Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 6, Pages 1732-1740Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob02084g
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Funding
- Ministerio de Economia y Competitividad
- FEDER
- Generalitat Valenciana [CTQ2009-14288-CO4-0, CSD2010-00065, PROMETEO 2011/008]
- Ministry of Science, Education and Sport of Croatia [098-0982914-2918, 098-1191344-2860]
- COST Action [CM1005]
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Bis-polyaza pyridinophane scorpiands bind nucleotides in aqueous medium with 10-100 micromolar affinity, predominantly by electrostatic interactions between nucleotide phosphates and protonated aliphatic amines and assisted by aromatic stacking interactions. The pyridine-scorpiand receptor showed rare selectivity toward CMP with respect to other nucleotides, whereby two orders of magnitude affinity difference between CMP and UMP was the most appealing. The phenanthroline-scorpiand receptor revealed at pH 5 strong selectivity toward AMP with respect to other NMPs, based on the protonation of adenine heterocyclic N1. The results stress that the efficient recognition of small biomolecules within scorpiand-like receptors relies mostly on the electrostatic and H-bonding interactions despite the competitive interactions in the bulk solvent, thus supporting further optimisation of this versatile artificial moiety.
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