Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

Wamberg, Michael Chr.; Hassan, Allam A.; Bond, Andrew D.; Pedersen, Erik B.

doi:10.1016/j.tet.2006.09.017

Cited by 21 publications

(20 citation statements)

References 53 publications

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“…This observation is consistent with data obtained previously for DNA/DNA duplexes (see Table 2 allows optimal base stacking within duplex structures (Wamberg et al, 2006). Efficient regulation of a specific gene expression or RNA manipulation may be achieved via a sequence-selective cleavage of RNA.…”

Section: Acyclic Analogs With Nucleobases and Their Analogs With Intesupporting

confidence: 92%

“…In subsequent studies those non-nucleoside analogs with higher affinity toward RNA were investigated (Wamberg et al, 2006). Derivatives of 6H-indolo-[2,3-b ]quino- (Shi et al, 2004) xaline were obtained (Fig.…”

Section: Acyclic Analogs With Nucleobases and Their Analogs With Intementioning

confidence: 99%

“…2). The influence of the length of linkers on the stability of DNA/DNA, DNA/RNA and DNA/LNA complexes was studied (Wamberg et al, 2006). The data shown in Table 2 indicate that analogs with one or two carbons in the alkyl chain (4-6) lower the stability of DNA duplexes.…”

Section: Acyclic Analogs With Nucleobases and Their Analogs With Intementioning

confidence: 99%

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Non-nucleosidic analogs of nucleic acids

Brzezinska¹,

Adrych-Rożek²,

Jahnz‐Wechmann³

et al. 2012

bta

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This paper presents several analogs of nucleic acids, including their structure and selected physico-chemical properties, reported recently as being obtained from non-nucleosidic units connected via phosphorodiester bonds. These analogs are built from units that instead of sugar residues carry different diol structures functionalized either with natural nucleobases or with other ring systems of an aromatic character. Some interesting nonnucleosidic oligonucleotide analogs and their applications are described. Unlocked (UNA) and glycerol nucleic acids (GNA) are also described.

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Section: Acyclic Analogs With Nucleobases and Their Analogs With Intesupporting

confidence: 92%

Section: Acyclic Analogs With Nucleobases and Their Analogs With Intementioning

confidence: 99%

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Non-nucleosidic analogs of nucleic acids

Brzezinska¹,

Adrych-Rożek²,

Jahnz‐Wechmann³

et al. 2012

bta

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“…Derivatives of this tetracyclic heteroaromatic system are important DNA interchelators [5 -8], some of which display antitumor activity [5 -7], while others are useful agents for the treatment of autoimmune disease [9] and multiple sclerosis [10]. Certain derivatives with basic appendages at the N(6)-position, such as 2 [8] (Fig. 1), exhibit potent antiviral activity [11 -14] against e. g., herpes simplex virus type 1 (HSV-1), cytomegalo virus (CMV) and vericella-zoster virus (VZV).…”

Section: Introductionmentioning

confidence: 99%

Heterocycles [c]-Fused onto Indoloquinoxaline. Synthesis of Novel Pyrano[2’,3’:4,5]indolo[2,3-b]quinoxalin-2-ones

Habashneh

El‐Abadelah

Abadleh

et al. 2012

Zeitschrift Für Naturforschung B

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“…Here we perform extensive spectroscopic studies to investigate the interaction between the novel indoloquinoxaline derivatives (4)(5)(6)(7)(8) and DNA by determining the binding constant, the binding geometry and the AT-specificity. The variation in the structure, such as in the linker length and its position, the permanent/non-permanent quaternary nitrogen salt and the introduction of new substituent groups on the indoloquinoxaline moiety, are shown to have an immediate significant influence on the interaction between the ligands and DNA.…”

Section: Introductionmentioning

confidence: 99%

Interactions of Antiviral Indolo[2,3-b]quinoxaline Derivatives with DNA

2008

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RECEIVED DATE (to be automatically inserted after your manuscript is accepted if required according to the journal that you are submitting your paper to) Abbreviations: 11,11, poly(dAdT)2, duplex of two alternating adenine-thymine polynucleotides; RA, rheumatoid arthritis; 2 SAR, structure activity relationship; SDS, sodium dodecyl sulphate; VZV, varicella-zoster virus; YO, oxazole yellow; YOYO, homodimeric derivative of oxazole yellow (YO).3 AbstractHere we present the synthesis of five novel indoloquinoxaline derivatives and investigate the DNA binding properties of these monomeric as well as dimeric compounds using absorption, fluorescence and linear dichroism. Several of the mono-and di-cationic derivatives presented have previously demonstrated an excellent antiviral effect that is higher than already acknowledged agents against human cytomegalovirus (CMV), herpes simplex virus type 1 (HSV-1) and varicella-zoster virus (VZV).We find that the DNA binding constants of the monomeric and dimeric derivatives are high (10 6 ) and very high (10 9 ), respectively. Results from the spectroscopic measurements show that the planar aromatic indoloquinoxaline moieties upon interaction with DNA intercalate between the nucleobases.Furthermore, we use poly(dA-dT) 2 and calf thymus DNA in a competitive binding experiment to show that all our derivatives have an AT-region preference. The findings are important in the understanding of the antiviral effect of these derivatives and give invaluable information for the future optimization of the DNA binding properties of this kind of drugs.4

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Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

Cited by 21 publications

References 53 publications

Non-nucleosidic analogs of nucleic acids

Non-nucleosidic analogs of nucleic acids

Heterocycles [c]-Fused onto Indoloquinoxaline. Synthesis of Novel Pyrano[2’,3’:4,5]indolo[2,3-b]quinoxalin-2-ones

Interactions of Antiviral Indolo[2,3-b]quinoxaline Derivatives with DNA

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