluorescence
Sigma-Aldrich
Atto 540 Q maleimide, ≥90% (coupling to thiols)

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