Electro-optical fluorescence studies on the DNA binding of medically active drugs

Ridler, P. J.; Jennings, B. R.

doi:10.1088/0031-9155/28/6/002

Cited by 9 publications

(8 citation statements)

References 14 publications

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“…1, the emission of 5 μM berberine alone is rather weak; while the presence of the fully matched DNA (FM) slightly increases the fluorescence response with emissions peaked at 538 nm by exciting at either 360 or 465 nm, which is in agreement with previous reports on the interactions of berberine with DNA. [34][35][36][37][38][39][40][41][42][43][44][45] Furthermore, berberine's emission is independent on the FM sequence used here (Fig. S1, ESI †).…”

Section: Resultsmentioning

confidence: 99%

“…[31][32][33] Nucleic acids have been thought to be the biological targets of berberine in manifesting its anticancer activity. It is widely believed that berberine can bind with double-stranded DNA (ds-DNA), [34][35][36][37][38][39][40][41] triplex DNA, 42,43 G-quadruplex DNA, 44,45 and RNA. 46,47 Berberine can even link two DNA molecules together in an end-to-end fashion.…”

Section: Introductionmentioning

confidence: 99%

“…46,47 Berberine can even link two DNA molecules together in an end-to-end fashion. 48 Because berberine has a polycondensate system with partial unsaturation in ring B (Scheme 1), which renders its polycyclic system slightly buckled, the binding mode of berberine to DNA could be partially intercalative, 34,35 completely intercalative, 36 groove-associative, 37 or electrostatic 41 by a sequence-dependent A/T 34,37,39 or G/C 38 selectivity, or no remarkable sequence selectivity. 40 Herein, we find that berberine binding to the AP site is dependent on the bases opposite the AP site and can be used to differentiate pyrimidines from purines with a fluorescence light-up response much higher than that for the fully matched DNAs without the AP site.…”

Section: Introductionmentioning

confidence: 99%

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Simultaneous fluorescence light-up and selective multicolor nucleobase recognition based on sequence-dependent strong binding of berberine to DNA abasic site

Shao

et al. 2012

Org. Biomol. Chem.

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Label-free DNA nucleobase recognition by fluorescent small molecules has received much attention due to its simplicity in mutation identification and drug screening. However, sequence-dependent fluorescence light-up nucleobase recognition and multicolor emission with individual emission energy for individual nucleobases have been seldom realized. Herein, an abasic site (AP site) in a DNA duplex was employed as a binding field for berberine, one of isoquinoline alkaloids. Unlike weak binding of berberine to the fully matched DNAs without the AP site, strong binding of berberine to the AP site occurs and the berberine's fluorescence light-up behaviors are highly dependent on the target nucleobases opposite the AP site in which the targets thymine and cytosine produce dual emission bands, while the targets guanine and adenine only give a single emission band. Furthermore, more intense emissions are observed for the target pyrimidines than purines. The flanking bases of the AP site also produce some modifications of the berberine's emission behavior. The binding selectivity of berberine at the AP site is also confirmed by measurements of fluorescence resonance energy transfer, excited-state lifetime, DNA melting and fluorescence quenching by ferrocyanide and sodium chloride. It is expected that the target pyrimidines cause berberine to be stacked well within DNA base pairs near the AP site, which results in a strong resonance coupling of the electronic transitions to the particular vibration mode to produce the dual emissions. The fluorescent signal-on and emission energy-modulated sensing for nucleobases based on this fluorophore is substantially advantageous over the previously used fluorophores. We expect that this approach will be developed as a practical device for differentiating pyrimidines from purines by positioning an AP site toward a target that is available for readout by this alkaloid probe.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Simultaneous fluorescence light-up and selective multicolor nucleobase recognition based on sequence-dependent strong binding of berberine to DNA abasic site

Shao

et al. 2012

Org. Biomol. Chem.

