Synthesis and Evaluation of Polyhydroxylated Near-Infrared Carbocyanine Molecular Probes

Zhang, Zongren; Achilefu, Samuel

doi:10.1021/ol049258a

Cited by 125 publications

(79 citation statements)

References 16 publications

(17 reference statements)

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“…The weak signal may account for the omission of the blue-shifted peaks in previous reports of the fluorescence properties of these compounds. [7][8][9][10] Upon conjugation of the symmetrical dye cypate with a peptide, the resulting nonsymmetrical cypate-peptide conjugate 5 exhibited a 45 % increase in the level of the 700-nm emission band (relative to cypate), albeit still lower than the 82 % obtained with 3 and 4. Although the 100-nm blue-shifted emission peak could indicate the elimination of a methine bond from the heptamethine structure, [11] it is unlikely that the emission band at 700 nm resulted from the formation of lower homologues (such as tri-or pentamethines) of cypate or ICG, which typically have similar fluorescence lifetimes of cypate at 800 nm (namely, 0.86 ns in dimethyl sulfoxide, DMSO).…”

mentioning

confidence: 95%

Near‐Infrared Dichromic Fluorescent Carbocyanine Molecules

Zhang¹,

Berezin²,

Kao³

et al. 2008

Angew Chem Int Ed

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confidence: 95%

Near‐Infrared Dichromic Fluorescent Carbocyanine Molecules

Zhang¹,

Berezin²,

Kao³

et al. 2008

Angew Chem Int Ed

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“…Large stokes shift could help to reduce self-quenching and measurement error by excitation light and scattered light. 20 The fluorescence quantum yield of six dyes was in the region 0.0001-0.0781 in different solvents. From Table 1 it could be found that the order of fluorescence quantum yield was 3a, 3b > 3c, 3d.…”

Section: Synthesismentioning

confidence: 98%

Synthesis, absorption and fluorescence spectral characteristics of trinucleus dimethine cyanine dyes as fluorescent probes for DNA detection

Su¹,

Wang²,

Zhang³

et al. 2011

J. Braz. Chem. Soc.

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Neste trabalho descreve-se a preparação de seis corantes cianina dimetina trinucleares com núcleos de piridina, obtidos a partir da condensação de iodeto de trimetilpiridínio com aldeídos aromáticos heterocíclicos. As propriedades de absorção e fluorescência dos corantes foram estudadas em solventes com polaridades diferentes. O deslocamento hipsocrômico dos máximos de absorção dos corantes foi observado com o aumento da polaridade do solvente. Foram estudadas as propriedades fluorescentes dos corantes em solução e na presença de DNA. Foi observado um aumento significativo do rendimento quântico de fluorescência na presença de DNA para quatro corantes.. Em particular, um dos corantes emite fluorescência fraca no tampão Tris-HCl, apresentando contudo fluorescência intensa na presença de DNA.The preparation of six trinucleus dimethine cyanine dyes with pyridine nucleus obtained by the condensation of trimethylpyridinium iodides with heterocyclic aromatic aldehyde was described. The absorption and fluorescence properties of the dyes were studied in different polarity solvents. Blue shift of the maxima absorption of the dyes was observed with the increase of solvents polarity. The fluorescence properties of the dyes in solution and in presence of DNA were studied. Significant enhancement of the fluorescent quantum yield was observed in four dyes in the presence of DNA. Specially, one of six dyes emitted weak fluorescence in Tris-HCl buffer, but displayed bright fluorescence in the presence of DNA.

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“…The Stokes' shift was larger than common fluorophores such as fluorescein, rhodamine, and BODIPY, as well as cyanine dyes, which is desirable for suppressing self-quenching, minimizing measurement errors, and increasing detection sensitivity to a great extent. 35,36 The benzimidazole−Cu complex was synthesized from the reaction of compound BB with CuCl 2 in a 2:1 ratio in the presence of NaH in THF as shown in Scheme 1. The desired product was obtained with high yield and characterized with FT-IR, HR-MS, and UV−vis spectroscopies, as well as elemental analyses.…”

Section: ■ Introductionmentioning

confidence: 99%

Fluorescence Signaling of Hydrogen Sulfide in Broad pH Range Using a Copper Complex Based on BINOL–Benzimidazole Ligands

Sun

et al. 2015

Inorg. Chem.

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A weakly fluorescent complex derived from a binaphthol-benzimidazole ligand was designed and synthesized for hydrogen sulfide at different pH conditions. It was demonstrated that the probe showed the same reactivity to various hydrogen sulfide species in a broad range of pH values to generate highly fluorescent product through a displacement reaction mechanism, whereas the product's fluorescence spectrum exhibited a hypsochromic shift of ∼73 nm (2393 cm(-1)) as pH increased from neutral to basic, which can be used for distinguishing the various species of hydrogen sulfide. This turn-on fluorescence probe was highly selective and sensitive to hydrogen sulfide with a detection limit of 0.11 μM. It was then applied for evaluating the total content of sulfide (including hydrogen sulfide, hydrosulfide, and sulfide) as well as for the visual detection of gaseous H2S in air using a simple test paper strip.

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Synthesis and Evaluation of Polyhydroxylated Near-Infrared Carbocyanine Molecular Probes

Cited by 125 publications

References 16 publications

Near‐Infrared Dichromic Fluorescent Carbocyanine Molecules

Near‐Infrared Dichromic Fluorescent Carbocyanine Molecules

Synthesis, absorption and fluorescence spectral characteristics of trinucleus dimethine cyanine dyes as fluorescent probes for DNA detection

Fluorescence Signaling of Hydrogen Sulfide in Broad pH Range Using a Copper Complex Based on BINOL–Benzimidazole Ligands

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