Synthesis of chloro-substituted analogs of Thiazole orange – Fluorophores for flow cytometric analyses

Kaloyanova, Stefka; Иванова, И. А.; Tchorbanov, Andrey; Dimitrova, Petya; Deligeorgiev, Todor

doi:10.1016/j.jphotobiol.2011.03.012

Cited by 9 publications

(9 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The nucleic acid-intercalating moiety of TOMA, an analog of thiazole orange, provides a practical method to visualize the mitochondria of living cells using a variety of observation wavelengths with excitation in the visible range and can be used for probing living cells (Carreon, Stewart, Mahon, Shin, & Kelley, 2007). Another study showed that several chloro-containing analogs of thiazole orange had good specificity for DNA and can be successfully used for flow cytometric analyses of DNA contents in live cells (Kaloyanova, Ivanova, Tchorbanov, Dimitrova, & Deligeorgiev, 2011). The nucleic acid-intercalating moiety of TOMA also belongs to asymmetrical monomethine cyanine dye that has been proven to be useful probes for live cellular imaging and highly selective for DNA binding (Kaloyanova et al, 2011), which provides a theoretical basis of TOMA for detection of viable cells.…”

Section: Discussionmentioning

confidence: 99%

“…Another study showed that several chloro-containing analogs of thiazole orange had good specificity for DNA and can be successfully used for flow cytometric analyses of DNA contents in live cells (Kaloyanova, Ivanova, Tchorbanov, Dimitrova, & Deligeorgiev, 2011). The nucleic acid-intercalating moiety of TOMA also belongs to asymmetrical monomethine cyanine dye that has been proven to be useful probes for live cellular imaging and highly selective for DNA binding (Kaloyanova et al, 2011), which provides a theoretical basis of TOMA for detection of viable cells.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Molecular monitoring of disinfection efficacy of E. coli O157:H7 in bottled purified drinking water by quantitative PCR with a novel dye

Cao

Zhou²,

et al. 2019

J Food Process Preserv

View full text Add to dashboard Cite

A new method was developed using a novel dye thiazole orange monoazide (TOMA) combined with quantitative real‐time PCR (qPCR) to detect viable Escherichia coli O157:H7 cells. Different from the commonly used PMA‐qPCR assay that is based on membrane integrity, this TOMA‐qPCR method is based on the concept of metabolic activity. TOMA consists of three components: a nucleic acid‐intercalating moiety, a crosslinkable moiety and a linker. TOMA concentration at 50 μg/ml, 20 min incubation time, and 30 min light exposure time were suggested to use for detecting viable cells. When the inoculum concentration was 103 CFU/100 ml, TOMA‐qPCR assay could completely exclude the effect of dead cells treated with heat, chlorine, or UV. Moreover, TOMA‐qPCR could also be used to detect viable but nonculturable state (VBNC) cells. The result shows that TOMA‐qPCR would be an alternative choice for the detection of viable cells. Practical applications To specifically detect only viable cells is of great importance in most detection of microbial diagnostics, especially for detection of foodborne pathogens such as E. coli O157:H7, which could cause health risk at low concentrations. The existing detection methods have some defects in detecting only viable cells. In this article, a novel dye was developed and combined with qPCR, to monitor sanitizing efficacy of different disinfection methods on E. coli O157:H7 at low concentrations. When detecting viable E. coli in bottled water, the established TOMA‐qPCR assay completely exclude the effect of dead cells when the inoculated concentration is 103 CFU/100 ml. This method is also suitable for the detection of VBNC samples. Therefore, this method can be used to detect pathogenic bacteria with low contamination under extreme conditions such as low temperature, oligotrophic, strong radiation, and so on.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Molecular monitoring of disinfection efficacy of E. coli O157:H7 in bottled purified drinking water by quantitative PCR with a novel dye

Cao

Zhou²,

et al. 2019

J Food Process Preserv

View full text Add to dashboard Cite

show abstract

“…Visualization of compounds was achieved by illumination under ultraviolet light (254 nm). Compounds ethyl 2,2-diethoxypropanoate 8 , 15 , 16 , 21 , 22 , and 24 were prepared according to the literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Solution Aggregation Studies of a Suite of Mixed Neutral and Zwitterionic Chromophores for Second-Order Nonlinear Optics

et al. 2014

View full text Add to dashboard Cite

We report details of the synthesis of a series of bi- and trichromophores. These compounds contain mixtures of chromophores that have zwitterionic (ZWI) and neutral ground state (NGS) components covalently attached to each other. The neutral ground state moieties are based on dyes with aniline donors--such as Disperse Red 1--whereas the zwitterionic components are derived from chromophores with pro-aromatic donors such as 1,4-dihydropyridinylidene. By combining both ZWI and NGS components, we aim to develop novel compounds for nonlinear optics in which there is an enhancement of the overall hyperpolarizability coupled with a decrease in the net dipole moment. Thus, this approach should eliminate the electrostatic effects that result when only one type of chromophore is used, and so reduce the likelihood of undesirable aggregation occurring. This, in turn, should enable us to realize organic materials with large macroscopic optical nonlinearities. An analysis of the UV-vis results suggests that there is a strong dependence on solvent polarity that determines whether the embedded constituents should be treated as discrete elements; in low polarity solvents, there appear to be strong intramolecular interactions occurring, particularly when a 1,4-quinolinylidene-based donor is used in the ZWI component.

show abstract

“…A series of eight asymmetric cyanine dyes (Scheme 1) were modelled with the help of DFT and TDDFT calculations to gather deep insights into the geometry and electron density distribution in the ground and excited states and to achieve a better understanding of the electronic spectra of the dyes. The cyanine dyes that were used in the present study were previously synthesized by our group [18,57,58]. The geometries of the cis-and trans-TO conformers optimized at the B3LYP/6-31G(d,p) theory levels are presented in Figure 1.…”

Section: Geometry Optimizationmentioning

confidence: 99%

Theoretical Modeling of Absorption and Fluorescent Characteristics of Cyanine Dyes

et al. 2022

View full text Add to dashboard Cite

The rational design of cyanine dyes for the fine-tuning of their photophysical properties undoubtedly requires theoretical considerations for understanding and predicting their absorption and fluorescence characteristics. The present study aims to assess the applicability and accuracy of several DFT functionals for calculating the absorption and fluorescence maxima of monomethine cyanine dyes. Ten DFT functionals and different basis sets were examined to select the proper theoretical model for calculating the electronic transitions of eight representative molecules from this class of compounds. The self-aggregation of the dyes was also considered. The pure exchange functionals (M06L, HFS, HFB, B97D) combined with the triple-zeta basis set 6-311+G(2d,p) showed the best performance during the theoretical estimation of the absorption and fluorescent characteristics of cyanine dyes.

show abstract

Synthesis of chloro-substituted analogs of Thiazole orange – Fluorophores for flow cytometric analyses

Cited by 9 publications

References 16 publications

Molecular monitoring of disinfection efficacy of E. coli O157:H7 in bottled purified drinking water by quantitative PCR with a novel dye

Molecular monitoring of disinfection efficacy of E. coli O157:H7 in bottled purified drinking water by quantitative PCR with a novel dye

Synthesis and Solution Aggregation Studies of a Suite of Mixed Neutral and Zwitterionic Chromophores for Second-Order Nonlinear Optics

Theoretical Modeling of Absorption and Fluorescent Characteristics of Cyanine Dyes

Contact Info

Product

Resources

About