ArticlePhotochemistry and photobiology
Pyrazole-substituted near-infrared cyanine dyes exhibit pH-dependent fluorescence lifetime properties.
Article in Photochemistry and photobiology. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed, 24 citations in OpenAlex.
- Synthesis and Antiproliferative Activity of 2,4,6,7-Tetrasubstituted-2Molecules (Basel, Switzerland) · 2021Article
- Copper-Catalyzed Syntheses of Pyrene-Pyrazole Pharmacophores and Structure Activity Studies for Tubulin Polymerization.ACS omega · 2018Article
- Synthesis and Optical Properties of Near-Infrared meso-Phenyl-Substituted Symmetric Heptamethine Cyanine Dyes.Molecules (Basel, Switzerland) · 2018Article
- In vivo quantitative imaging of tumor pH by nanosonophore assisted multispectral photoacoustic imaging.Nature communications · 2017Article
- Cyanine polyene reactivity: scope and biomedical applications.Organic & biomolecular chemistry · 2015Review
- Synthesis of nitric oxide probes with fluorescence lifetime sensitivity.Organic & biomolecular chemistry · 2013Article
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5 authors at 1 institution in 1 country.
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Abstract
Near-infrared heptamethine cyanine dye is functionalized with pyrazole derivatives at the meso-position to induce pH-dependent photophysical properties. The presence of pyrazole unsubstituted at (1) N-position is essential to induce pH-dependent fluorescence intensity and lifetime changes in these dyes. Replacement of meso-chloro group of cyanine dye IR820 with (1) N-unsubstituted pyrazole resulted in the pH-dependent fluorescence lifetime changes from 0.93 ns in neutral media to 1.27 ns in acidic media in DMSO. Time-resolved emission spectra (TRES) revealed that at lower pH, the pyrazole consists of fluorophores with two distinct lifetimes, which cor-responds to pH-sensitive and non-pH-sensitive species. In contrast, (1) N-substituted pyrazoles do not exhibit pH response, suggesting excited state electron transfer as the mechanism of pH-dependent fluorescence lifetime sensitivity for this class of compounds.
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