Combined Crystallographic and Solution Molecular Dynamics Study of Allosteric Effects in Ester and Ketone p-tert-Butylcalix[4]arene Derivatives and Their Complexes with Acetonitrile, Cd(II), and Pb(II)

Alexandre S. de Araujo; Oscar E. Piro; Eduardo E. Castellano

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Combined Crystallographic and Solution Molecular Dynamics Study of Allosteric Effects in Ester and Ketone p-tert-Butylcalix[4]arene Derivatives and Their Complexes with Acetonitrile, Cd(II), and Pb(II)

机译：酯和酮对叔丁基杯[4]芳烃衍生物及其与乙腈，Cd（II）和Pb（II）的配合物的变构效应的组合晶体学和溶液分子动力学研究

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We describe here a procedure to bridge the gap in the field of calixarene physicochemistry between solid-state atomic-resolution structural information and the liquid-state low-resolution thermodynamics and spectroscopic data. We use MD simulations to study the kinetics and energetics involved in the complexation of lower rim calix[4]arene derivatives (L), containing bidentate ester (1) and ketone (2) pendant groups, with acetonitrile molecule (MeCN) and Cd~(2+) and Pb~(2+) ions (M~(2+)) in acetonitrile solution. On one hand, we found that the prior inclusion of MeCN into the calix to form a L(MeCN) adduct has only a weak effect in preorganizing the hydrophilic cavity toward metal ion binding. On the other hand, the strong ion—hydrophilic cavity interaction produces a wide open calix which enhances the binding of one MeCN molecule (allosteric effect) to stabilize the whole (M~(2+))L(MeCN) bifunctional complex. We reach two major conclusions: (i) the MD results for the (M~(2+))l(MeCN) binding are in close agreement with the "endo", fully encapsulated, metal complex found by X-ray diffraction and in vacuo MD calculations, and (ii) the MD structure for the more flexible 2 ligand, however, differs from the also endo solid-state molecule. In fact, it shows strong solvation effects at the calixarene lower bore by competing MeCN molecules that share the metal coordination sphere with the four C=O oxygens of an "exo" (M~(2+))2(MeCN) complex.

机译：我们在这里描述了一种程序，以弥合固态原子分辨率的结构信息与液态低分辨率的热力学和光谱数据之间的杯芳烃理化领域的差距。我们使用MD模拟研究了包含二齿酸酯（1）和酮（2）侧基的下缘杯[4]芳烃衍生物（L）与乙腈分子（MeCN）和Cd〜的络合的动力学和能量学。乙腈溶液中的（2+）和Pb〜（2+）离子（M〜（2+））。一方面，我们发现将MeCN预先加入到杯状玻璃中以形成L（MeCN）加合物，在使亲水性腔体朝着金属离子结合的方向进行预组织方面仅具有微弱的作用。另一方面，强的离子-亲水腔相互作用产生宽开口杯，其增强了一个MeCN分子的结合（变构作用），从而稳定了整个（M〜（2 +））L（MeCN）双功能复合物。我们得出两个主要结论：（i）（M〜（2 +））l（MeCN）结合的MD结果与通过X射线衍射发现的“内切”，完全包封的金属络合物和在真空MD计算，以及（ii）更具柔韧性的2个配体的MD结构，也不同于内部固态分子。实际上，它通过与“ exo”（M〜（2 +））2（MeCN）络合物的四个C = O氧共享金属配位球而竞争的MeCN分子在杯芳烃下孔显示出强大的溶剂化作用。

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《The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory》 |2008年第46期|共10页
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Alexandre S. de Araujo; Oscar E. Piro; Eduardo E. Castellano;
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1. Combined Crystallographic and Solution Molecular Dynamics Study of Allosteric Effects in Ester and Ketone p-tert-Butylcalix[4]arene Derivatives and Their Complexes with Acetonitrile, Cd(II), and Pb(II) [J] . Alexandre S. de Araujo, Oscar E. Piro, Eduardo E. Castellano The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2008,第46期

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机译：代谢型谷氨酸受体3神经保护a. Berent-spillson和J. W. Russell于2006年6月12日收到;修订稿于2006年10月3日收到; 2006年10月5日接受。美国马里兰州巴尔的摩市南格林街22号，马里兰大学医学院神经病学系James W. Russell的地址通信和重印申请。电子邮件：jruss@umich.edu使用的缩写：apDC，2R，4R-4-氨基吡咯烷-2,4-二羧酸酯（特异性代谢型谷氨酸受体3激动剂）; BsO，丁硫氨酸亚砜亚胺（GsH合成抑制剂）;半胱天冬酶，半胱氨酸需要的天冬氨酸蛋白酶; CysGly，半胱氨酰甘氨酸（GsH降解产物）; DapI，4'-6-二脒基-2-苯基吲哚; DCF，二氯二氢荧光素; DCFDa，5-（和6） - 氯甲基-2'，7'-二氯二氢荧光素二乙酸酯，乙酰酯; DHE，二氢乙锭; DRG，背根神经节; FCCp，羰基氰化物4-（三氟甲氧基）苯腙（电子传输解偶联剂）; GCp II / III，谷氨酸羧肽酶II / III;谷胱甘肽;谷胱甘肽; GsH-EE，谷胱甘肽乙酯; GsT，谷胱甘肽-s-转移酶; H 2 O 2，过氧化氢; HBss，Hank的平衡盐溶液; JC-1,5,5'，6,6'-四氯-1,1'，3,3'-四乙基苯并咪唑基酞菁碘化物; mCB，monochlorobimane; mGluR，代谢型谷氨酸受体; NaaG，N-乙酰基 - 天冬氨酰谷氨酸; pBs，磷酸盐缓冲盐水; pCD，程序性细胞死亡; Rh123，罗丹明123;活性氧，活性氧; δψμ，线粒体内膜电位。代谢型谷氨酸受体3通过增加细胞内谷胱甘肽浓度来保护神经元免受葡萄糖诱导的氧化损伤
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Combined Crystallographic and Solution Molecular Dynamics Study of Allosteric Effects in Ester and Ketone p-tert-Butylcalix[4]arene Derivatives and Their Complexes with Acetonitrile, Cd(II), and Pb(II)

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