A Selective G-Quadruplex DNA-Stabilizing Ligand Based on a Cyclic Naphthalene Diimide Derivative

Islam, Md. Monirul; Fujii, Satoshi; Sato, Shinobu; Okauchi, Tatsuo; Takenaka, Shigeori

doi:10.3390/molecules200610963

Cited by 36 publications

(36 citation statements)

References 44 publications

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“…Lysine and arginine were selected as the amino acid side chains owing to their structure and complementary charge to the G‐quadruplex backbone . The length of the side chain plays a key role in tethering the G‐quadruplex DNA binding ligands; a good correlation between shorter linker chains and their affinity for G‐quadruplex DNAs over duplex DNA has been reported . Additionally, the attachment of cationic charges on the peripheral substituents increase the aqueous solubility and is likely to influence the binding selectivity.…”

Section: Resultsmentioning

confidence: 99%

Amino‐Acid‐Derived Naphthalenediimides as Versatile G‐Quadruplex Binders

Răsădean

Sheng

Dash

et al. 2017

Chemistry A European J

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The design and synthesis of water soluble, amino-acid-functionalised naphthalenediimides (NDIs) as potential ligands of native G-quadruplexes is reported. The NDIs were tested on a panel of oncogene promoters, on the human telomeric sequence h-telo, and on double-stranded DNA. Out of the ligands tested, NDI 3 (N -Boc-l-lysine NDI) exhibited a highly discriminating nature by only stabilising the oncogene promoter c-kit2, which is up-regulated up to 80 % in ovarian, gastrointestinal, and breast malignancies.

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Section: Resultsmentioning

confidence: 99%

Amino‐Acid‐Derived Naphthalenediimides as Versatile G‐Quadruplex Binders

Răsădean

Sheng

Dash

et al. 2017

Chemistry A European J

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“…4d,e,f). In the absence of Piperine, the melting temperature (T m ) of Pu24T, tel22 and ckit21 were 75.0 °C42, 60.0 °C43 and 66.6 °C44 respectively (see Supplementary Table S2). After addition of Piperine, it has been observed that T m of the Pu24T DNA increased to 78.0 °C and 79.0 °C at D/N = 1.0 and 2.0 respectively.…”

Section: Resultsmentioning

confidence: 99%

Evidences for Piperine inhibiting cancer by targeting human G-quadruplex DNA sequences

Tawani

Amanullah

Mishra

et al. 2016

Sci Rep

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Piperine, a naturally occurring alkaloid, is well known as anti-oxidant, anti-mutagenic, anti-tumor and anti-proliferative agent. Piperine exerts such pharmacological activities by binding or interacting with various cellular targets. Recently, the first report for Piperine interaction with duplex DNA has been published last year but its interaction with G-quadruplex structures has not been studied yet. Herein, we report for the first time the interaction of Piperine with various DNA G-quadruplex structures. Comprehensive biophysical techniques were employed to determine the basis of interaction for the complex formed between Piperine and G-quadruplex DNA sequences. Piperine showed specificity for G-quadruplex DNA over double stranded DNA, with highest affinity for G-quadruplex structure formed at c-myc promoter region. Further, in-vitro studies show that Piperine causes apoptosis-mediated cell death that further emphasizes the potential of this natural product, Piperine, as a promising candidate for targeting G-quadruplex structure and thus, acts as a potent anti-cancer agent.

