Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440011, India.
J Mol Model. 2013 Aug;19(8):3385-96. doi: 10.1007/s00894-013-1856-2. Epub 2013 May 18.
Pindolol (PDL) is a potent and specific adrenoreceptor blocking agent. It is widely used in the treatment of hypertension, cardiac arrhythmia and angina pectoris. Molecularly imprinted polymers (MIPs) are synthetic receptors having potential applications in drug delivery systems and devices such as diagnostic sensors. In the present work, ab initio quantum mechanical simulations and computational screening were used to identify functional monomer having best interactions with PDL. A virtual library of 16 functional monomers was built and the possible minimum energy conformation of the monomers and PDL were calculated using Hartree-Fock (HF) method for the synthesis of PDL imprinted polymer. The interaction energy between functional monomer and the template were corrected by means of basis set superposition error (BSSE) in all pre-polymerization complexes. The hydrogen bonding between PDL and functional monomer was evaluated by changes in bond lengths before and after complex formation. The virtual template-monomer complex with highest interaction energy is more stable during the polymerization and leads to high selectivity and specificity toward the template. The interaction energy of PDL was found to be the highest with itaconic acid followed by 4-vinyl pyridine and least with acrylonitrile. Taking a spectroscopic viewpoint, results obtained from analysis of the harmonic infrared spectrum were examined. Red and blue shifts related to the stretching frequencies of either donors or acceptors of protons were identified and compared experimentally. Stoichiometric mole ratio of template to functional monomer was optimized and confirmed by UV visible spectra titrations. The theoretical results were correlated by evaluation of binding parameters of MIPs. The experimental binding results were in good agreement with theoretical computations.
平哚洛尔（PDL）是一种强效且特异的肾上腺素受体阻滞剂。它被广泛用于治疗高血压、心律失常和心绞痛。分子印迹聚合物（MIPs）是一种合成受体，具有在药物传递系统和诊断传感器等设备中的潜在应用。在本工作中，我们使用从头算量子力学模拟和计算筛选来确定与 PDL 具有最佳相互作用的功能单体。构建了一个包含 16 种功能单体的虚拟库，并使用 Hartree-Fock（HF）方法计算了单体和 PDL 的可能最低能量构象，以合成 PDL 印迹聚合物。在所有预聚合配合物中，通过基组叠加误差（BSSE）校正了功能单体与模板之间的相互作用能。通过比较形成配合物前后键长的变化，评估了 PDL 与功能单体之间的氢键。具有最高相互作用能的虚拟模板-单体配合物在聚合过程中更稳定，从而对模板具有更高的选择性和特异性。PDL 的相互作用能与衣康酸最高，其次是 4-乙烯基吡啶，与丙烯腈最低。从光谱学的角度来看，分析谐频红外光谱得到的结果进行了检验。确定并比较了与质子供体或受体伸缩频率有关的红移和蓝移，并进行了实验验证。通过紫外可见光谱滴定优化并确认了模板与功能单体的化学计量摩尔比。通过评估 MIPs 的结合参数对理论结果进行了关联。实验结合结果与理论计算吻合良好。
