Mode of binding of the cytotoxic alkaloid berberine with the double helix oligonucleotide d(AAGAATTCTT)2

Mazzini, Stefania; Bellucci, Maria Cristina; Mondelli, R.

doi:10.1016/s0968-0896(02)00466-2

Cited by 141 publications

(129 citation statements)

References 21 publications

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“…Although the exact mechanisms remain unclarified, the inhibitory effect ofberberine on NF-kappa B activity is likely to playa potential role. Berberine, one of the most studied compounds among the naturally occurring protoberberine alkaloids, has a long history of medicinal use in many countries (30). The studies of pharmacologic modulation of berberine may help us to understand more about the anti-inflammatory properties of its clinical treatment in many different diseases as long as the pathogenesis is related with the inflammatory events.…”

Section: Berberine Dose-dependently Inhibited the Adhesion Of Thp-imentioning

confidence: 99%

Berberine Reduces Leukocyte Adhesion to Lps-Stimulated Endothelial Cells and Vcam-1 Expression Both In Vivo and In Vitro

et al. 2012

Int J Immunopathol Pharmacol

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Leukocyte adhesion to endothelium plays a critical initiating role in inflammation. Berberine, an antiinflammatory natural compound, is known to attenuate lipopolysaccharide (LPS)-induced lung injury and improve survival of endotoxemic animals with mechanism not fully clarified. This study investigated the effects of berberine on the LPS-induced leukocyte-endothelial cell adhesion both in vivo and in vitro. We first established an animal model to observe the in vivo LPS-induced adhesion of leukocytes to the endothelium of venules in the lung tissue dose-dependently. Pretreatment of LPS-stimulated rats with berberine for 1 h reduced the leukocyte-endothelium adhesion and vascular cell adhesion molecule-l (VCAM-l) expression in lung. Pretreatment of LPS-stimulated vascular endothelial cells with berberine also dose-dependently decreased the number of adhered THP-l cells and VCAM-l expression at both RNA and protein levels. Berberine was further confirmed to inhibit the nuclear translocation and DNA binding activity of LPS-activated nuclear factor-kappa B (NF-kappa B). These data demonstrated an additional molecular mechanism for the profound anti-inflammatory effect of berberine.

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Section: Berberine Dose-dependently Inhibited the Adhesion Of Thp-imentioning

confidence: 99%

Berberine Reduces Leukocyte Adhesion to Lps-Stimulated Endothelial Cells and Vcam-1 Expression Both In Vivo and In Vitro

et al. 2012

Int J Immunopathol Pharmacol

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“…Computeraided modeling study on the berberine-DNA complex has suggested that berberine binds to DNA from its C 5 -C 6 -N + -C 8 side (Figure 1). 13 This was experimentally supported by our earlier study that introducing bulky groups at the 9-position leads to a dramatic decrease in the binding affinity.…”

Section: A711mentioning

confidence: 58%

Synthesis and DNA-binding Properties of Trehalose-tethered Monomeric and Dimeric Berberines

Yong-min¹,

Zhou²,

Chen³

et al. 2013

Bulletin of the Korean Chemical Society

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Trehalose-tethered monomeric and dimeric berberines were synthesized in 50% and 30% from the reaction of berberrubine with 6-tosyl-α,α'-trehalose and 6,6'-ditosyl-α,α'-trehalose, respectively, and fully characterized by MS (HR and ESI) and NMR ( 1 H, 13C, COSY and HSQC). Spectrophotometric and spectrofluorimetric titrations indicated that compared with berberine, trehalose-tethered monomeric berberine had comparable DNA-binding affinity toward calf-thymus DNA, whereas trehalose-spaced dimeric berberine exhibited higher DNA-binding affinity. The potential application of these conjugates is also briefly discussed.

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“…The observation of few specific intermolecular NOEs between the berberine and the oligonucleotide suggests that some binding preferences are expressed for certain base steps of the oligonucleotide under NMR conditions. 36 The quality of spectra of berberine-HP14 however precludes any comments on binding preferences for this protoberberine analog.…”

Section: Discussionmentioning

confidence: 99%

DNA Binding Mode of the Isoquinoline Alkaloid Berberine with the Deoxyoligonucleotide d(GCCGTCGTTTTACA)₂

Park

Kim

Sung

et al. 2004

Bulletin of the Korean Chemical Society

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The ability of protoberberine alkaloids, berberine and berberrubine, to act as topoisomerase II poisons is linked to the anti-cancer activity. Minor alterations in structure have a significant effect on their relative activity. Berberine, which has methoxy group at the 19-position, is significantly less potent than berberrubine. Several observations support non-specific binding to HP14 by the berberine: (i) nonspecific upfield changes in 1 H chemical shift for protons of the berberine; (ii) the broadening of imino protons of HP14 upon binding of the berberine; (iii) very small increases in duplex melting temperature in the presence of the berberine. Our results reveal that substitution of a hydroxyl group to a methoxy group on the 19-position, thereby converting the berberrubine to the berberine is associated with a non-specific DNA binding affinity and a reduced topoisomerase II poisoning. The presence of a bulky 19-methoxy substituent decreases intercalating properties of berberine and makes it inactive as topoisomerase II poison.

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Mode of binding of the cytotoxic alkaloid berberine with the double helix oligonucleotide d(AAGAATTCTT)2

Cited by 141 publications

References 21 publications

Berberine Reduces Leukocyte Adhesion to Lps-Stimulated Endothelial Cells and Vcam-1 Expression Both In Vivo and In Vitro

Berberine Reduces Leukocyte Adhesion to Lps-Stimulated Endothelial Cells and Vcam-1 Expression Both In Vivo and In Vitro

Synthesis and DNA-binding Properties of Trehalose-tethered Monomeric and Dimeric Berberines

DNA Binding Mode of the Isoquinoline Alkaloid Berberine with the Deoxyoligonucleotide d(GCCGTCGTTTTACA)₂

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Mode of binding of the cytotoxic alkaloid berberine with the double helix oligonucleotide d(AAGAATTCTT)2

Cited by 141 publications

References 21 publications

Berberine Reduces Leukocyte Adhesion to Lps-Stimulated Endothelial Cells and Vcam-1 Expression Both In Vivo and In Vitro

Berberine Reduces Leukocyte Adhesion to Lps-Stimulated Endothelial Cells and Vcam-1 Expression Both In Vivo and In Vitro

Synthesis and DNA-binding Properties of Trehalose-tethered Monomeric and Dimeric Berberines

DNA Binding Mode of the Isoquinoline Alkaloid Berberine with the Deoxyoligonucleotide d(GCCGTCGTTTTACA)2

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DNA Binding Mode of the Isoquinoline Alkaloid Berberine with the Deoxyoligonucleotide d(GCCGTCGTTTTACA)₂