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首页> 外文期刊>Chemistry: A European journal >Synthesis of Bridged and Metallobridged Bis(beta-cyclodextrin)s Containing Fluorescent Oxamidobisbenzoyl Linkers and Their Selective Binding towards Bile Salts
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Synthesis of Bridged and Metallobridged Bis(beta-cyclodextrin)s Containing Fluorescent Oxamidobisbenzoyl Linkers and Their Selective Binding towards Bile Salts

机译：含荧光酰胺基双苯甲酰基接头的桥联和金属桥联双（β-环糊精）的合成及其对胆盐的选择性结合。

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A series of beta-cyclodextrin(beta-CD)dimers containing fluorescent 2,2'-oxamidobisbenzoyl and 4,4'-oxamido-bisbenzoyl linkers-that is,6,6'-[2,2'-oxamidobis(benzoylamino)]ethyleneamino-6,6'-deoxy-bis(P-CD)(2),6,6'-[2,2'-oxamidobis(benzoylamino)]diethylene-diamino-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 deoxy cholate(DC A)-was comprehensively investigated by circular dichroism,2D NMR spectroscopy,and fluorescence spectroscopy in Tris-HCl buffer solution(pH 7.2)at 25 deg C.Thanks to the cooperative host-linkerguest binding mode,the stoichiometric 1:1 complexes formed by bis(beta-CD)s 2-5 with bile salts gave high stability constants(K_S values)of up to 10~3-10~4M~(-1).Significantly,benefiting from the intramolecular 1:2 or 2:4 binding stoichiometry,the resulting complexes of metallobis(beta-CD)s 6-9 with bile salts gave much higher K_S values of up to 10~6-10~7M~(-2).The enhanced binding abilities of bis(beta-CD)s and metallobridged bis(beta-CD)s are discussed from the viewpoints of induced-fit interactions and multiple recognition between host and guest.
机译：一系列β-环糊精（β-CD）二聚体，含有荧光2,2'-氧酰胺基双苯甲酰基和4,4'-氧酰胺基-双苯甲酰基接头，即6,6'-[2,2'-氧酰胺基双（苯甲酰氨基）]亚乙基氨基-6,6'-脱氧双（P-CD）（2），6,6'-[2,2'-氧酰胺基双（苯甲酰氨基）]二亚乙基-二氨基-6,6'-脱氧双（β- CD）（3），6,6'-[4,4'-乙酰胺基双（苯甲酰氨基）]亚乙基氨基-6,6'-脱氧双（β-CD）（4）和6,6'-[4，通过用单[6-氨基亚乙基氨基-6-]处理从相应的乙酰胺基双（苯甲酸）s合成4'-氧酰胺基双（苯甲酰基氨基）-二亚乙基二氨基-6,6'-脱氧-双（β-CD）（5）-。脱氧]-β-CD或单[6-二亚乙基三氨基-6-脱氧]-β-CD。用高氯酸铜进一步处理2-5得到令人满意的产率的Cu〜（II）配合物6-9。在Tris-HCl缓冲溶液（pH 7.2）中，通过圆二色性，二维NMR和荧光光谱，全面研究了2-9对两个胆盐客人-胆酸钠（CA）和脱氧胆酸钠（DCA）的行为t 25℃。由于主体-客体的协同结合，双（β-CD）2-5与胆盐形成的化学计量比为1：1的络合物具有高达10〜3的高稳定常数（K_S值） -10〜4M〜（-1）。明显地，由于分子内1：2或2：4的化学计量比，金属叶（β-CD）s 6-9与胆盐形成的配合物给出了更高的K_S值到10〜6-10〜7M〜（-2）。从诱导-拟合相互作用和宿主之间的多重识别的角度讨论了bis（β-CD）和金属桥联的bis（β-CD）的增强结合能力。和客人。

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