Efficient fluorescent recognition of ATP/GTP by a water-soluble bisquinolinium pyridine-2,6-dicarboxamide compound. Crystal structures, spectroscopic studies and interaction mode with DNA

Viviano-Posadas, Alejandro O; Romero-Mendoza, Ulises; Bazany‐Rodríguez, Iván J.; Velázquez-Castillo, Rocio V.; Martı́nez-Otero, Diego; Bautista-Renedo, Joanatan M.; González‐Rivas, Nelly; Galindo‐Murillo, Rodrigo; Salomón-Flores, María K.; Dorazco‐González, Alejandro

doi:10.1039/d2ra05040d

Cited by 3 publications

(4 citation statements)

References 89 publications

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“…In our experience, completely deprotonated (pH > 10) quinolinium pyridine-2,6-dicarboxamide derivatives are practically not uorescent. 47,49,56 The rst pK a1 = 6.61 of 11 is comparable to those reported values for structurally related monoboronic acids appended quinolinium rings studied by Geddes which have pK a less than 7.0 assigned to the boronic groups from uorescence data. [44][45][46] To unambiguously assign the pK a value of boronic acid in 11, we reproduced the UV-vis pH titration in the presence of fructose (10 mM), see Fig.…”

Section: Optical and Acid-base Propertiessupporting

confidence: 82%

“…This syn – syn conformation of amide groups has been usually described for crystals of pyridine-2,6-dicarboxamide pincer-like derivatives as a consequence of intramolecular H bonds of type N–H⋯N pyridine . 49–53…”

Section: Resultsmentioning

confidence: 99%

“…This syn-syn conformation of amide groups has been usually described for crystals of pyridine-2,6-dicarboxamide pincer-like derivatives as a consequence of intramolecular H bonds of type N-H/N pyridine . [49][50][51][52][53] An inspection of the crystal of 11-SO 4 displays multiple p-p interactions mainly centered on the quinolinium rings and the central pyridine involving cofacial parallel stacked geometries with centroid-centroid distances ranging from 3.49 Å and 3.80 Å (Fig. S19 and Table S5 †).…”

Section: Synthesis and Structural Analysismentioning

confidence: 99%

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Water-soluble fluorescent chemosensor for sorbitol based on a dicationic diboronic receptor. Crystal structure and spectroscopic studies

Zamora-Moreno,

Salomón-Flores,

Valdes-García

et al. 2023

RSC Adv.

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Section: Optical and Acid-base Propertiessupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis and Structural Analysismentioning

confidence: 99%

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Water-soluble fluorescent chemosensor for sorbitol based on a dicationic diboronic receptor. Crystal structure and spectroscopic studies

Zamora-Moreno,

Salomón-Flores,

Valdes-García

et al. 2023

RSC Adv.

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“…In contrast, the binding of purine nucleobases leads to emission quenching of cyclophane 4. This fluorescence quenching of cyclophane 4 by purine nucleotides may be explained by a different binding mode of the purine nucleotides ATP, AMP, and dGMP, as compared with one of pyrimidine nucleotides, which leads to a fluorescence enhancement upon formation of the cyclophane-nucleotide complex [83][84][85]. At the same time, it cannot be excluded that the purine nucleotides bind in a similar mode as the pyrimidine nucleotides and that the fluorescence quenching by ATP, AMP, and dGMP is just the result of a stronger quenching efficiency of the purine bases.…”

Section: Discussionmentioning

confidence: 99%

Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane

Schlosser,

Hebborn,

Berdnikova

et al. 2023

Chemistry

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A styrylpyridine-containing cyclophane with diethylenetriamine linkers is presented as a host system whose association with representative nucleotides was examined with photometric and fluorimetric titrations. The spectrometric titrations revealed the formation of 1:1 complexes with log Kb values in the range of 2.3–3.2 for pyrimidine nucleotides TMP (thymidine monophosphate), TTP (thymidine triphosphate) and CMP (cytidine monophosphate) and 3.8–5.0 for purine nucleotides AMP (adenosine monophosphate), ATP (adenosine triphosphate), and dGMP (deoxyguanosine monophosphate). Notably, in a neutral buffer solution, the fluorimetric response to the complex formation depends on the type of nucleotide. Hence, quenching of the already weak fluorescence was observed with the purine bases, whereas the association of the cyclophane with pyrimidine bases TMP, TTP, and CMP resulted in a significant fluorescence light-up effect. Thus, it was demonstrated that the styrylpyridine unit is a useful and complementary fluorophore for the development of selective nucleotide-targeting fluorescent probes based on alkylamine-linked cyclophanes.

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Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position

Cesaretti

Calzoni

Montegiove

et al. 2023

IJMS

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Fluorescence imaging is constantly searching for new far-red emitting probes whose turn-on response is selective upon the interaction with specific biological targets. Cationic push-pull dyes could indeed respond to these requirements due to their intramolecular charge transfer (ICT) character, by which their optical properties can be tuned, and their ability to interact strongly with nucleic acids. Starting from the intriguing results recently achieved with some push-pull dimethylamino-phenyl dyes, two isomers obtained by switching the cationic electron acceptor head (either a methylpyridinium or a methylquinolinium) from the ortho to the para position have been scrutinized for their ICT dynamics, their affinity towards DNA and RNA, and in vitro behavior. By exploiting the marked fluorescence enhancement observed upon complexation with polynucleotides, fluorimetric titrations were employed to evaluate the dyes’ ability as efficient DNA/RNA binders. The studied compounds exhibited in vitro RNA-selectivity by localizing in the RNA-rich nucleoli and within the mitochondria, as demonstrated by fluorescence microscopy. The para-quinolinium derivative showed some modest antiproliferative effect on two tumor cell lines as well as improved properties as an RNA-selective far-red probe in terms of both turn-on response (100-fold fluorescence enhancement) and localized staining ability, attracting interest as a potential theranostic agent.

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Efficient fluorescent recognition of ATP/GTP by a water-soluble bisquinolinium pyridine-2,6-dicarboxamide compound. Crystal structures, spectroscopic studies and interaction mode with DNA

Abstract: A dicationic pyridine-2,6-dicarboxamide-based compound 1 bearing two N-alkylquinolinium units was synthesized, determined by single-crystal X-ray diffraction, and studied as a fluorescent receptor for nucleotides and inorganic phosphorylated anions in pure water.

Cited by 3 publications

References 89 publications

Water-soluble fluorescent chemosensor for sorbitol based on a dicationic diboronic receptor. Crystal structure and spectroscopic studies

Water-soluble fluorescent chemosensor for sorbitol based on a dicationic diboronic receptor. Crystal structure and spectroscopic studies

Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane

Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position

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