Synthesis and binding ability of bile acid-based receptors for recognition of flavin analogues

Association constants of 2,6-bis(alkylcarbonylamino)pyridines (alkyl = methyl or ethyl) and their perfluoroalkyl analogues with succin-and maleimide as well as with 2,2 0 -dipyridylamine (complementary DAD and ADA hydrogen bonding motifs are responsible for formation of the associates) have been determined by NMR titrations and quantum chemical calculations. Interactions of 2,6-bis (alkylcarbonylamino)pyridines with imides differ by character from these of perfluoroalkyl analogues. Such large difference was not observed for the 2,2 0 -dipyridylamine associates. Since fluorine atoms cause carbonylamino groups to be stronger hydrogen bond donors, perfluorinated species of this type were found to be more stable. Single crystal X-ray structures of 2,6-bis(trifluoromethylcarbonylamino)pyridine and 2,6-bis(pentafluoroethylcarbonylamino)pyridine have been also determined.

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“…6. It is noteworthy that K assoc obtained now are comparable to these for other triple hydrogen-bonded systems [44,[50][51][52].…”

Section: Nmrsupporting

confidence: 72%

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

et al. 2010

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“…Cholic acid‐based cyclophanes7h and oligomers10b are known to bind glycoside derivatives in nonpolar media due to the hydrophilic cavities in the case of cyclophanes and possible reverse micelle‐like conformations of the oligomers. Phenyl β‐ D ‐glucopyranoside has been used as a guest to study glycoside binding of cholic acid‐based oligomers10b, d by NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Tuning the Efficiency of Dendritic Nanocarriers using Conformational Constraints

Satyanarayana

Maitra

2011

Chemistry An Asian Journal

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A series of deoxycholic and cholic acid-derived oligomers were synthesized and their ability to extract hydrophilic dye molecules of different structure, size, and functional groups into nonpolar media was studied. The structure of the dye and "dendritic effect" in the extraction process was examined using absorption spectroscopy and dynamic light scattering (DLS). The efficiency of structurally preorganized oligomers in the aggregation process was evaluated by 1-anilinonaphthalene-8-sulfonic acid (ANS) fluorescence studies. The possible formation of globular structures for higher-generation molecules was investigated by molecular modeling studies and the results were correlated with the anomaly observed in the extraction process with this molecule. The ability of these molecules for selective extraction of specific dyes from blended colors is also reported.

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“…The group of Maitra prepared a cyclic molecule that can bind F − due to hydrogen bonding ( Figure 13) [82] . Similar cyclic molecules were prepared for recognition of flavin analogues and uracil derivatives [83,84] . The group of Davis prepared many cyclic molecules based on bile acids in the 1990s [85,86] , and more recently they converted the hydroxyl groups of cholic acid to ammonium groups to obtain cationic cyclic molecules with enhanced facial amphiphilicity (Figure 14) [87] .…”

Section: Cyclic Moleculesmentioning

confidence: 99%

Biomaterials made of bile acids

Zhang

Zhu

2009

Sci. China Ser. B-Chem.

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The use of natural compounds in the preparation of new materials can improve the biocompatibility of the materials and avoid any potential toxicity of the degradation products when used for biomedical applications. Bile acids are amphiphilic molecules biosynthesized in the liver. They are used to prepare various polymers and oligomers. These polymers made of bile acids are promising materials in both biomedical and pharmaceutical fields.

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Synthesis and binding ability of bile acid-based receptors for recognition of flavin analogues

Cited by 25 publications

References 43 publications

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

Tuning the Efficiency of Dendritic Nanocarriers using Conformational Constraints

Biomaterials made of bile acids

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