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“…[10] It also has been proved that G-quadruplex structures formed in G-rich telomeric DNA can inhibitt elomerase activity. [27,28] Our group has been workingo nd esigning novel G4 ligands with improveds pecificity for recognizingG -quadruplex, [29][30][31] and previously we reported cyclic naphthalene diimidec oupling with cyclohexane( cNDI-ch),w hich exhibited as ignificantly highera ffinity( 260-fold) towards binding with G-quadruplex than double-stranded DNA. [14] In addition, some reports already suggested that the G-quadruplex structure in the telomeric sequence assembled like beads on as tring, [15,16] G4 ligands which can selectively target multiple G4 repeats might be promisingf or furthere nhanced specificity on inhibiting telomerase function, and are attractingmore attentionf rom Gquadruplex researchers.…”

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confidence: 99%

Cyclic Naphthalene Diimide Dimer with a Strengthened Ability to Stabilize Dimeric G‐Quadruplex

Takeuchi

Zou

Wakahara

et al. 2019

Chemistry A European J

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An ew type of dimeric cyclic naphthalene diimide derivatives (cNDI-dimers)c arrying varied linker length were designed and synthesized to recognize dimeric G-quadruplex structures.A ll of the cNDI-dimerse xhibited ah igh preference for recognizing G-quadruplex structures, and significantly enhanced the thermals tability of the dimeric G-quadruplex structure over the cNDI monomer by increasing the melting temperature by more than 23 8C, which indicated the strengthened ability of cNDI dimers for stabilizing dimeric G-quadruplex. cNDI dimers also showed as tronger abilityt oi nhibitt elomerase activity and stop telomereD NA elongationt han cNDI monomer,w hich showed an improved anticancer potentiality for further therapeutic application.Te lomerase was thought to be essential for the immortalization of human cells, for its function in restoring telomeric DNA sequences. [1] It has been reported that telomerase was up-regulated in 85 %o fh uman cancerc ells, [2,3] and itsm utant with complete-activity inhibition could lead to the death of tumor cells. [4] In addition, telomerasei sg enerally not expressed in most normalh uman cells. These critical features lead to the rapid development of telomerase-targeted cancer therapiesi n advanced clinicaltrials. [5][6][7] Over past two decades, the four-stranded G-quadruplex nucleic acid structure has been of great interest as ap otential therapeutict arget, [8,9] for the important roles it has played in regulating gene expression and even translation. [10] It also has been proved that G-quadruplex structures formed in G-rich telomeric DNA can inhibitt elomerase activity. [11][12][13] For this reason,i ti sc onsidered as ap romising therapeuticp ath to develop small molecules, working as G4 ligands, to selectively stabilizeh uman telomeric DNA with four-stranded G-quadru-plex structures, further enhancing the inhibition of telomerase activity and inducing cancer cell death. [14] In addition, some reports already suggested that the G-quadruplex structure in the telomeric sequence assembled like beads on as tring, [15,16] G4 ligands which can selectively target multiple G4 repeats might be promisingf or furthere nhanced specificity on inhibiting telomerase function, and are attractingmore attentionf rom Gquadruplex researchers. Over the past several years, some ligandd imers [17][18][19][20][21][22][23][24] and tetramers [25] have been reported with a stronga bility to recognize dimerico rm ultiple G-quadruplex structures,w hich is supportedb yt he fact that the G4 ligand multimer might be ag ood model for stabilizing G-quadruplex repeats.As one important G4 ligand, naphthalene diimide can recognize the G-quadruplex structure through p-p stacking, [26] and its binding affinity to G-quadruplexw as rarely affected even underi nv ivo mimic molecular crowding conditionsa nd may represent superior telomerasei nhibitors in cell nuclei. [27,28] Our group has been workingo nd esigning novel G4 ligands with improveds pecificity for recognizingG -quadruplex, [29][30][31] and previously we...

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A Selective G-Quadruplex DNA-Stabilizing Ligand Based on a Cyclic Naphthalene Diimide Derivative

Cited by 36 publications

References 44 publications

Amino‐Acid‐Derived Naphthalenediimides as Versatile G‐Quadruplex Binders

Amino‐Acid‐Derived Naphthalenediimides as Versatile G‐Quadruplex Binders

Evidences for Piperine inhibiting cancer by targeting human G-quadruplex DNA sequences

Cyclic Naphthalene Diimide Dimer with a Strengthened Ability to Stabilize Dimeric G‐Quadruplex

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