Synthesis of homodimeric monomethine cyanine dyes as noncovalent nucleic acid labels and their absorption and fluorescence spectral characteristics

Deligeorgiev, Todor; Gadjev, Nikolai; Timtcheva, I.; Maximova, Vera; Katerinopoulos, Haralambos E.; Foukaraki, Evangelia

doi:10.1016/s0143-7208(99)00084-4

Cited by 38 publications

(19 citation statements)

References 9 publications

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“…As with squarylium dyes, the fluorescence efficiency of the conformationally flexible cyanine counterparts is greatly enhanced upon immobilization in complexes with biomolecules. Polycationic cyanine derivatives including 9-11 have been synthesized for a strong binding to nucleic acids [19][20][21][22][23][24][25]. On the other hand, dyes 12-14 with a net charge of -1 show strong interaction with proteins [26][27][28][29][30].…”

Section: Cyanine Dyesmentioning

confidence: 99%

“…In the presence of ds DNA the Stokes' shifts of about 30 nm and the fluorescence quantum yields in the range 0.48-0.96 have been observed. These homodimers are bisintercalators with selectivity toward the 5'-CTGAG-3' binding site of oligonucleotides [21,24,25]. Interestingly, compound 10 and analogs also bind strongly with singlestranded (ss) DNA.…”

Section: Cyanine Dyesmentioning

confidence: 99%

“…Interestingly, compound 10 and analogs also bind strongly with singlestranded (ss) DNA. In the complexes with ss DNA they also fluoresce strongly with quantum yields in the range 0.3-0.8 [21]. The isoxazolium homodimer 11 is less valuable for noncovalent labeling of DNA due to hypsochromically shifted absorption relative to that of 10 [22].…”

Section: Cyanine Dyesmentioning

confidence: 99%

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Noncovalent Labeling of Biomolecules with Red and Near- Infrared Dyes

et al. 2004

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Biopolymers such as proteins and nucleic acids can be labeled with a fluorescent marker to allow for their detection. Covalent labeling is achieved by the reaction of an appropriately functionalized dye marker with a reactive group on a biomolecule. The recent trend, however, is the use of noncovalent labeling that results from strong hydrophobic and/or ionic interactions between the marker and biomolecule of interest. The main advantage of noncovalent labeling is that it affects the functional activity of the biomolecule to a lesser extent. The applications of luminescent cyanine and squarylium dyes are reviewed.

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Section: Cyanine Dyesmentioning

confidence: 99%

Section: Cyanine Dyesmentioning

confidence: 99%

Section: Cyanine Dyesmentioning

confidence: 99%

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Noncovalent Labeling of Biomolecules with Red and Near- Infrared Dyes

et al. 2004

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“…Binding with nitrogen bases enhances the fluorescence intensity of the probe compared to the free molecule (in solution), and this property of FP is widely used in various fields of molecular biology and biochemistry. Tetra cationic bis-intercalators cyanine dyes; 1- Figure 1) and their analogues occupy the most important class among bisintercalating dyes (4,5). They have a higher affinity to DNA than mono-intercalators dicationic thiazole orange (TO) (6,7), since these bis-intercalators contain two intercalating groups.…”

Section: Introductionmentioning

confidence: 99%

“…According to the classical method, bis-intercalating ТОТО families were synthesized by the reaction of the monomethine dye containing a haloalkyl group with tertiary diamine linkers in DMF for 12 h as minimum (5,(28)(29)(30)(31)(32)(33). In some cases, the reaction required long time and may exceed 3 days followed by the addition of methanol and keeping of the reaction mixture at 0°C and in this case, the yield of the product does not exceed 25% (3).…”

Section: Introductionmentioning

confidence: 99%

Microwave synthesis and fluorescence properties of homo- and heterodimeric monomethine cyanine dyes TOTO and their precursors

Alganzory

El‐Sayed

Arief

et al. 2016

Green Chemistry Letters and Reviews

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A series of monomeric and dimeric cyanine dyes belonging to the thiazole orange family have been prepared via an improved synthetic procedure, by the reaction of the monomethine dye containing an iodoalkyl group with tertiary diamine linkers under microwave irradiation. The effects of microwave power and irradiation time on yield were examined. The electronic absorption and steady-state fluorescence spectra of prepared dyes have been investigated. Fluorescence properties indicate significance in singlet oxygen sensitization and make the present compounds potential candidates in the area of photodynamic therapy. ARTICLE HISTORY

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Mono‐ and bis‐intercalating dyes for multiplex fluorescence lifetime detection of DNA restriction fragments in capillary electrophoresis

et al. 2002

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The use of novel intercalating dyes as labels in DNA restriction fragment analysis by capillary electrophoresis with frequency-domain fluorescence lifetime detection is described. The dyes, including one mono-intercalating dye with three positive charges and three bis-intercalating, homodimeric dyes with four positive charges, were excited by the 488 nm line of an argon ion laser and exhibited lifetimes in the range of 1-3 ns. The separations were performed using a gel containing 1% high-molecular-weight (HMW) hydroxyethylcellulose (HEC) (90,000-105,000) and 0.3% low-molecular-weight (LMW) HEC (24,000-27,000) in Tris-borate-EDTA buffer (TBE). Multiplex lifetime detection of mixtures of dye-labeled DNA restriction fragment digests and size standard fragments was achieved. Compared to previous results obtained with several mono-intercalating dyes of lesser charge (McIntosh, S. L., Nunnally, B. K., Nesbit, A. R., Deligeorgiev, T. G., Gadjev, N. I., McGown, L. B., Anal. Chem. 2000, 72, 5444-5449), the present dyes provided a wider range of lifetimes and better lifetime discrimination in multiplex detection. There was no evidence of dye exchange during the capillary electrophoresis experiment.

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Synthesis of homodimeric monomethine cyanine dyes as noncovalent nucleic acid labels and their absorption and fluorescence spectral characteristics

Cited by 38 publications

References 9 publications

Noncovalent Labeling of Biomolecules with Red and Near- Infrared Dyes

Noncovalent Labeling of Biomolecules with Red and Near- Infrared Dyes

Microwave synthesis and fluorescence properties of homo- and heterodimeric monomethine cyanine dyes TOTO and their precursors

Mono‐ and bis‐intercalating dyes for multiplex fluorescence lifetime detection of DNA restriction fragments in capillary electrophoresis

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