Syntheses and DNA-binding studies of a series of unsymmetrical cyanine dyes: structural influence on the degree of minor groove binding to natural DNA

Karlsson, Håkan; Bergqvist, Mattias H.; Lincoln, Per; Westman, Gunnar

doi:10.1016/j.bmc.2004.02.006

Cited by 53 publications

(37 citation statements)

References 63 publications

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“…The reaction advancement was tracked by TLC. Furthermore, treatment of 15 with DMF and triethylamine resulted in the cyclization of 15 and furnished the correspond- (14) in moderate yield, as shown in Scheme 7. The elucidation of compound 14 was concentrated on its spectral…”

Section: Resultsmentioning

confidence: 99%

“…In this letter, we have developed an unprecedented, original two-component, one-pot approach for the synthesis of highly substituted methine cyanine dyes 3,6,7,8,9,10,11,12,14 …”

Section: Resultsmentioning

confidence: 99%

“…Yield 43%; violet crystals; m.p. > 300 C; IR (KBr): y/cm À1 ¼ thiadiazol-2(3H)-ylidene) (phenyl)methyl)]bis-pyridinium dibromide (14). Pathway 1.…”

Section: Resultsmentioning

confidence: 99%

“…10 With the growth of relative technologies, methine cyanine dyes have been screened as tools in photodynamic treatment 11 and as uorescent labels, micelles, organelles and probes for cells. [12][13][14][15] Usually, mono and dimethine cyanines are synthesized by heating a mixture of aromatic aldehydes, a quaternary ammonium salt with an active methyl group and a catalyst agent in an organic environment under reux. 16 This synthesis has intrinsic obstacles as relatively the reaction requires relatively energetic conditions, namely heating with reux reactants for diverse hours in solvents, many organic solvents inimical to environment and complexity in product isolation.…”

Section: Introductionmentioning

confidence: 99%

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Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

El‐Mekawy

Fadda

2017

RSC Adv.

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In this study, we have introduced an outlook dealing with synthetic heteroarenium-substituted pyridines 1 that are suitable as starting materials for the synthesis of a potential new thiocarbamoyl derivative 3 that may be of value in preparative organic and biological chemistry. Herein, a new series of twelve bis-mono and dimethine cyanine dyes incorporating different heterocyclic compounds were designed by efficient and simple reaction of compound 3 with various organic reagents to overcome the obstacles of energetic reactions, because they took long times. Moreover, the electronic behaviors of these compounds were studied because of their significant activity in many medical and other fields. The photosensitizers were elucidated by spectral and analytical analyses.

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Section: Resultsmentioning

confidence: 99%

“…In this letter, we have developed an unprecedented, original two-component, one-pot approach for the synthesis of highly substituted methine cyanine dyes 3,6,7,8,9,10,11,12,14 …”

Section: Resultsmentioning

confidence: 99%

“…Yield 43%; violet crystals; m.p. > 300 C; IR (KBr): y/cm À1 ¼ thiadiazol-2(3H)-ylidene) (phenyl)methyl)]bis-pyridinium dibromide (14). Pathway 1.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

El‐Mekawy

Fadda

2017

RSC Adv.

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“…2 Recently, methine cyanine dyes have attracted attention owing to their excellent fluorescence properties [3][4][5] as well as their potential applications in probes for DNA in living cells. [6][7][8][9][10] From the applications of cyanine dyes it is known that the optical properties of cyanine dyes are often influenced by their conjugated systems and the solution environment. Trinucleus dimethine cyanine dyes are large conjugated systems, which contain three heteroaromatic rings joined by two vinyl chains.…”

Section: Introductionmentioning

confidence: 99%

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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Design, Synthesis and Biological Evaluation of Trimethine Cyanine Dyes as Fluorescent Probes for the Detection of Tau Fibrils in Alzheimer’s Disease Brain and Olfactory Epithelium

Anumala

Haußen

et al. 2013

ChemMedChem

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Syntheses and DNA-binding studies of a series of unsymmetrical cyanine dyes: structural influence on the degree of minor groove binding to natural DNA

Cited by 53 publications

References 63 publications

Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

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

Design, Synthesis and Biological Evaluation of Trimethine Cyanine Dyes as Fluorescent Probes for the Detection of Tau Fibrils in Alzheimer’s Disease Brain and Olfactory Epithelium

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