Synthesis and the Stimuli‐Responsive Characteristics of Cyclic Cholamide Nicotinamide Adenine Dinucleotide (NAD<sup>+</sup>) Derivative with Aggregation in Basic Aqueous Solution

Li, Dazhi; Yang, Yunxu; Hu, Biwei; Yang, Chao; Huo, Baolong; Wang, Aizhi; Yu, Fabiao; Li, Xue; Dong, Yajun; Fan, Weiping

doi:10.1002/ajoc.201500168

Cited by 2 publications

(1 citation statement)

References 49 publications

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“…The synthesis of receptors 3a – c was accomplished by alkylation of macrocycle 6 in acetonitrile and 5 via chloride-promoted template synthesis …”

Section: Discussionmentioning

confidence: 99%

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Morozov,

Gargiulo,

Ghule

et al. 2024

J. Am. Chem. Soc.

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The binding of nucleotides is crucial for signal transduction as it induces conformational protein changes, leading to downstream cellular responses. Synthetic receptors that bind nucleotides and transduce the binding event into global conformational rearrangements are highly challenging to design, especially those that operate in an aqueous solution. Much work is focused on evaluating functionalized dyes to detect nucleotides, whereas coupling of a nucleotide-induced conformational switching to a sensing event has not been reported to date. We disclose synthetic receptors that undergo a global conformational rearrangement upon nucleotide binding. Integrating naphthalimide and the pyridinium ion into the structure enables stabilization of the folded conformation and efficient fluorescence quenching. The binding of a nucleotide rearranges the receptor conformation and alters the strong fluorescence enhancement. The methylpyridinium-containing receptor demonstrated high sensing selectivity for adenosine 5′-triphosphate (ATP) and a record 160-fold fluorescence enhancement. It can detect fluctuations of ATP in HeLa cells and possesses low cytotoxicity. The developed systems present an attractive approach for designing ATP-responsive artificial molecular switches that operate in water and integrate a strong fluorescence response.

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“…The synthesis of receptors 3a – c was accomplished by alkylation of macrocycle 6 in acetonitrile and 5 via chloride-promoted template synthesis …”

Section: Discussionmentioning

confidence: 99%

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Morozov,

Gargiulo,

Ghule

et al. 2024

J. Am. Chem. Soc.

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Novel Rearrangement Followed by Ring Contraction of Highly Selective and Sensitive Turn‐On Chromogenic and Fluorescent Chemodosimeters for Cu²⁺ Ions

Das

Chaudhuri²,

Karmakar³

et al. 2016

Asian J Org Chem

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The dual chromogenic and fluorogenic chemodosimetric behaviour of substituted 5-amino-1,2-dihydro-2methyl-1,6-naphthyridine-8-carbonitriles was investigated. The reaction-based indicators operate by an unusualr earrangementf ollowed by ring contraction to generate ap yrro-lopyridine, with a" naked-eye"r esponse and chromofluorogenic selectives ensing for Cu 2 + ions. The structure of the pyrrolopyridine was confirmed by single-crystal X-ray analysis. Results and DiscussionThis report describes the design and synthesis of afluorometric assay towards the effective detection of Cu 2 + ions. We present, for the first time, [1,6]-naphthyridine derivatives as dosimeters with high sensitivity and selectivity,o wing to the surprising rearrangement andr ing contraction mediated by Cu 2 + ions. The dosimeters (1 and 2,S cheme 1) were synthesizedi no ne step according to our recently published work. [12] [a] P.

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Synthesis and the Stimuli‐Responsive Characteristics of Cyclic Cholamide Nicotinamide Adenine Dinucleotide (NAD⁺) Derivative with Aggregation in Basic Aqueous Solution

Cited by 2 publications

References 49 publications

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Novel Rearrangement Followed by Ring Contraction of Highly Selective and Sensitive Turn‐On Chromogenic and Fluorescent Chemodosimeters for Cu²⁺ Ions

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Synthesis and the Stimuli‐Responsive Characteristics of Cyclic Cholamide Nicotinamide Adenine Dinucleotide (NAD+) Derivative with Aggregation in Basic Aqueous Solution

Cited by 2 publications

References 49 publications

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

Novel Rearrangement Followed by Ring Contraction of Highly Selective and Sensitive Turn‐On Chromogenic and Fluorescent Chemodosimeters for Cu2+ Ions

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Synthesis and the Stimuli‐Responsive Characteristics of Cyclic Cholamide Nicotinamide Adenine Dinucleotide (NAD⁺) Derivative with Aggregation in Basic Aqueous Solution

Novel Rearrangement Followed by Ring Contraction of Highly Selective and Sensitive Turn‐On Chromogenic and Fluorescent Chemodosimeters for Cu²⁺ Ions