Synthesis of bridged and metallobridged bis(beta-cyclodextrin)s containing fluorescent oxamidobisbenzoyl linkers and their selective binding towards bile salts

Chemistry : a European Journal
Yu LiuYan-Li Zhao

Abstract

A series of beta-cyclodextrin (beta-CD) dimers containing fluorescent 2,2'-oxamidobisbenzoyl and 4,4'-oxamidobisbenzoyl linkers--that is, 6,6'-[2,2'-oxamidobis(benzoylamino)]ethyleneamino-6,6'-deoxy-bis(beta-CD) (2), 6,6'-[2,2'-oxamidobis(benzoylamino)]diethylenediamino-6,6'-deoxy-bis(beta-CD) (3), 6,6'-[4,4'-oxamidobis(benzoylamino)]ethyleneamino-6,6'-deoxy-bis(beta-CD) (4), and 6,6'-[4,4'-oxamidobis(benzoylamino)]diethylenediamino-6,6'-deoxy- bis(beta-CD) (5)--were synthesized from the corresponding oxamidobis(benzoic acid)s through treatment with mono[6-aminoethyleneamino-6-deoxy]-beta-CD or mono[6-diethylenetriamino-6-deoxy]-beta-CD. Further treatment of 2-5 with copper perchlorate gave their Cu(II) complexes 6-9 in satisfactory yields. The conformation and binding behavior of 2-9 towards two bile salt guests--sodium cholate (CA) and sodium deoxycholate (DCA)--was comprehensively investigated by circular dichroism, 2D NMR spectroscopy, and fluorescence spectroscopy in Tris-HCl buffer solution (pH 7.2) at 25 degrees C. Thanks to the cooperative host-linker-guest binding mode, the stoichiometric 1:1 complexes formed by bis(beta-CD)s 2-5 with bile salts gave high stability constants (KS values) of up to 10(3)-10(4) M(-1). Sign...Continue Reading

References

Dec 29, 2000·Chemistry : a European Journal·M R de JongD N Reinhoudt
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Citations

Jul 27, 2007·Chemistry : a European Journal·Olivia BistriMatthieu Sollogoub
Aug 20, 2009·Chemical Society Reviews·Francesco BelliaGraziella Vecchio
Jul 29, 2009·Chemistry : a European Journal·Juan M Casas-SolvasAntonio Vargas-Berenguel
Jun 4, 2010·Physical Chemistry Chemical Physics : PCCP·Hu XuDennis K P Ng
Jan 30, 2010·Chemical Society Reviews·Yong Chen, Yu Liu
Nov 30, 2020·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Wen-Jing ShiJin-Wu Yan
Jun 28, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Juan M Casas-SolvasAntonio Vargas-Berenguel

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