2021
DOI: 10.1002/chem.202101990
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Native Chemical Ligation‐Based Fluorescent Probes for Cysteine and Aminopeptidase N Using meso‐thioester‐BODIPY

Abstract: meso-Carboxyl-BODIPY responds to small electronic changes resulting from acyl substitution reactions with a marked change in fluorescence. Herein, the minute changes that accompany the thioester to amide conversion encountered in native chemical ligation (NCL) are exploited in the construction of fluorescent "turn-on" probes. Two fluorogenic probes, 1 a and 4, derived from a mesothioester-BODIPY scaffold, were designed for the selective detection of cysteine (1 a) and aminopeptidase N (4), respectively. The ar… Show more

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Cited by 12 publications
(5 citation statements)
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“…Summarizing, the reactivity of thiocyanuric acid alkyl esters toward unprotected 2-mercaptoalkylamines under mild basic conditions is practically limited to mono- or occasionally disubstitution throughout an irreversible ligation reaction (Scheme ), which is of little importance from the point of view of dynamic covalent chemistry. However, we believe that the described reactivity may be useful for the design of new selective reagents for the derivatization of cysteamines, similar to the recently published fluorescence probes based on ligation of cysteinyl-peptides to a meso -thioester-BODIPY …”
Section: Resultsmentioning
confidence: 52%
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“…Summarizing, the reactivity of thiocyanuric acid alkyl esters toward unprotected 2-mercaptoalkylamines under mild basic conditions is practically limited to mono- or occasionally disubstitution throughout an irreversible ligation reaction (Scheme ), which is of little importance from the point of view of dynamic covalent chemistry. However, we believe that the described reactivity may be useful for the design of new selective reagents for the derivatization of cysteamines, similar to the recently published fluorescence probes based on ligation of cysteinyl-peptides to a meso -thioester-BODIPY …”
Section: Resultsmentioning
confidence: 52%
“…However, we believe that the described reactivity may be useful for the design of new selective reagents for the derivatization of cysteamines, similar to the recently published fluorescence probes based on ligation of cysteinyl-peptides to a meso-thioester-BODIPY. 5 Thiols Exchange. Due to the limitations of the abovediscussed ligation reactions, we focused on the transthioesterification of thiocyanurates with compounds containing a free sulfhydryl group.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…The proposed detection mechanisms of CySI to distinguish Cys and Hcy are illustrated in Scheme . Several researches have shown that thioester and thioether-cyanine derivatives are highly susceptive to thiols. Considering that the p K a of Cys (8.30) is lower than those of Hcy (10.00) and GSH (9.20), the nucleophilic ability of sulfhydryl on Cys toward the thioester bond is much stronger than those of Hcy and GSH.…”
Section: Resultsmentioning
confidence: 99%
“…Similar to the well-established methods for amine conjugation using cleavable moieties, the group of Kim adapted their meso-carboxyBODIPY 30 probe and achieved a remarkable turn-on effect upon reaction of its activated acid, 131 initially with the NHS-30a and PFP 30b esters (Figure 12) and later also with thioester 30c. 132 Using their PFP derivative 30b, they showed a 3000-fold increase in fluorescence upon reaction with MeNH 2 under physiological conditions in less than 5 min. A similar rate was observed for simple primary aliphatic mono-and diamines.…”
Section: Amide Formation Via Activated Ester Cleavagementioning
confidence: 99%