Boosting the turn-on fluorescent signaling ability of thiazole orange dyes: The effectiveness of structural modification site and its unusual interaction behavior with nucleic acids

Long, Wei; Lu, Yu‐Jing; Zhang, Kun; Huang, Xuan-He; Hou, Jinqiang; Cai, Sen-Yuan; Liu, Ying; Du, Xian; Luyt, Leonard G.; Wong, Wing‐Leung; Chow, Cheuk Fai Stephen

doi:10.1016/j.dyepig.2018.07.008

Cited by 17 publications

(16 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…YO is like TO, having a high enhancement of quantum yield after binding to DNA. The molecular structures of TO and YO often undergo modifications to achieve higher sensitivity, photostability, or imaging of bioactivity in living cells [83] . Both TO and YO derivatives usually have quite low fluorescence, but become strongly fluorescent with high quantum yield after binding to biomolecules [84] …”

Section: Optical Properties and Applications Of Cyanine Dyes Containimentioning

confidence: 99%

Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

Ilina

Henary

2020

Chemistry A European J

View full text Add to dashboard Cite

Cyanine dyes carrying quinoline moieties are an important class of organic molecules that are of great interest for applications in many fields like medicine, pharmacology, and engineering. Despite their exceptional properties, such as stability, high molar extinction coefficients, and high pH‐sensitivity, this class of dyes has been less analyzed and reviewed in the last few decades. Therefore, this review article focuses on discussing the history of quinoline compounds, various synthetic routes to prepare quinolinium salts and symmetrical and asymmetrical mono‐, di‐, tri‐, penta‐ and heptamethine cyanine dyes, containing quinoline moieties, together with their optical properties and applications as photosensitizers in photodynamic therapy, probes in biomolecules for labeling of nucleic acids, as well as imaging agents.

show abstract

Section: Optical Properties and Applications Of Cyanine Dyes Containimentioning

confidence: 99%

Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

Ilina

Henary

2020

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Figure a shows a larger Δ T m value (5°C) for F21T than that of a duplex DNA (F10T, Δ T m = 0.5°C) at concentration of at 2 μM of 1 . This is probably due to the compound possessing three amino terminal groups that are able to enhance the interactions with G‐quadruplex . Moreover, circular dichroism (CD) spectroscopy was applied to acquire more information about the interaction property and conformation influence of 1 on telo21.…”

Section: Resultsmentioning

confidence: 99%

A propeller‐like small molecule as a novel G‐quadruplex DNA binder: The study of fluorescent sensing property and preferential interactions with human telo21 structure

Sun

Hou

et al. 2018

Chem Biol Drug Des

Self Cite

View full text Add to dashboard Cite

A new propeller-like small molecule was synthesized with three terminal amino side groups. The molecule was found to be a selective nucleic acid binder towards telo21 G-quadruplex DNA compared with other representative nucleic acids including single-stranded DNA (dA21), duplex DNA (ds26) and RNA. The fluorescent signal of the molecule upon interaction with telo21 G-quadruplex structure shows remarkable enhancement (F /F = 17.9) while interaction with other nucleic acids shows the signal enhancement which is less than 2.1. In addition, a good linear relationship of binding signal correlated with the concentration of telo21 DNA was obtained. Molecular docking study was also performed to acquire the binding behaviour and its interaction modes of the molecule with the structure of human telomeric DNA G-quadruplex. The modelling results show that the three conjugated terminal units (dimethylaminobenzyl groups) associated through the ethylene bridges with the central methylated pyridine ring formed a co-planar conformation upon stacking onto the G-quartets via pi-pi stacking interactions. This could be the key reason that the molecule shows excellent fluorescent signal of binding towards telo21 G-quadruplex DNA rather than other types of nucleic acids.

show abstract

“…The new thiazole-quinolinium derivatives (4a-e) shown in Table 1 were prepared in good yields by following the reported procedures 20,21 (Scheme 1). Intermediates 3a and 3b were obtained by the reaction of 1,2-dimethyl-4-chloroquinolinium iodide or N-methyl-4-chloroquinolinium with N-(3-bromopropyl)-2-methylbenzo[d]thiazolium iodide in the presence of sodium bicarbonate.…”

Section: Design and Synthesis Of The Thiazole-quinolinium Derivativesmentioning

confidence: 99%

“…The synthesis of intermediates 1a, 1b and 2 was followed the reported methods. 21 Compounds 4a2, 4b1 and 4b2 were reported as the uorescent bio-molecular sensors. 21…”

Section: Design and Synthesis Of The Thiazole-quinolinium Derivativesmentioning

confidence: 99%

Antibacterial activity evaluation and mode of action study of novel thiazole-quinolinium derivatives

Sun

Ser

et al. 2020

RSC Adv.

Self Cite

View full text Add to dashboard Cite

show abstract

Boosting the turn-on fluorescent signaling ability of thiazole orange dyes: The effectiveness of structural modification site and its unusual interaction behavior with nucleic acids

Cited by 17 publications

References 58 publications

Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

A propeller‐like small molecule as a novel G‐quadruplex DNA binder: The study of fluorescent sensing property and preferential interactions with human telo21 structure

Antibacterial activity evaluation and mode of action study of novel thiazole-quinolinium derivatives

Contact Info

Product

Resources

About