Interaction of sanguinarine iminium and alkanolamine form with calf thymus DNA

Sen, Anjana; Maiti, Motilal

doi:10.1016/0006-2952(94)90510-x

Cited by 73 publications

(39 citation statements)

References 23 publications

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“…The recoveries of sanguinarine and chelerythrine were 40-60% in both water and urine because these two compounds are quaternary ammonium alkaloids and were tightly absorbed onto the SPE absorbent. However, in the blood samples, the recoveries were 5-11% for sanguinarine and chelerythrine, beside the reason above-mentioned, which can be interpreted that the presence of quaternary nitrogen atom led to the high binding capacity of sanguinarine and chelerythrine to cellular proteins and DNA in the blood [28][29][30][31]. As a result, sanguinarine and chelerythrine could not be detected in the blood samples with the proposed method.…”

Section: Sample Pretreatment Procedurescontrasting

confidence: 64%

Simultaneous Determination of Toxic Alkaloids in Blood and Urine by HPLC–ESI–MS/MS

Zhang

Huang

et al. 2012

Chromatographia

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A sensitive and selective method for simultaneous determination of 29 toxic alkaloids in human blood and 31 in urine using high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry was developed and validated. The samples were diluted with 0.1 mol L -1 HCl, and the target alkaloids were purified by solid phase extraction. The separation of 31 alkaloids was carried out on a C18 column using a gradient mobile phase with 10 mmol L -1 ammonium formate in water with 0.1% formic acid and methanol at the rate of 0.25 mL min -1 . The triple-quadrupole mass spectrometer equipped with an electrospray source in the positive mode was set up in the dynamic multiple reactions monitoring mode (dynamic MRM) to detect the ion transitions of 31 alkaloids. The calibration curves were linear over a range of 0.5-400, 1-400, or 4-400 lg L -1 for target alkaloids in human blood and urine, and the correlation coefficients (r 2 ) was higher than 0.9943. The limit of determination and limit of quantification were 0.2-1 and 0.5-4 lg L -1 for blood and urine, respectively. The only exceptions were sanguinarine and chelerythrine in human blood. All the target alkaloids were stable under the test condition. In addition, the solvent effect and reconstituted solution were investigated. The method was validated and proved to be accurate and precise over the studied concentrations and suitable for poisoning diagnosis and forensic toxicology.

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Section: Sample Pretreatment Procedurescontrasting

confidence: 64%

Simultaneous Determination of Toxic Alkaloids in Blood and Urine by HPLC–ESI–MS/MS

Zhang

Huang

et al. 2012

Chromatographia

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“…Smekal et al (1984) investigated the interaction of sanguinarine (alkanolamine) with duplex DNA and suggested that the alkanolamine form formed a partially intercalated complex. This observation was contradicted by Sen and Maiti (1994) based on results obtained from extensive spectrophotometry, fluorescence polarization anisotropy, thermal melting, circular dichroism, and viscometric analysis. It was reported (Sen and Maiti 1994;Maiti na Not available a Data obtained from Maiti et al (1984) and Nandi and Maiti (1985) b K a is the binding constant c ∆Tm is the difference between the T m of the DNA in the presence of alkaloid and the T m of the free DNA d β is the slope of the equation …”

Section: Sanguinarine (Alkanolamine)-b-dna Interactioncontrasting

confidence: 61%

Biophysical aspects and biological implications of the interaction of benzophenanthridine alkaloids with DNA

Maiti

Kumar

2009

Biophys Rev

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Benzophenanthridine alkaloids represent a very interesting and significant group of natural products that exhibit a broad range of biological and pharmacological properties. Among this group of alkaloids, sanguinarine, nitidine, fagaronine, and chelerythrine have the potential to form molecular complexes with DNA structures and have attracted recent attention for their possible clinical and pharmacological utility. This review focuses on the interaction of these alkaloids with polymorphic DNA structures (B-form, Z-form, H-form, and triple helical form) reported by several research groups employing various physical techniques such as spectrophotometry, spectrofluorimetry, circular dichroism, NMR spectroscopy, thermal melting, viscometry as well as thermodynamic analysis by isothermal titration calorimetry and differential scanning calorimetry to elucidate the mode and mechanism of action at the molecular level to determine the structure-activity relationship. DNA binding properties of these alkaloids are interpreted in relation to their biological activity.

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“…Both sanguinarine (iminium) and sanguinarine (alkanolamine) were originally reported to form full and partially intercalated complexes to duplex DNA by Smekal et al 161 However, this observation was contradicted by Sen and Maiti 166 based on results from (i) the absorption and fluorescence spectra, (ii) circular dichroism, (iii) thermal melting, (iv) fluorescence polarization anisotropy, and (v) viscosity. It is pertinent to point out that sanguinarine (alkanolamine) is neutral and its structure has a partial saturation leading to non-planarity while sanguinarine (iminium) form is charged and has a planar aromatic ring system.…”

Section: Sanguinarine (Alkanolamine)-b-dna Interactionmentioning

confidence: 94%

“…It was proposed that the alkanloamine form is unable to bind to DNA due to its neutrality and structural non-planarity. 166 …”

Section: Sanguinarine (Alkanolamine)-b-dna Interactionmentioning

confidence: 97%

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

Maiti

Kumar

2006

Medicinal Research Reviews

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164

103

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Alkaloids occupy an important position in chemistry and pharmacology. Among the various alkaloids, berberine and coralyne of the protoberberine group, sanguinarine of the benzophenanthridine group, and aristololactam-beta-d-glucoside of the aristolochia group have potential to form molecular complexes with nucleic acid structures and have attracted recent attention for their prospective clinical and pharmacological utility. This review highlights (i) the physicochemical properties of these alkaloids under various environmental conditions, (ii) the structure and functional aspects of various forms of deoxyribonucleic acid (DNA) (B-form, Z-form, H(L)-form, protonated form, and triple helical form) and ribonucleic acid (RNA) (A-form, protonated form, and triple helical form), and (iii) the interaction of these alkaloids with various polymorphic DNA and RNA structures reported by several research groups employing various analytical techniques like absorbance, fluorescence, circular dichroism, and NMR spectroscopy; electrospray ionization mass spectrometry, thermal melting, viscosity, and DNase footprinting as well as molecular modeling and thermodynamic studies to provide detailed binding mechanism at the molecular level for structure-activity relationship. Nucleic acids binding properties of these alkaloids are interpreted in relation to their biological activity.

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Interaction of sanguinarine iminium and alkanolamine form with calf thymus DNA

Cited by 73 publications

References 23 publications

Simultaneous Determination of Toxic Alkaloids in Blood and Urine by HPLC–ESI–MS/MS

Simultaneous Determination of Toxic Alkaloids in Blood and Urine by HPLC–ESI–MS/MS

Biophysical aspects and biological implications of the interaction of benzophenanthridine alkaloids with DNA

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

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