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“…Subsequently, Maiti and coworkers studied the interaction of berberine with a variety of DNAs, from both natural and synthetic sources, in considerable detail with the help of different biophysical tools and proposed that the alkaloid binds more strongly to adenine‐thymine (AT) rich DNAs and by partial intercalative mode of binding 136–138. At the same time, with the use of electrooptical fluorescence studies, Ridler and Jennings showed that berberine intercalates to the DNA double helix 139. The partial intercalative model of binding of berberine was further supported from the subsequent 1 HNMR studies of Saran et al140 A strong affinity of berberine to DNA oligonucleotides was also reported by NMR and modeling studies of Mazzini et al141 although these authors favored a groove‐binding mode.…”

Section: Interaction Of Isoquinoline Alkaloids With Nucleic Acidsmentioning

confidence: 99%

Therapeutic potential of nucleic acid‐binding isoquinoline alkaloids: Binding aspects and implications for drug design

Bhadra

Kumar

2011

Medicinal Research Reviews

271

138

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Isoquinoline alkaloids represent a group of natural products with remarkable importance in the contemporary biomedical research and drug discovery programs. Several members of this group exhibit immense pharmacological and biological properties, including potential anticancer properties. Although the molecular targets of these alkaloids are not yet clearly delineated, extensive research in this area continues to build up new data that are clinically exploitable. The gross structural features of many of the members DNA interaction are more or less clear, but the mystery still remains on many aspects of their binding, including specificity and energetics. RNA-binding aspects of these alkaloids are being elucidated. More recent advancements in analytical instrumentation have enabled clearer elucidation and correlation of the structural and energetic aspects of the interaction. In this review, we report up-to-date details of the interaction of berberine, palmatine, and jatrorrhizine of the protoberberine group, sanguinarine from the benzophananthridine group, and several of their synthetic derivatives, such as coralyne, berberrubine, palmatrubine, and jatrorubin with nucleic acids have been reviewed. These studies, taken together up to now, have led to interesting knowledge on the mode, mechanism, specificity of binding, and correlation between structural aspects and energetics enabling a complete set of guidelines for design of new drugs. In contemporary research, several derivatives of these natural alkaloids are being prepared and investigated in several laboratories for ultimate discovery of new compounds that can be used as effective therapeutic agents.

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“…Similarly, drug molecules binding with macromolecular biological targets including blood proteins and DNA have been explored for several years [23][24][25][26]. However, even though cyclodextrins are known carriers that help in the sustained release of drugs, reports on the role of such carrier molecules in bringing the encapsulated molecules towards protein or DNA and their role in modulating the binding of drugs to the targets are scarce.…”

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confidence: 99%

The role of encapsulation by β-cyclodextrin in the interaction of raloxifene with macromolecular targets: a study by spectroscopy and molecular modeling

et al. 2014

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We report the binding of the drug raloxifene with Calf thymus DNA (ctDNA) and bovine serum albumin (BSA) in the presence and absence of β-cyclodextrin (β-CD) and explain the influence of β-cyclodextrin on the binding of the drug to macromolecules. UV-Vis absorption, fluorescence, proton nuclear magnetic resonance and two-dimensional rotating-frame nuclear overhauser effect spectroscopic techniques are used to study the stoichiometry and the binding strength of the complexes. Molecular modeling is used in combination with other techniques to propose the structure of the inclusion complex and the interaction with ctDNA. The Stern-Volmer quenching constants of the interaction of raloxifene with ctDNA in aqueous and β-CD solution are compared. The competition for binding of ctDNA with raloxifene and Methylene Blue is studied. The apparent binding constant and the number of binding sites for the binding of raloxifene with BSA in aqueous solution are significantly different from those in the presence of β-CD. The influence of β-CD on the binding of the small molecules with biological macromolecules is discussed. We infer that the binding strengths between raloxifene and macromolecules viz., ctDNA and BSA are influenced by the β-CD encapsulation. These results may suggest new ways to tune the drug binding to biomacromolecules by encapsulating specific moieties of drugs.

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Electro-optical fluorescence studies on the DNA binding of medically active drugs

Cited by 9 publications

References 14 publications

Simultaneous fluorescence light-up and selective multicolor nucleobase recognition based on sequence-dependent strong binding of berberine to DNA abasic site

Simultaneous fluorescence light-up and selective multicolor nucleobase recognition based on sequence-dependent strong binding of berberine to DNA abasic site

Therapeutic potential of nucleic acid‐binding isoquinoline alkaloids: Binding aspects and implications for drug design

The role of encapsulation by β-cyclodextrin in the interaction of raloxifene with macromolecular targets: a study by spectroscopy and molecular modeling

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