Influence of DNA Structures on the Conversion of Sanguinarine Alkanolamine Form to Iminium Form

Maiti, Motilal; Das, Suman; Sen, Anjana; Das, Arunangshu; Kumar, Gopinatha Suresh; Nandi, R.

doi:10.1080/07391102.2002.10506864

Cited by 48 publications

(41 citation statements)

References 33 publications

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“…This phenomenon indicates that DNA or chromatin removes the Sgr molecules from the nanoparticle surface and intercalate them inside their cages, a necessary prerequisite for successful drug delivery inside the cell 31,[40][41] . Acting ctDNA and other DNA materials as a strong intercalator for Sgr drug molecules has been explained and well documented by Maiti et al [30][31] and this strong affinity of DNA towards Sgr acts as a driving force to undock drug molecules from AuNP surface to intercalate them in DNA helix for effective drug delivery into cellular components. Due to large dimension of Sgr induced gold nanoparticle networking, it might be difficult for the Sgr-AuNP complex as a whole to enter into the cell through membrane pore but the selective affinity of Sgr for DNA intercalation can put them into the nuclei for effective drug delivery.…”

Section: Resultsmentioning

confidence: 97%

Development of a Triplet–Triplet Absorption Ruler: DNA- and Chromatin-Mediated Drug Molecule Release from a Nanosurface

Chakraborty¹,

Sau²,

Кузнецов

et al. 2016

J. Phys. Chem. B

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Triplet-triplet (T-T) absorption spectroscopy has been used successfully as a molecular ruler to understand the actual release process of sanguinarine as a drug molecule from a gold nanoparticle surface in the presence of cell components, that is, DNA and chromatin. The obtained results have been verified by fluorescence and surface-enhanced Raman spectroscopy (SERS), and a plausible explanation has been put forward to describe the underestimation and overestimation of the percentage (%) of the release of drug molecules measured by fluorescence- and SERS-based techniques, respectively, over the highlighted T-T absorption spectroscopy. Because of the intrinsic nature of absorption, the reported T-T absorption spectroscopic assay overpowers fluorescence- and SERS-based assays, which are limited by the long-range interaction and nonlinear dependence of the concentration of analytes, respectively.

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Section: Resultsmentioning

confidence: 97%

Development of a Triplet–Triplet Absorption Ruler: DNA- and Chromatin-Mediated Drug Molecule Release from a Nanosurface

Chakraborty¹,

Sau²,

Кузнецов

et al. 2016

J. Phys. Chem. B

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“…10c and d), and CD studies. 167 The results indicated the formation of structure I from structure II by a shift of equilibrium that was explained as in Scheme 6.…”

Section: E Influence Of Dna Structures On the Conversion Of Sanguinamentioning

confidence: 93%

“…110 Further, it was observed 167 that in presence of high concentration of DNA, the alkanolamine form (Structure II) was transformed to iminium form (Structure I)-DNA intercalated complex as revealed from spectrophotometric ( Fig. 10a and b), spectrofluorimetric ( Fig.…”

Section: E Influence Of Dna Structures On the Conversion Of Sanguinamentioning

confidence: 95%

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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161

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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“…Structurally, sanguinarine can exist between charged iminium and neutral alkanolamine forms while ethidium has no pH dependent structural change in the pH range 3 to 12 [39]. Sanguinarine exhibits guanine-cytosine specificity in its DNA binding aspect where as ethidium has no such clear-cut base pair specificity.…”

Section: Introductionmentioning

confidence: 98%

Thermodynamic profiles of the DNA binding of benzophenanthridines sanguinarine and ethidium: A comparative study with sequence specific polynucleotides

Hossain

Kumar

2010

The Journal of Chemical Thermodynamics

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Influence of DNA Structures on the Conversion of Sanguinarine Alkanolamine Form to Iminium Form

Cited by 48 publications

References 33 publications

Development of a Triplet–Triplet Absorption Ruler: DNA- and Chromatin-Mediated Drug Molecule Release from a Nanosurface

Development of a Triplet–Triplet Absorption Ruler: DNA- and Chromatin-Mediated Drug Molecule Release from a Nanosurface

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

Thermodynamic profiles of the DNA binding of benzophenanthridines sanguinarine and ethidium: A comparative study with sequence specific polynucleotides

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