Benzothiazole-substituted benzofuroquinolinium dye: a selective switch-on fluorescent probe for G-quadruplex

Lu, Yu; Yan, Siu‐Cheong; Chan, Fung‐Yi; Zou, Li; Chung, Wai Hong; Wong, Wing Leung; Qiu, Bin; Sun, Ning; Chan, P.H.; Huang, Zifang; Gu, Lian Quan

doi:10.1039/c1cc00020a

Cited by 70 publications

(41 citation statements)

References 31 publications

(9 reference statements)

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“…E. coli BL21(DE3) cells were transformed with the pRSET-A-S vector carrying S. aureus FtsZ with a 6-histidine tag attached at its N-terminus under the control of a T7 promoter [37]. The transformed E. coli strain was streaked on a nutrient agar plate containing 50 µg/mL ampicillin, and the agar plate was incubated at 37°C overnight.…”

Section: Methodsmentioning

confidence: 99%

Rational Design of Berberine-Based FtsZ Inhibitors with Broad-Spectrum Antibacterial Activity

Sun

Chan

et al. 2014

PLoS ONE

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Inhibition of the functional activity of Filamenting temperature-sensitive mutant Z (FtsZ) protein, an essential and highly conserved bacterial cytokinesis protein, is a promising approach for the development of a new class of antibacterial agents. Berberine, a benzylisoquinoline alkaloid widely used in traditional Chinese and native American medicines for its antimicrobial properties, has been recently reported to inhibit FtsZ. Using a combination of in silico structure-based design and in vitro biological assays, 9-phenoxyalkyl berberine derivatives were identified as potent FtsZ inhibitors. Compared to the parent compound berberine, the derivatives showed a significant enhancement of antibacterial activity against clinically relevant bacteria, and an improved potency against the GTPase activity and polymerization of FtsZ. The most potent compound 2 strongly inhibited the proliferation of Gram-positive bacteria, including methicillin-resistant S. aureus and vancomycin-resistant E. faecium, with MIC values between 2 and 4 µg/mL, and was active against the Gram-negative E. coli and K. pneumoniae, with MIC values of 32 and 64 µg/mL respectively. The compound perturbed the formation of cytokinetic Z-ring in E. coli. Also, the compound interfered with in vitro polymerization of S. aureus FtsZ. Taken together, the chemical modification of berberine with 9-phenoxyalkyl substituent groups greatly improved the antibacterial activity via targeting FtsZ.

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Section: Methodsmentioning

confidence: 99%

Rational Design of Berberine-Based FtsZ Inhibitors with Broad-Spectrum Antibacterial Activity

Sun

Chan

et al. 2014

PLoS ONE

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“…By following a similar strategy, Wong and co-workers fused a natural product benzofuroquinolinium moiety with Thiazole Orange to give a benzofuroquinolonium-benzathiazole hybrid (30). [203] This compound also exhibited very impressive G-quadruplex selectivity and fluorescence enhancement compared to duplex DNA. When applied to fixed cells, it showed intense staining of nucleoli.…”

Section: Classic Groove Bindersmentioning

confidence: 99%

Fluorescent Probes for G‐Quadruplex Structures

2013

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Mounting evidence supports the presence of biologically relevant G-quadruplexes in single-cell organisms, but the existence of endogenous G-quadruplex structures in mammalian cells remains highly controversial. This is due, in part, to the common misconception that DNA and RNA molecules are passive information carriers with relatively little structural or functional complexity. For those working in the field, however, the lack of available tools for characterizing DNA structures in vivo remains a major limitation to addressing fundamental questions about structure-function relationships of nucleic acids. In this review, we present progress towards the direct detection of G-quadruplex structures by using small molecules and modified oligonucleotides as fluorescent probes. While most development has focused on cell-permeable probes that selectively bind to G-quadruplex structures with high affinity, these same probes can induce G-quadruplex folding, thereby making the native conformation of the DNA or RNA molecule (i.e., in the absence of probe) uncertain. For this reason, modified oligonucleotides and fluorescent base analogues that serve as "internal" fluorescent probes are presented as an orthogonal means for detecting conformational changes, without necessarily perturbing the equilibria between G-quadruplex, single-stranded, and duplex DNA. The major challenges and motivation for the development of fluorescent probes for G-quadruplex structures are presented, along with a summary of the key photophysical, biophysical, and biological properties of reported examples.

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“…[13] Recently, a chemosensor has been presented that enables the fluorimetric differentiation of quadruplex DNA from other nucleic acids in cells. [14] Moreover, it has been shown that the fluorimetric discrimination of regions with different polarities may be accomplished in cells with quinoxaline derivatives. [15] Along these lines, the use of near-infrared (NIR, 650-900 nm) fluorescent probes is advantageous for biological applications, because NIR fluorophores exhibit low or almost no phototoxicity, relatively deep penetration into tissue, and negligible interference with the autofluorescence of cells.…”

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confidence: 99%

9‐(4‐Dimethylaminophenyl)benzo[b]quinolizinium: A Near‐Infrared Fluorophore for the Multicolor Analysis of Proteins and Nucleic Acids in Living Cells

Bortolozzi

Ihmels

Thomas

et al. 2013

Chemistry A European J

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Benzothiazole-substituted benzofuroquinolinium dye: a selective switch-on fluorescent probe for G-quadruplex

Cited by 70 publications

References 31 publications

Rational Design of Berberine-Based FtsZ Inhibitors with Broad-Spectrum Antibacterial Activity

Rational Design of Berberine-Based FtsZ Inhibitors with Broad-Spectrum Antibacterial Activity

Fluorescent Probes for G‐Quadruplex Structures

9‐(4‐Dimethylaminophenyl)benzo[b]quinolizinium: A Near‐Infrared Fluorophore for the Multicolor Analysis of Proteins and Nucleic Acids in Living Cells

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