Roseophilin-inspired derivatives as transmembrane anion carriers

IF 2.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Supramolecular Chemistry Pub Date : 2021-09-02 DOI:10.1080/10610278.2022.2099277

Sandra Díaz-Cabrera, Israel Carreira-Barral, M. García-Valverde, R. Quesada

引用次数: 0

Abstract

ABSTRACT Roseophilin is an alkaloid structurally related to prodiginines . The intriguing pharmacological properties of these derivatives have prompted us to prepare synthetic compounds 1–3 inspired by their structure and to explore their transmembrane anion transport activity. The methoxyfuran heterocycle impacts the anionophoric activity of the compounds as a result of the reduced hydrogen-bonding ability and electrostatic repulsions between the oxygen in the furan ring and the anions. The position of the furan was also found to be crucial for determining their anion transport activity. Overall, replacement of the characteristic methoxypyrrole moiety of prodiginines and tambjamines by the methoxyfuran found in roseophilin is detrimental to their ability as anion carriers, suggesting that the biological activity of roseophilin is likely not related to their potential activity as anion carriers. Compound 2, bearing a furan ring attached to a dipyrromethene moiety, was found to be the most active anion carrier. GRAPHICAL ABSTRACT

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玫瑰红素衍生物作为跨膜阴离子载体

亲玫瑰碱是一种与子碱结构相似的生物碱。这些衍生物有趣的药理特性促使我们根据它们的结构制备合成化合物1-3，并探索它们的跨膜阴离子转运活性。甲氧基呋喃杂环由于降低了呋喃环上氧与阴离子之间的氢键能力和静电斥力而影响了化合物的阴离子活性。呋喃的位置也被发现对确定它们的阴离子运输活性至关重要。总的来说，在亲玫瑰素中发现的甲氧呋喃取代了特有的甲基吡咯部分，这不利于它们作为阴离子载体的能力，这表明亲玫瑰素的生物活性可能与它们作为阴离子载体的潜在活性无关。化合物2是最活跃的阴离子载体，其呋喃环与二吡咯烷基团相连。图形抽象

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来源期刊

Supramolecular Chemistry 化学-化学综合

CiteScore

3.60

自引率

3.00%

发文量

审稿时长

2.7 months

期刊介绍： Supramolecular Chemistry welcomes manuscripts from the fields and sub-disciplines related to supramolecular chemistry and non-covalent interactions. From host-guest chemistry, self-assembly and systems chemistry, through materials chemistry and biochemical systems, we interpret supramolecular chemistry in the broadest possible sense. Interdisciplinary manuscripts are particularly encouraged. Manuscript types include: high priority communications; full papers; reviews, and; Methods papers, techniques tutorials highlighting procedures and technologies that are important to the field. We aim to publish papers in a timely fashion and as soon as a paper has been accepted and typeset it will be published in electronic form on the Latest articles section of the website. The two most important review criteria are that the paper presents high-quality work that fits generally into the broad spectrum of activities in the supramolecular chemistry field. Under normal circumstances, Supramolecular Chemistry does not consider manuscripts that would be more suitable in a highly specialized journal. This includes, but is not limited to, those based mostly or exclusively on topics such as solid state/X-ray structures, computational chemistry, or electrochemistry. . The two most important review criteria are that the paper presents high-quality work that fits generally into the broad spectrum of activities in the supramolecular chemistry field.