The synthesis and photostability of novel squarylium indocyanine dyes

Song, Bo; Zhang, Qian; Ma, Wenhui; Peng, Xiaojun; Fu, Xing; Wang, Bing-Shuai

doi:10.1016/j.dyepig.2009.03.002

Cited by 44 publications

(25 citation statements)

References 19 publications

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“…On the other hand, the solution could also filtrate most of the UV-lights, whose wavelength is shorter than 400 nm. The photostability experiment was performed in DMSO at room temperature without natural light [25]. The absorption intensity of the compound was measured after exposing to light with different time.…”

Section: Photostability Of Compoundmentioning

confidence: 99%

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Fei

Lin

et al. 2015

J Fluoresc

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A novel fluorescent dye, 1-(6-carboxyhexyl)-4-(2-(9-ethyl-carbazole-3-yl) vinyl) quinolizinium bromide, was synthesized, and its structure was characterized by (1)H NMR, (13)C-NMR, IR and HRMS. The spectra properties of this dye in different solvents and under different pH value were invest'igated preliminarily, and the results showed that its fluorescent properties was affected by the polarity and the dipole moment of the solvent. The photostability and thermostability test results showed that its photoreduction rate constant was 1.64 × 10(-5) mol/Min and its fluorescent intensity decreased little after heating at 80 °C for 6 h, suggesting the dye was quite stable. In the labeling experiment of BSA and DNA with the dye, the fluorescent all intensity increased with the addition of BSA and DNA. Specially, the dye showed an excellent turn-on effect upon binding with ctDNA.

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Section: Photostability Of Compoundmentioning

confidence: 99%

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Fei

Lin

et al. 2015

J Fluoresc

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“…9E PBIC shows an absorption maximum wavelength around 520 nm. [66][67][68] In aprotic solvents, the dipole-dipole interaction between the dye and solvents was dominant. 64 It is said that the absorption band was at about 520 nm and the fluorescent band at 600 nm, which is longer than that of BMVC.…”

Section: Absorption and Fluorescence Spectra Of 9e Pbicmentioning

confidence: 99%

A benzindole substituted carbazole cyanine dye: a novel targeting fluorescent probe for parallel c-myc G-quadruplexes

Lin

Fei

et al. 2015

Analyst

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Many organic ligands were synthesized to recognize G-quadruplexes. However, different kinds of G-quadruplexes (G4s) possess different structures and functions. Therefore, selective recognition of certain types of G4s is important for the study of G4s. In this paper, a novel cyanine dye, 3-(2-(4-vinylpyridine))-6-(2-((1-(4-sulfobutyl))-3,3-dimethyl-2-vinylbenz[e]indole)-9-ethyl-carbazole (9E PBIC), composed of benzindole and carbazole was designed and synthesised. The studies on UV-vis and fluorescence properties of the dye with different DNA forms showed that the dye exhibits almost no fluorescence under aqueous buffer conditions, but it increased over 100 fold in the presence of c-myc G4 and 10-30 fold in the presence of other G4s, while little in the presence of single/double-stranded DNA, indicating that it has excellent selectivity to c-myc 2345 G4. For the binding studies the dye is interacted with the c-myc 2345 G-quadruplex by using the end-stack binding model. It can be said that the dye is an excellent targeting fluorescent probe for c-myc G-quadruplexes.

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“…In contrast, one linear indocyanine ICy5 dye showed a fast decrease (25%) in fluorescence under the same experimental conditions (Figure S1). After exposure to air for 7 days, the emission intensity of D1 solution decreased 33%, which was explained by slow photooxidation of squarylium dye . Even in this case, its Ø f was still 0.201, which was high enough for biological experiments.…”

Section: Resultsmentioning

confidence: 88%

A Difunctional Squarylium Indocyanine Dye Distinguishes Dead Cells through Diverse Staining of the Cell Nuclei/Membranes

Guo

Shen

et al. 2013

Small

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Functionalized fluorescent dyes have attracted great interest for the specific staining of subcellular organelles in multicellular organisms. A novel nanometer-sized water-soluble multi-functional squarylium indocyanine dye (D1) that contains four primary amines is synthesized. The dye exhibits good photostability, non-toxicity and biocompatibility. Isothermal titration calorimetry demonstrates that an affinity between D1 and DNA is higher than that between D1 and analogue of phospholipids. Analysis of circular dichroism spectra indicates that D1 targets to the DNA minor groove and aggregates to a helix. Because of the distinct affinity between the dye and subcellular organelles, the dye exhibits difunctional abilities to label the cell nuclei in fixed cells/tissue and the cell membranes in live cells/tissue. By combination of the two staining capabilities, the dye is further explored as a specific marker to distinguish apoptotic cells in live cells/tissue. The research opens a new way to design novel multifunctional dyes for life science applications.

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The synthesis and photostability of novel squarylium indocyanine dyes

Cited by 44 publications

References 19 publications

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

A benzindole substituted carbazole cyanine dye: a novel targeting fluorescent probe for parallel c-myc G-quadruplexes

A Difunctional Squarylium Indocyanine Dye Distinguishes Dead Cells through Diverse Staining of the Cell Nuclei/Membranes

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