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首页> 外文期刊>Biotechnic and Histochemistry >Alternative methods for estimating common descriptors for QSAR studies of dyes and fluorescent probes using molecular modeling software. 2. Correlations between log P and the hydrophilic/lipophilic index, and new methods for estimating degrees of amphiphilicity
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Alternative methods for estimating common descriptors for QSAR studies of dyes and fluorescent probes using molecular modeling software. 2. Correlations between log P and the hydrophilic/lipophilic index, and new methods for estimating degrees of amphiphilicity

机译：使用分子建模软件来估计染料和荧光探针的QSAR研究通用描述符的替代方法。 2. log P与亲水/亲脂指数之间的相关性，以及估计两亲性的新方法

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The log P descriptor, despite its usefulness, can be difficult to use, especially for researchers lacking skills in physical chemistry. Moreover this classic measure has been determined in numerous ways, which can result in inconsistant estimates of log P values, especially for relatively complex molecules such as fluorescent probes. Novel measures of hydrophilicity/ lipophilicity (the Hydrophilic/Lipophilic Index, HLI) and amphiphilicity (hydrophilic/lipophilic indices for the head group and tail, HLI T and HLI HG, respectively) therefore have been devised. We compare these descriptors with measures based on log P, the standard method for quantitative structure activity relationships (QSAR) studies. HLI can be determined using widely available molecular modeling software, coupled with simple arithmetic calculations. It is based on partial atomic charges and is intended to be a standalone measure of hydrophilicity/lipophilicity. Given the wide application of log P, however, we investigated the correlation between HLI and log P using a test set of 56 fluorescent probes of widely different physicochemical character. Overall correlation was poor; however, correlation of HLI and log P for probes of narrowly specified charge types, i.e., non-ionic compounds, anions, conjugated cations, or zwitterions, was excellent. Values for probes with additional nonconjugated quaternary cations, however, were less well correlated. The newly devised HLI can be divided into domain-specific descriptors, HLI T and HLI HG in amphiphilic probes. Determinations of amphiphilicity, made independently by the authors using their respective methods, showed excellent agreement. Quantifying amphiphilicity from partial log P values of the head group (head group hydrophilicity; HGH) and tail (amphiphilicity index; AI) has proved useful for undertanding fluorescent probe action. The same limitations of log P apply to HGH and AI, however. The novel descriptors, HLI T and HLI HG, offer analogous advantages to those seen with HLI over log P. The high correlation between log P and HLI, and the concordance between the two systems for assessing amphiphilicity, provide a powerful tool for QSAR studies. It is possible now to select a probe with missing fragments, and thus no log P, AI or HGH; and to estimate these important descriptors from parameters derived from HLI.
机译：log P描述符尽管有用，但可能难以使用，尤其是对于缺乏物理化学技能的研究人员而言。此外，已经以多种方式确定了这种经典方法，这可能导致log P值的估计不一致，尤其是对于相对复杂的分子（例如荧光探针）。因此，已设计出亲水/亲脂性（亲水/亲脂性指数，HLI）和两亲性（头组和尾部的亲水性/亲脂性指数，分别为HLI T和HLI HG）的新量度。我们将这些描述符与基于log P的量度进行比较，log P是定量结构活性关系（QSAR）研究的标准方法。可以使用广泛使用的分子建模软件以及简单的算术计算来确定HLI。它基于部分原子电荷，旨在作为亲水性/亲脂性的独立度量。鉴于log P的广泛应用，我们使用了一组理化性质差异很大的56个荧光探针的测试套件，研究了HLI和log P之间的相关性。总体相关性较差;但是，对于狭义指定电荷类型（即非离子化合物，阴离子，共轭阳离子或两性离子）的探针，HLI和log P的相关性极好。但是，具有其他非共轭季铵阳离子的探针的相关性较低。在两亲性探针中，新设计的HLI可以分为域特定的描述符HLI T和HLI HG。作者使用各自的方法独立进行的两亲性测定显示出极好的一致性。从头组的部分log P值（头组亲水性; HGH）和尾部的两部分log P值（两亲性指数; AI）来定量两亲性已被证明有助于理解荧光探针的作用。 log P的相同限制适用于HGH和AI。新颖的描述符HLI T和HLI HG与HLI相比具有优于log P的优点。logP和HLI之间的高度相关性以及两个用于评估两亲性的系统之间的一致性，为QSAR研究提供了强大的工具。现在可以选择缺少片段的探针，因此没有log P，AI或HGH。并根据HLI得出的参数估算这些重要的描述符。

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