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AAAA–DDDD Quadruple H‑Bond-Assisted Ionic Interactions: Robust Bis(guanidinium)/Dicarboxylate Heteroduplexes in Water
journal contribution
posted on 2019-12-13, 13:03 authored by Yuren Sun, Jun Gu, Hongyu Wang, Jonathan L. Sessler, Pall Thordarson, Yue-Jian Lin, Hegui GongThe use of geminal di(guanidinium) and acridin-9(10H)-one-derived di(carboxylate) derivatives (1a–c and 2a–e,
respectively) allows stabilization of heterodimers characterized by
high binding affinities in water (maximum ΔG < −7 kcal mol–1, Ka > 105 M–1) as inferred from
UV–vis spectroscopic titrations and ITC measurements, therefore
rivaling or surpassing the interaction energy between the strongest
DNA or RNA triplet pairs. These duplexes are readily accessible and
are structurally modifiable, rendering them attractive as building
blocks for creating heteroduplex constructs. Incorporating poly(ethylene
glycol)-decorated benzyl groups into the dicarboxylate, allows formation
of hydrogels in the case of 1b–2c.
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binding affinitiesmodifiableAAAAheterodimerRNA triplet pairsaffinityRobustBisacridinpolymolduplexeITC measurementsdicarboxylateglycolgeminalInteractionformationheteroduplexspectroscopicUVkcalstabilizationbuilding blocksHeteroduplexeQuadrupleDNAone-derivedbenzylderivativeIncorporatingΔ Ghydrogelinteraction energytitration