Molecular recognition of DNA by small molecules: AT base pair specific intercalative binding of cytotoxic plant alkaloid palmatine

Bhadra, Kakali; Maiti, Motilal; Kumar, Gopinatha Suresh

doi:10.1016/j.bbagen.2007.03.001

Cited by 127 publications

(107 citation statements)

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“…UV-Spectroscopic analysis of palmatine -B-DNA complexation showed a very prominent bathochromic and hypochromic effect like berberine, with a K a value of 1.3 Â 10 4 m À 1 and site size of 7.9 base pairs (figure not shown). Like berberine, palmatine also has a very weak fluorescence, and binding to the nucleic acids enhanced this intrinsic fluorescence several folds [51]. With the corresponding B form, palmatine showed a non-cooperative binding with a K f value of 2.10 Â (Fig.…”

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Interaction of Isoquinoline Alkaloids with Polymorphic DNA Structures

Bhadra

Maiti

Kumar

2009

Chemistry & Biodiversity

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The interaction of berberine, palmatine, and coralyne with the B, Z, and H(L) form of poly[d(G-C)] was studied. Berberine and palmatine showed moderate binding to the B form, while coralyne showed higher binding, as revealed from spectroscopic and thermodynamic data. Berberine and coralyne binding to the B form was exothermic and enthalpy-driven, while palmatine showed exothermic binding which was favored by both negative enthalpy and negative entropy changes. Berberine and palmatine neither bind nor converted the Z-form structure to B form. Coralyne, on the other hand, exhibited a strong binding affinity to Z DNA structure that was enthalpy-driven. Berberine binding to the H(L) form was cooperative, exothermic, and favored by both negative enthalpy and negative entropy changes with the formation of an induced CD band. Palmatine showed weak binding, while coralyne showed a strong binding with the H(L) form. The structural differences in the isoquinoline alkaloids appear to influence the affinity and mode of interactions with these polymorphic DNA structures.

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Interaction of Isoquinoline Alkaloids with Polymorphic DNA Structures

Bhadra

Maiti

Kumar

2009

Chemistry & Biodiversity

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“…31 Similar cooperativitity in binding of analogous complexes with DNA have also been observed. 22,32 When substituting these data (ν and…”

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Interaction Studies of a Novel, Water-Soluble and Anti-Cancer Palladim(II) Complex with Calf Thymus DNA

Mansouri‐Torshizi

Saeidifar²,

Divsalar³

et al. 2010

Bulletin of the Korean Chemical Society

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We report the preparation and characterization of a new and water soluble complex of palladium(II) with 1,10-phenanthroline and butyldithiocarbamate ligands. This compound has been studied through spectroscopic techniques, 1 H NMR, IR, electronic spectra and elemental analysis and conductivity measurements. The complex shows 50% cytotoxic concentration (Ic50) value against chronic myelogenous leukemia cell line, K562, much lower than that of cisplatin. Thus the mode of binding of this complex to calf thymus DNA have been extensively investigated by isothermal titration UV-visible spectrophotometry, fluorescence, gel filteration and other methods. UV-visible studies show that the complex exhibits cooperative binding with DNA and remarkably denatures the DNA at extremely low concentration (~13 µM). Fluorescence studies indicate that the complex intercalate into DNA. Gel filtration studies suggest that the binding of Pd(II) complex with DNA is strong enough that it does not readily break. In these interaction studies, several thermodynamic and binding parameters are also determined which may reflect the mechanism of action of this type of compound with DNA.

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“…(4). Generally, cooperative binding is mediated by allosteric effects [21,24,25,[29][30][31]. Scatchard plot from the interaction of harmaline with CT DNA indicates [inset of Figure 4a] intrinsic binding affinity, K i ω (product of cooperative binding affinity and the cooperative factor) in the order of 5.60 × 10 5 /M with a stoichiometry of 4 nucleotide phosphates.…”

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confidence: 99%

“…, fluorescence quenching study was performed as described previously [28,29]. The data were plotted as Stern-Volmer plots of Io/I versus [Fe (CN)6] 4_ .…”

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Therapeutic potential of harmaline, a novel alkaloid, against cervical cancer cells in vitro: Apoptotic induction and DNA interaction study

2018

J App Biol Biotech

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The study emphasizes the growth inhibitory effect of harmaline on HeLa (human cervical cancer) cell line and mode and mechanism of binding with CT DNA (calf thymus DNA). The results of cytotoxic study performed through MTT assay indicates that harmaline have concentration dependent growth inhibitory effect on HeLa cell line with GI 50 value of 28 µM. Furthermore, the alkaloid induced DNA damage and changes in mitochondrial membrane potential in the cell line. The alkaloid shows reactive oxygen species dependent cellular damage with significant arrest in G 2 /M population of the cell. Biophysical experiments further established the K i w value (product of cooperative binding affinity and the cooperative factor) of harmaline with CT DNA to be 5.60 × 10 5 M −1. Harmaline showed a progressive quenching of the fluorescence emission spectra. Circular dichroism study shows significant structural changes of DNAwith subsequent induction of optical activity in the bound achiral alkaloid molecule. The alkaloid stabilizes the DNA to 10°C. Intercalated state of harmaline inside DNA helix was shown by viscometric and ferrocyanide quenching. The results highlight the importance of alkaloid-DNA interaction for developing nucleic acid based therapeutic agents.

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Molecular recognition of DNA by small molecules: AT base pair specific intercalative binding of cytotoxic plant alkaloid palmatine

Cited by 127 publications

References 50 publications

Interaction of Isoquinoline Alkaloids with Polymorphic DNA Structures

Interaction of Isoquinoline Alkaloids with Polymorphic DNA Structures

Interaction Studies of a Novel, Water-Soluble and Anti-Cancer Palladim(II) Complex with Calf Thymus DNA

Therapeutic potential of harmaline, a novel alkaloid, against cervical cancer cells in vitro: Apoptotic induction and DNA interaction study

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