LAPEN, Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo (USP), Av. Prof. Lineu Prestes, 580-Bloco 13 sup., Cidade Universitária, São Paulo, SP, 05508-900, Brazil,
Mol Divers. 2013 Nov;17(4):711-20. doi: 10.1007/s11030-013-9467-5. Epub 2013 Aug 29.
Chagas disease and leishmaniasis are neglected tropical diseases, considered as a serious public health. Also, the drugs available for their treatment are toxic and exhibit questionable efficacy. Consequently, the discovery and development of new drug candidates are currently necessary. Dendrimers are highly branched molecules with extremely controlled structure. Those molecular systems display several biological applications (i.e., drug carriers), especially when the focus is prodrug design. Herein, a second generation of dendrimer prodrugs was planned to obtain potentially antichagasic and leishmanicide delivery systems. These dendrimers were composed by myo-inositol (core), L-malic acid (spacer), and three bioactive agents [hydroxymethylnitrofurazone (NFOH), quercetin, 3-hydroxyflavone]. The major aim of this study was to investigate the molecular properties (thermodynamics, steric, steric/electronic, electronic, and hydrophobic) to further describe intersamples relationships through either similarity indices or linear combinations of the original variables. Then, an exploratory data analysis, which comprises hierarchical cluster analysis (HCA) and principal components analysis (PCA), was carried out. Complementary findings were observed for PCA and HCA. Steric, intrinsic/steric, steric/electronic, steric/hydrophobic, hydrophobic, and electronic properties influenced the discrimination process. In addition, these molecular properties can also contribute to enzymatic hydrolysis mechanism elucidation, which depends upon the approximation and a subsequent nucleophilic attack to release the drug from the dendrimer prodrugs.
恰加斯病和利什曼病是被忽视的热带病,被认为是严重的公共卫生问题。此外,用于治疗这些疾病的药物具有毒性,疗效也存在疑问。因此,目前有必要发现和开发新的药物候选物。树突状聚合物是具有高度受控结构的高度分支分子。这些分子系统具有多种生物学应用(例如,药物载体),尤其是在关注前药设计时。在此,计划了第二代树突状聚合物前药,以获得潜在的抗恰加斯病和杀利什曼原虫药物输送系统。这些树突状聚合物由肌醇(核心)、L-苹果酸(间隔物)和三种生物活性物质[羟甲基硝基呋喃酮(NFOH)、槲皮素、3-羟基黄酮]组成。本研究的主要目的是研究分子性质(热力学、空间、空间/电子、电子和疏水性),通过相似性指数或原始变量的线性组合进一步描述样本间的关系。然后,进行了探索性数据分析,包括层次聚类分析(HCA)和主成分分析(PCA)。PCA 和 HCA 观察到互补的结果。空间、内在/空间、空间/电子、空间/疏水性、疏水性和电子性质影响了区分过程。此外,这些分子性质还可以有助于阐明酶促水解机制,这取决于对前药的近似和随后的亲核攻击,以将药物从树突状聚合物前药中释放出来。