Targeting Loop Adenines in G‐Quadruplex by a Selective Oxirane

Doria, Filippo; Nadai, Matteo; Folini, Marco; Scalabrin, Matteo; Germani, Luca; Sattin, Giovanna; Mella, Mariella; Palumbo, Manlio; Zaffaroni, Nadia; Fabris, Daniele; Freccero, Mauro; Richter, Sara N.

doi:10.1002/chem.201203097

Cited by 79 publications

(58 citation statements)

References 45 publications

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“…In the last decade, a large number of studies have exploited the naphthalene diimide (NDI) moiety as a G4‐binding motif, taking advantage of its synthetic accessibility, optoelectronic, G4 binding, and sensing properties . Tri‐ and tetrasubstituted NDIs have been broadly explored NDIs due to their potency and duplex versus G4 selectivity, and have proven to be effective cores for multimodal reactive and photoreactive NDI conjugates, and even targeting human medullary thyroid cancer . Tetrasubstituted NDIs have shown bimodal fluorescence and photocytotoxicity, high affinity for hTel G4 DNA, antiproliferative potency in pancreatic cancer cells and inhibition of telomerase activity …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Binding Properties, and Differences in Cell Uptake of G‐Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates

Arévalo-Ruiz

Doria

Belmonte-Reche

et al. 2017

Chemistry A European J

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Registro de acceso restringido Este recurso no está disponible en acceso abierto por política de la editorial. No obstante, se puede acceder al texto completo desde la Universitat Jaume I o si el usuario cuenta con suscripción. Registre d'accés restringit Aquest recurs no està disponible en accés obert per política de l'editorial. No obstant això, es pot accedir al text complet des de la Universitat Jaume I o si l'usuari compta amb subscripció. Restricted access item This item isn't open access because of publisher's policy. The full--text version is only available from Jaume I University or if the user has a running suscription to the publisher's contents.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Binding Properties, and Differences in Cell Uptake of G‐Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates

Arévalo-Ruiz

Doria

Belmonte-Reche

et al. 2017

Chemistry A European J

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“…Chemical agents capable of inducing ICLs have been developed for biological applications, such as for DNA damage and repair studies, [1–5] as anticancer agents, [6] for nucleic acid detection, [7,8] for targeting telomeric G-quadruplex structures, [9,10] and for construction of DNA nanomaterials. [11] Over the past few decades, several research groups have developed novel chemical methods for inducing ICL formation, such as photoirradiation, oxidation, reduction, fluoride induction, and H 2 O 2 induction.…”

mentioning

confidence: 99%

Photoswitchable Formation of a DNA Interstrand Cross‐Link by a Coumarin‐Modified Nucleotide

et al. 2014

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A coumarin-modified pyrimidine nucleoside (1) has been synthesized using Cu(I)-catalyzed click reaction and incorporated into oligodeoxynucleotides (ODNs). Interstrand cross-links are produced upon irradiation of ODN containing 1 at 350 nm. Cross-linking occurs via [2+2] cycloaddition reaction with the opposing thymidine, 2′-deoxycytidine, or 2′-deoxyadenosine. A much higher reactivity was observed with dT than dC or dA. Irradiation of the dT-1 and dC-1 cross-linked products at 254 nm leads to a reversible ring-opening reaction, while such phenomenon was not observed with dA-1 adducts. The reversible reaction is ultrafast and complete within 50 s – 90 s. Consistent photoswitching behavior was observed over 6 cycles of irradiation at 350 nm and 254 nm. To the best of our knowledge, this is the first example of photoswitchable interstrand cross-linking formation induced by a modified pyrimidine nucleoside. Compound 1 is a novel tool for developing reversible DNA photoswitches which will lead to new applications in chemistry, biology, and nanotechnology.

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“…[22][23][24] The assay was performed using a guanine-rich DNA sequence that is accepted as a model of human telomeric G-quadruplex showing the peculiar TTAGGG repeat. 18 This sequence, from here on called "GQ" (5' -AGG GTT AGG GTT AGG GTT AGG GT -3', average mass 7270.774 Da), was incubated with the samples according to the conditions reported in the experimental part and in the Supplementary Material.…”

Section: Mass Spectrometry (Ms) Binding Assaymentioning

confidence: 99%

Constrained bisantrene derivatives as G-quadruplex binders

Ribaudo¹,

Scalabrin²,

Pavan³

et al. 2016

Arkivoc

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We here report the synthesis and evaluation of constrained derivatives of a bisantrene isomer known to bind DNA when structured in G-quadruplex. Enhanced high-resolution mass spectrometry was used to evaluate the binding efficiency and stoichiometry of the compounds towards G-quadruplex DNA using a duplex sequence for comparison. Fluorimetric DNA binding studies supported and confirmed these preliminary observations. One of the newly synthesized compounds showed a high tendency and specificity to bind the structured G-quadruplex DNA.

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Targeting Loop Adenines in G‐Quadruplex by a Selective Oxirane

Cited by 79 publications

References 45 publications

Synthesis, Binding Properties, and Differences in Cell Uptake of G‐Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates

Synthesis, Binding Properties, and Differences in Cell Uptake of G‐Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates

Photoswitchable Formation of a DNA Interstrand Cross‐Link by a Coumarin‐Modified Nucleotide

Constrained bisantrene derivatives as G-quadruplex binders

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