Topologically constrained bifunctional intercalators: DNA intercalation by a macrocyclic bisacridine

Zimmerman, Steven C.; Lamberson, Carol R.; Cory, Michael; Fairley, Terri A.

doi:10.1021/ja00199a047

Cited by 55 publications

(35 citation statements)

References 3 publications

(8 reference statements)

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“…A recent combined experimental and computational study provides support for that binding model in the major groove of the CUG RNA (24). By positioning the linking chain and triaminotriazine recognition units on opposite sides of the acridine unit, the bivalent complex likely requires a threading mechanism for binding (25). This design element was intentional with the goal of increasing the binding affinity through a higher residence time (26,27).…”

Section: Resultsmentioning

confidence: 99%

Single-molecule study of the CUG repeat–MBNL1 interaction and its inhibition by small molecules

Jahromi

Honda

Zimmerman

et al. 2013

Nucleic Acids Research

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Effective drug discovery and optimization can be accelerated by techniques capable of deconvoluting the complexities often present in targeted biological systems. We report a single-molecule approach to study the binding of an alternative splicing regulator, muscleblind-like 1 protein (MBNL1), to (CUG)n = 4,6 and the effect of small molecules on this interaction. Expanded CUG repeats (CUGexp) are the causative agent of myotonic dystrophy type 1 by sequestering MBNL1. MBNL1 is able to bind to the (CUG)n–inhibitor complex, indicating that the inhibition is not a straightforward competitive process. A simple ligand, highly selective for CUGexp, was used to design a new dimeric ligand that binds to (CUG)n almost 50-fold more tightly and is more effective in destabilizing MBNL1–(CUG)4. The single-molecule method and the analysis framework might be extended to the study of other biomolecular interactions.

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Section: Resultsmentioning

confidence: 99%

Single-molecule study of the CUG repeat–MBNL1 interaction and its inhibition by small molecules

Jahromi

Honda

Zimmerman

et al. 2013

Nucleic Acids Research

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“…Hence the chromophores of this diacridine violate neighbor exclusion. (23). They also found that both chromophores intercalate.…”

Section: Introductionmentioning

confidence: 94%

Polyelectrolyte Effects on 9-Aminoacridine-DNA Binding

Friedman

Shahin²,

Zuckerbraun

1991

Journal of Biomolecular Structure and Dynamics

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The 9-aminoacridine-DNA binding curve is analyzed in two ways: with polyelectrolyte effects neglected and with polyelectrolyte effects included. It is found that the analysis which includes polyelectrolyte effects is consistent with the violation of neighbor exclusion displayed by diacridine complexes as observed by Atwell et al. and by Zimmerman and coworkers. However the analysis which neglects polyelectrolyte effects is inconsistent with the diacridine results. This comparison supports the necessity of including polyelectrolyte effects in the analysis of drug-DNA binding curves.

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“…Quite a number of podands and macrocycles, as well as other derivatives, revealed applications as intercalating agents [65][66][67][68][69][70][71][72]. Macrocycles embedding these aromatic units also showed applications as sensors and chiral discriminators [73][74][75][76].…”

Section: Macrocycles With Phenothiazine Unitsmentioning

confidence: 99%

“…A bifunctional DNA intercalator, the bis(acridinium) cyclophane 83 with different bridges (peraza-tripropyleneoxide) and a chain generated by the reaction of -CH 2 Br substituents of the acridine moieties with N,N-bis(2-mercaptoethyl)succinamide, was obtained in a two steps strategy (Scheme 35) [72].…”

Section: Macrocycles With Phenothiazine Unitsmentioning

confidence: 99%

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Rednic

Hădade

Bogdan

et al. 2014

J Incl Phenom Macrocycl Chem

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Macrocycles emerged as an important class of useful compounds with multiple applications ranging from selective complexation of different anions, cations or neutral molecules to the development of new sensors, materials with improved properties and biologically active compounds. In this review we focus our discussion on the synthesis and structural analysis of macrocycles containing dibenzoheterocycles with sulphur and/or nitrogen atoms in the central six-membered ring (i.e. 10H-phenothiazine, 9,10-dihydroacridine or acridane, acridone, thianthrene, phenoxathiine, acridine, phenazine). We further highlight selected application of these compounds as host molecules, DNA intercalating agents or enzyme inhibitors.

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Topologically constrained bifunctional intercalators: DNA intercalation by a macrocyclic bisacridine

Cited by 55 publications

References 3 publications

Single-molecule study of the CUG repeat–MBNL1 interaction and its inhibition by small molecules

Single-molecule study of the CUG repeat–MBNL1 interaction and its inhibition by small molecules

Polyelectrolyte Effects on 9-Aminoacridine-DNA Binding

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

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