Enantioselective binding of S- and R-ofloxacin to various synthetic polynucleotides

Hwangbo, Hyǔn Jung; Yun, Byeong Hwa; Soon, Jin; Kwon, Dae Young; Kim, Seog K.

doi:10.1016/s0928-0987(02)00279-8

Cited by 25 publications

(17 citation statements)

References 13 publications

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“…The appearance of the ICD of optically inactive molecules or changes in the intrinsic CD of chiral molecule reflects the binding geometry and binding mode of the molecule as well as the arrangements of neighboring DNA bases [12]. Our results suggest that CAT can interact in a concentration-dependent manner with double-helical DNA, and the interactions were later proved to be intercalating by viscosity measurements.…”

Section: Discussionmentioning

confidence: 78%

“…Fluorescence emission spectra are sensitive to changes in the fluorophore’s environment such as polarity and the presence of quencher [12]. Fluorescence emission spectra were recorded for CAT in the presence and absence of DNA with a 260-nm excitation.…”

Section: Resultsmentioning

confidence: 99%

“…Concentration-dependent interactions between this compound and DNA were observed in DNA solution by circular dichroism (CD) [10] and fluorescence emission spectra [11,12]. What is of great significance is that this compound seemed to interact in a sequence-specific manner with an AT-repeated sequence of double-helical DNA and this is, to the best of our knowledge, the first time a phenanthroindolizidine alkaloid was found to have sequence-specific interactions with duplex DNA.…”

Section: Introductionmentioning

confidence: 99%

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Interaction Studies of an Anticancer Alkaloid, (+)-(13aS)-Deoxytylophorinine, with Calf Thymus DNA and Four Repeated Double-Helical DNAs

Liu¹,

Li³

et al. 2011

Chemotherapy

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Background: Phenanthroindolizidine alkaloids are a family of plant-derived compounds with significant antineoplastic activity. The specific biomolecular targets of these alkaloids have not yet been clearly identified. (+)-(13aS)-deoxytylophorinine is a new phenanthroindolizidine alkaloid originally extracted from the roots of Tylophora atrofolliculata and Tylophora ovata in our institute. (+)-(13aS)-deoxytylophorinine exerts both in vitro and in vivoanticancer activities. Methods: The in vivo anticancer effects and toxicity of this compound were investigated in mice, and interactions between this compound and double-helical DNA sequences were studied in detail with circular dichroic spectroscopy and fluorescence spectroscopy. Viscosity measurements were applied to check the interactive mode between this compound and DNA. Results: Potent anticancer effects were observed in vivo. Also, concentration-dependent interactions were observed and this compound seemed to interact in a sequence-specific manner with AT-repeated sequences of double-helical DNA. Such interactions were proved to be intercalating by viscosity measurements. Conclusions: Anticancer alkaloid (+)-(13aS)-deoxytylophorinine can have sequence-specific interactions with DNA in an intercalating manner.

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Section: Discussionmentioning

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Interaction Studies of an Anticancer Alkaloid, (+)-(13aS)-Deoxytylophorinine, with Calf Thymus DNA and Four Repeated Double-Helical DNAs

Liu¹,

Li³

et al. 2011

Chemotherapy

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“…Alternatively, microbial and immunoassay tools have been developed [1,[14][15][16][17]. Studies on biosensors have been accomplished as other alternatives [18][19][20] such as a biosensor using DNA and gyrase which are broad selective acceptors for fluoroquinolone as well as enrofloxacin [18].…”

Section: Introductionmentioning

confidence: 99%

Immuno-strip biosensor system to detect enrofloxacin residues

Kim

2009

Journal of Industrial and Engineering Chemistry

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“…1), a member of the quinolone antibiotics, which exhibits antibacterial activity by inhibiting the action of Type II topoisomerase, was originally proposed to bind to DNA molecules. [10][11][12][13] Previous studies have shown that the enantioselective discrimination of short duplexes (10~22 bp) toward S-ofloxacin against R-ofloxacin was attributed to the steric hindrance between the methyl group of ofloxacin and the phosphate backbone of DNA. Interestingly, a distinct discrimination mechanism was involved in the enantioselective recognition of ofloxacin enantiomers between GC-and AT-rich oligonucleotides.…”

mentioning

confidence: 99%

Intrinsic Enantioselectivity of Natural Polynucleotides Modulated by Copper Ions

Chen

Zhang

et al. 2015

Chirality

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Natural polynucleotides including Micrococcus lysodeikticus and calf thymus DNA exhibit enantioselective recognition to S-ofloxacin regulated by Cu(2+). This is the first report that ofloxacin and Cu(2+) have cooperative effects on the local distortions of polynucleotides. At the [Cu(2+)]/[base] ratio of 0.1, S-ofloxacin is more liable to induce the locally distorted structures of polynucleotides, of which the association constant of S-ofloxacin toward DNA-Cu(II) is three times higher than that of the R-enantiomer. The apparent increase of adsorption capability and cooperativity, as well as the change of adsorption mechanism were detected in the adsorption of ofloxacin enantiomers on polynucleotides upon Cu(II)-coordination. This study not only discloses the effect of the chiral drug on the structural transition of long double-stranded DNA, but provides fundamental data to develop a novel enantioseparation method based on natural polynucleotides.

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Enantioselective binding of S- and R-ofloxacin to various synthetic polynucleotides

Cited by 25 publications

References 13 publications

Interaction Studies of an Anticancer Alkaloid, (+)-(13aS)-Deoxytylophorinine, with Calf Thymus DNA and Four Repeated Double-Helical DNAs

Interaction Studies of an Anticancer Alkaloid, (+)-(13aS)-Deoxytylophorinine, with Calf Thymus DNA and Four Repeated Double-Helical DNAs

Immuno-strip biosensor system to detect enrofloxacin residues

Intrinsic Enantioselectivity of Natural Polynucleotides Modulated by Copper Ions

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