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Synthetic Tripodal Squaramido‐Based Receptors for the Complexation of Antineoplastic Folates in Water
Author(s) -
Quiñonero David,
López Kenia A.,
Deyà Pere M.,
Piña M. Nieves,
Morey Jeroni
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100855
Subject(s) - chemistry , isothermal titration calorimetry , hydrogen bond , non covalent interactions , nuclear magnetic resonance spectroscopy , carboxylate , proton nmr , molecular recognition , spectroscopy , fluorescence spectroscopy , ammonium , computational chemistry , stereochemistry , combinatorial chemistry , molecule , organic chemistry , fluorescence , physics , quantum mechanics
Three suitably oriented squaramido ammonium groups form the basis of the first abiotic receptor that employs the noncovalent ammonium–carboxylate electrostatic interaction and a hydrogen bond to achieve high‐affinity molecular recognition in water. These interacctions have been studied experimentally by isothermal calorimetry (ITC), NMR spectroscopy, and MS. Also, we have proposed a model for coordination from DFT calculations and NMR spectroscopy studies. Finally, a fluorimetric ensemble of the receptor with 5‐carboxyfluorescein was useful for the quantitative fluorimetric determination of folate and methotrexate in commercial samples using competition assays.