New asymmetric monomethine cyanine dyes for nucleic-acid labelling: absorption and fluorescence spectral characteristics

Timtcheva, I.; Maximova, Vera; Deligeorgiev, Todor; Zaneva, D.; Ivanov, Ivan B.

doi:10.1016/s1010-6030(99)00207-5

Cited by 68 publications

(46 citation statements)

References 10 publications

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“…A considerable decrease in the absorption of the compound and a weak red shift of the spectra was observed when DNA was added. As reported, a hypochromic effect and blue shift of the absorption spectra are signs of external binding, while a red shift and of the spectra is a sign of intercalation (Dourlent and Hélène, 1971;Long and Barton, 1990;Timtcheva et al, 2000). It can be seen from Figure 2 that MIDBT had strong absorption peaks at 285 nm and 355 nm.…”

Section: The Interaction Of Midbt With Dna Determined By Uv-vissupporting

confidence: 55%

Cytotoxic Activities and DNA Binding Properties of 1-Methyl-7H-indeno[1,2-b]Quinolinium-7-(4-dimethylamino) Benzylidene Triflate

Wen

Wang

et al. 2012

DNA and Cell Biology

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The interaction of calf thymus DNA (ct-DNA) with a novel synthesized pyrazolo [1,5-a]indole compound 1-methyl-7H-indeno[1,2-b]quinolinium-7-(4-dimethylamino) benzylidene triflate (MIDBT) was extensively studied by various spectroscopic techniques, viscosity measurements, and gel electrophoresis. The UV-visible observation implied that the compound interacted with ct-DNA by two binding modes, intercalating into the DNA base pairs and attaching to the helix exterior of DNA. The results of the fluorescent quenching and viscosity measurements showed that MIDBT could intercalate into DNA base pairs deeply in a classical intercalative mode. Circular dichroism results showed that the binding of MIDBT shifted ct-DNA conformation from B to A at low concentrations. In the gel electrophoresis, the compound was found to promote the cleavage of plasmid pBR 322 DNA effectively. Furthermore, cytotoxic studies of this compound against eleven selected tumor cell lines have been done. The values of 50% cytotoxic concentration (IC 50 ) were in the range of 1.09-18.84 mM, exhibiting the potent cytotoxic properties.

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Section: The Interaction Of Midbt With Dna Determined By Uv-vissupporting

confidence: 55%

Cytotoxic Activities and DNA Binding Properties of 1-Methyl-7H-indeno[1,2-b]Quinolinium-7-(4-dimethylamino) Benzylidene Triflate

Wen

Wang

et al. 2012

DNA and Cell Biology

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“…5 Thiazole ring is an important pharmacophore and its coupling with other rings could furnish new biologically active compounds 6 which exhibit a wide range of biological properties, such as antitumor, anticonvulsant, 7 cardiotonic, 8 IMP dehydrogenase inhibiton, 10 analgesics, 10 anticancer. 11 Thiazole ring also finds applications in other fields, such as polymers, 12 liquid crystals, 13 photonucleases, 14 fluorescent dyes, 15,16 insecticides 17 and antioxidant [18]. Furthermore, 1,3-thiazole and 1,3-benzothiazoles possess important biological properties such as distinctive antifungal, antimicrobial, antitubercular, anticancer, anti-angiogenic, antiproliferative and cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, in vitro antiproliferative and cytotoxicity effects of a new class of 2-((1R,2S)-2-((E)-4-substitutedstyryl) cyclooctyl)benzo[d]thiazole derivatives

Uremis¹,

Yağlıoğlu²,

Budak³

et al. 2017

Org. Commun.

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Abstract:The novel 2-((1R,2S)-2-((E)-4-substitutedstyryl) cyclooctyl)benzo [d]thiazoles (12-14) were synthesized from the reaction of 10-(4-substitutedbenzylidene)bicyclo[6.2.0]decan-9-ones (5a-8a) with 2-aminothiophenol (11) in the presence of p-TsOH at reflux conditions in good yields. The antiproliferative activities of 12-14 were determined againts C6 (rat brain carcinoma) and HeLa (human cervical carcinoma) cell lines using BrdU cell proliferation ELISA assay. 5-Fu (5-fluorouracil) was used as standard. The antiproliferative activities of 12-14 and the control were investigated on eight concentrations (5, 10, 20, 30, 40, 50, 75 and 100 µM). The results showed that the synthesized compounds had significant antiproliferative activity and low cytotoxicity effects.

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“…[2][3][4][5][6] Recently, based on Tf can specifically recognized Tf receptor, Tf has been exploited as a potential strategy of drug to deliver drugs, which are loaded by either covalent conjugation or noncovalent binding, targeting cancer cells with over-expressed Tf receptors on its surface. [7] Meanwhile, cyanine dyes as fluorescent probes for labeling biological systems have attracted considerable attention because of their special properties [8][9][10][11] -wide spectral range, high fluorescence quantum yield, and high molar extinction. And their regulatory structure and a variety of state of aggregation are critical to bind with biomolecules.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Investigation on the Binding of a Cyanine Dye with Transferrin

Zhang

Ling

Chen

et al. 2015

J. Phys. Org. Chem.

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Transferrin (Tf) can control the level of free iron as iron-binding blood plasma glycoprotein in biological fluids. Tf has been exploited in the recent years on account of the potential function as a drug carrier targeting to tumor cells. Cyanine dyes have been widely studied as photosensitizers. The binding mechanism of Tf with 3, 3′-di(3-sulfopropyl)-4, 5, 4′, 5′-dibenzo-9-ethyl-thiacarbocyanine triethylammonium salt (ETC) was characterized at varying pHs and temperatures by fluorescence, UV-Vis absorption, circular dichroism (CD), and molecular modeling methods. The results showed that the static fluorescence quenching occurred between Tf and ETC. It was found that ETC bound strongly with Tf with an intrinsic binding constant (K a ), in the order of 10 7 MÀ1 . The thermodynamic parameters demonstrated that van der Waals force or hydrogen bonds were the major binding force. The binding of ETC-Tf caused the secondary conformational change of Tf with increasing the α-helix content in Tf, which was confirmed by the results of spectroscopic experiments. Molecular modeling revealed that ETC bound residues located in the N-lobe of Tf by van der Waals force and induced local structural changes of Tf. This study may provide the theoretical foundations for ETC as a probe to label Tf, which is further beneficial to the Tf-targeted drugs in vivo.

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New asymmetric monomethine cyanine dyes for nucleic-acid labelling: absorption and fluorescence spectral characteristics

Cited by 68 publications

References 10 publications

Cytotoxic Activities and DNA Binding Properties of 1-Methyl-7H-indeno[1,2-b]Quinolinium-7-(4-dimethylamino) Benzylidene Triflate

Cytotoxic Activities and DNA Binding Properties of 1-Methyl-7H-indeno[1,2-b]Quinolinium-7-(4-dimethylamino) Benzylidene Triflate

Synthesis, characterization, in vitro antiproliferative and cytotoxicity effects of a new class of 2-((1R,2S)-2-((E)-4-substitutedstyryl) cyclooctyl)benzo[d]thiazole derivatives

Spectroscopic Investigation on the Binding of a Cyanine Dye with Transferrin

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