2015
DOI: 10.1016/j.bmcl.2015.06.055
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AzaHx, a novel fluorescent, DNA minor groove and G·C recognition element: Synthesis and DNA binding properties of a p-anisyl-4-aza-benzimidazole-pyrrole-imidazole (azaHx-PI) polyamide

Abstract: The design, synthesis, and DNA binding properties of azaHx-PI or p-anisyl-4-aza-benzimidazole-pyrrole-imidazole (5) are described. AzaHx, 2-(p-anisyl)-4-aza-benzimidazole-5-carboxamide, is a novel, fluorescent DNA recognition element, derived from Hoechst 33258 to recognize G·C base pairs. Supported by theoretical data, the results from DNase I footprinting, CD, ΔT(M), and SPR studies provided evidence that an azaHx/IP pairing, formed from antiparallel stacking of two azaHx-PI molecules in a side-by-side manne… Show more

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Cited by 13 publications
(11 citation statements)
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“…[15,34,37,39] Pyridine-based hydrogen-bond-acceptor units (such as DB2120, Figure 1A), [30,34] and azabenzimidazole (azaBI) hydrogen-bond acceptors (DB2277, Figure 1A), [31,40] have recently been designedt or ecognize G·Cb pa nd complement the polyamidei midazole group. [4] Dervan's group and others have expanded the five-memberh ydrocycle used in polyamide. The amide-hydrocycle unit hasa lso been replaced with BI or azaBI to recognize A·TorG ·Cb ps.…”
Section: Compounds:design Conceptsmentioning
confidence: 99%
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“…[15,34,37,39] Pyridine-based hydrogen-bond-acceptor units (such as DB2120, Figure 1A), [30,34] and azabenzimidazole (azaBI) hydrogen-bond acceptors (DB2277, Figure 1A), [31,40] have recently been designedt or ecognize G·Cb pa nd complement the polyamidei midazole group. [4] Dervan's group and others have expanded the five-memberh ydrocycle used in polyamide. The amide-hydrocycle unit hasa lso been replaced with BI or azaBI to recognize A·TorG ·Cb ps.…”
Section: Compounds:design Conceptsmentioning
confidence: 99%
“…The amide-hydrocycle unit hasa lso been replaced with BI or azaBI to recognize A·TorG ·Cb ps. [4,[41][42][43][44] Our understanding of G·Cb pr ecognition by small molecule, minorgroove binders remains very limited, however,a nd additional molecular structures are needed to not only expand the use of the DNA as ac ellular drug receptor but also the compound uptake potentialind ifferent organismsand cell types.…”
Section: Compounds:design Conceptsmentioning
confidence: 99%
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“…Recently, Hartley et al designed and synthesized a hybrid fluorescent HP polyamide conjugate 22 ( Fig. 6 ) by attaching the A·T recognizing fluorophore, p -anisylbenzimidazolecarboxamido (Hx) in order to target the inverted CCAAT box 2 (ICB2) of the topoisomerase IIα (topo IIα) promoter and to monitor the cellar uptake of the conjugate [ 80 81 ]. Gratifyingly, conjugate 22 targets the 5'-TACGAT-3' sequence of the 5' flank of ICB2 with high affinity and sequence specificity, thereby disrupting the NF-Y-ICB2 interaction.…”
Section: Reviewmentioning
confidence: 99%
“…Imidazopyridines have the ability to influence many cellular pathways necessary for the proper functioning of cancerous cells. The inhibited proteins include, inter alia, matrix metalloproteinase-2, RNA-dependent RNA polymerase, hepatocyte growth factor receptor (c-MET), serine/threonine-protein kinase or cell division cycle 25 phosphatases [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ].…”
Section: Biological Properties Of Imidazo[45- B mentioning
confidence: 99%