A spiropyran with enhanced fluorescence: A bright, photostable and red-emitting calcium sensor

Sylvia, Georgina M.; Heng, Sabrina; Bachhuka, Akash; Ebendorff‐Heidepriem, Heike; Abell, Andrew D.

doi:10.1016/j.tet.2017.11.020

Cited by 18 publications

(6 citation statements)

References 38 publications

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“…The most functional calcium-sensitive fluorescent sensors are ratiometric probes with dual excitation wavelengths based on fluorescein or rhodamine dye derivatives. , However, these ratiometric calcium-sensitive sensors suffer from some disadvantages such as their homogeneity and excitation in the UV region . Other calcium-sensitive fluorescent probes are reported based on homogeneous indicators such as coumarin and its derivatives, spiropyran photochromic compounds, , with the same disadvantages that were mentioned above.…”

Section: Resultsmentioning

confidence: 99%

“…7,9 However, these ratiometric calcium-sensitive sensors suffer from some disadvantages such as their homogeneity and excitation in the UV region. 3 Other calcium-sensitive fluorescent probes are reported based on homogeneous indicators such as coumarin and its derivatives, 50 spiropyran photochromic compounds, 2,51 with the same disadvantages that were mentioned above.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Sensitive Ratiometric Fluorescent Metal-Organic Framework Sensor for Calcium Signaling in Human Blood Ionic Concentration Media

Bagheri

Masoomi

2020

ACS Appl. Mater. Interfaces

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A two-dimensional fluorescent metal-organic framework (MOF) sensor, TMU-5S, was synthesized by introducing rhodamine B into the framework of TMU-5. This dye-sensitized MOF was explored as a ratiometric fluorescent sensor for Ca2+ signaling in the presence of interfering cations in ionic concentrations similar to that of blood plasma that exhibits exceptional sensitivity and selectivity to Ca2+ and faster response and recovery times than any other reported fluorescent sensor. This can be attributed to strong electrostatic interactions between basic azine groups in the narrow pore walls of TMU-5S and Ca2+ as hard–hard acid–base interactions. The results show that the two-dimensional signal transduction can reduce interfering responses from the environment and thus create exceptional sensitivity.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Sensitive Ratiometric Fluorescent Metal-Organic Framework Sensor for Calcium Signaling in Human Blood Ionic Concentration Media

Bagheri

Masoomi

2020

ACS Appl. Mater. Interfaces

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“…Fluorophore‐tagged spiropyrans have been successfully employed in important sensing and switching applications; for instance, as dyes for super resolved microscopy [52] and as ratiometric/FRET‐based fluorescence probes [8,53,54] . Furthermore, covalent attachment of fluorophores to spiropyrans has been shown to significantly enhance the fluorescence signal of the spiropyran nucleus, and this has been used to generate optically brighter sensors [55] . To highlight the power of our methodology to deliver such functional molecules rapidly, cheaply, easily and in high yield, we synthesised bis‐naphthylspiropyran 7 bp in one‐pot (72 %), directly from indole 12 (accessed by N ‐alkylation of 2‐methylindole), and commercially available naphthyl and salicylaldehyde components (Scheme 10).…”

Section: Indole C‐alkylation‐c‐alkylation‐condensationmentioning

confidence: 99%

“…[8,53,54] Furthermore, covalent attachment of fluorophores to spiropyrans has been shown to significantly enhance the fluorescence signal of the spiropyran nucleus, and this has been used to generate optically brighter sensors. [55] To highlight the power of our methodology to deliver such functional molecules rapidly, cheaply, easily and in high yield, we synthesised bis-naphthylspiropyran 7 bp in one-pot (72 %), directly from indole 12 (accessed by N-alkylation of 2-methylindole), and commercially available naphthyl and salicylaldehyde components (Scheme 10). Spiropyran 7 bp possesses a core structure known to bind selectively to M 2 + cations (through inclusion of OMe and alkylcarboxylate chelation sites) [17] whilst also incorporating fluorescent naphthyl groups for potential fluorescence enhancement and ratiometric/FRET-based visualisation and quantification.…”

Section: Indole C-alkylation-c-alkylation-condensationmentioning

confidence: 99%

Three Complementary One‐Pot Four‐Component Reaction Sequences for Rapid, General and Direct Spiropyran Synthesis

Hughes-Whiffing

Perry

2022

Eur J Org Chem

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Three one-pot three-step four-component reaction sequences for spiropyran synthesis have been developed, based around three different methods for in situ generation of 1,2,3trisubstituted indoles (indole N-alkylation, Fischer indolisation and indole C-alkylation). The reaction sequences give access to a broad swathe of spiropyran structures. Each sequence is operationally straightforward, rapid and high yielding. We have synthesized 58 structurally diverse spiropyrans bearing a wide range of useful functional groups, and their utility were demonstrated in the targeted synthesis of potential ratiometric fluorescence probes for metal ions and spiropyran-cholesterol conjugates. Finally, we showed that our one-pot N-alkylation-Calkylation-condensation sequence can underpin combinatorial spiropyran synthesis through generation of a 16-member spiropyran library.

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“…Due to their photo-switching properties, spiropyran derivatives have a wide range of applications, from design of smart nanomaterials to optical regulation of biomacromolecules [12]. Specifically, spiropyrans have been used in solution, blended in nanomaterials and polymers to develop sensors for various target molecules [13][14][15][16][17][18][19][20][21]. These sensors rely on the colorimetric and spectral variations in the spiropyrans occurring due to protonation by and complex formation with the target material.…”

Section: Introductionmentioning

confidence: 99%

Spiropyran as a potential molecular diagnostic tool for double-stranded RNA detection

et al. 2019

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Background: Long double-stranded RNAs (dsRNAs) are duplex RNAs that can induce immune response when present in mammalian cells. These RNAs are historically associated with viral replication, but recent evidence suggests that human cells naturally encode endogenous dsRNAs that can regulate antiviral machineries in cellular contexts beyond immune response.Results: In this study, we use photochromic organic compound spiropyran to profile and quantitate dsRNA expression. We show that the open form of spiropyran, merocyanine, can intercalate between RNA base pairs, which leads to protonation and alteration in the spectral property of the compound. By quantifying the spectral change, we can detect and quantify dsRNA expression level, both synthetic and cellular. We further demonstrate that spiropyrans can be used as a molecular diagnostic tool to profile endogenously expressed dsRNAs. Particularly, we show that spiropyrans can robustly detect elevated dsRNA levels when colorectal cancer cells are treated with 5-aza-2′-deoxycytidine, an FDAapproved DNA-demethylating agent used for chemotherapy, thus demonstrating the use of spiropyran for predicting responsiveness to the drug treatment. Conclusion:As dsRNAs are signature of virus and accumulation of dsRNAs is implicated in various degenerative disease, our work establishes potential application of spiropyrans as a simple spectral tool to diagnose human disease based on dsRNA expression.

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A spiropyran with enhanced fluorescence: A bright, photostable and red-emitting calcium sensor

Cited by 18 publications

References 38 publications

Sensitive Ratiometric Fluorescent Metal-Organic Framework Sensor for Calcium Signaling in Human Blood Ionic Concentration Media

Sensitive Ratiometric Fluorescent Metal-Organic Framework Sensor for Calcium Signaling in Human Blood Ionic Concentration Media

Three Complementary One‐Pot Four‐Component Reaction Sequences for Rapid, General and Direct Spiropyran Synthesis

Spiropyran as a potential molecular diagnostic tool for double-stranded RNA detection

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