Investigation of H-Bonding and pH on the Fluorescence Spectral Behavior of Valsartan.

IF 2.6 4区 化学 Q2 BIOCHEMICAL RESEARCH METHODS
Fakhri O Yousef, Raed Ghanem, Omar K Almashaqbeh, Ihsan A Shehadi
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引用次数: 0

Abstract

The photophysical properties of valsartan (VAL), a potent phenyl tetrazole derivative sartan, were investigated. Valsartan has absorption bands at 230 nm and 255 nm and a fluorescence band at about [Formula: see text] = 346 nm in butanol which is red shifted depending on the H-bonding capability of the solvent. The role of H-bonding in the excited state was approved through the linear correlation of the emission energy of VAL with Camlet-Taft acidity and basicity parameters, α and β, of polar protic solvents. The position and intensity of fluorescence emission bands of VAL are found to be pH dependent, shifting from 425 nm at pH 2 to 375 nm at pH 4 with enhancement of intermolecular H-bonding and fluorescence intensity depletion beyond pH 5 with formation of tetrazole anion. The results were supported by time-resolved fluorescence measurements which indicated the presence of different species with different lifetimes in the excited state depending on solution pH value. Computational results based on time dependent density functional methods (TDDFT) show that the tetrazole moiety is involved in the [Formula: see text] absorption transitions, while natural bond analysis (NBO) shows that VAL adopts a dimer conformation in water because of effective intermolecular H-bonding.

研究 H 键和 pH 对缬沙坦荧光光谱行为的影响
研究了缬沙坦(VAL)的光物理特性,缬沙坦是一种强效苯基四唑衍生物沙坦。在丁醇中,缬沙坦在 230 nm 和 255 nm 处有吸收带,在约 [式:见正文] = 346 nm 处有荧光带,该荧光带根据溶剂的 H 键能力发生红移。通过 VAL 的发射能量与极性质子溶剂的 Camlet-Taft 酸度和碱度参数 α 和 β 的线性相关关系,可以确定 H 键在激发态中的作用。研究发现,VAL 的荧光发射带的位置和强度与 pH 值有关,随着分子间 H 键的增强,荧光发射带从 pH 值为 2 时的 425 nm 波长移动到 pH 值为 4 时的 375 nm 波长,而当 pH 值超过 5 时,随着四氮唑阴离子的形成,荧光强度减弱。时间分辨荧光测量结果表明,根据溶液 pH 值的不同,激发态中存在不同物种,其寿命也不同。基于时间相关密度泛函法(TDDFT)的计算结果表明,四氮唑分子参与了[式中:见正文]的吸收转变,而自然键分析(NBO)则表明,由于分子间存在有效的氢键,VAL 在水中呈二聚体构象。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Journal of Fluorescence
Journal of Fluorescence 化学-分析化学
CiteScore
4.60
自引率
7.40%
发文量
203
审稿时长
5.4 months
期刊介绍: Journal of Fluorescence is an international forum for the publication of peer-reviewed original articles that advance the practice of this established spectroscopic technique. Topics covered include advances in theory/and or data analysis, studies of the photophysics of aromatic molecules, solvent, and environmental effects, development of stationary or time-resolved measurements, advances in fluorescence microscopy, imaging, photobleaching/recovery measurements, and/or phosphorescence for studies of cell biology, chemical biology and the advanced uses of fluorescence in flow cytometry/analysis, immunology, high throughput screening/drug discovery, DNA sequencing/arrays, genomics and proteomics. Typical applications might include studies of macromolecular dynamics and conformation, intracellular chemistry, and gene expression. The journal also publishes papers that describe the synthesis and characterization of new fluorophores, particularly those displaying unique sensitivities and/or optical properties. In addition to original articles, the Journal also publishes reviews, rapid communications, short communications, letters to the editor, topical news articles, and technical and design notes.
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