7-氯-4-(苯基苯丙氨酰)喹啉的结构-活性关系:对小鼠的新型抗痛觉和抗炎作用

IF 2.3 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY Chemistry & Biodiversity Pub Date : 2024-10-21 DOI:10.1002/cbdv.202301246
Vanessa Macedo, Ketlyn P da Motta, Carolina C Martins, Briana B Lemos, Allya Larroza, Roberto B Morais, Rodrigo K Steinhorst, Juliano A Roehrs, Diego Alves, Cristiane Luchese, Ethel Wilhelm
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引用次数: 0

摘要

7-氯-4-(苯基硒基)喹啉(4-PSQ)具有潜在的抗痛觉和抗炎活性。因此,在本研究中,我们研究了 4-PSQ 及其类似物 7-氯-4-[(4-氟苯基)硒基]喹啉(a)、7-氯-4-{[3-三氟甲基]苯基硒基}喹啉(b)、4-((3,5-双(三氟甲基)苯基)硒基)-7-氯喹啉(c)的结构-活性关系、7-氯-4-[(2,4,6-三甲基)硒基]喹啉酸 (d) 和 7-氯喹啉-4-硒酸 (e) 在小鼠急性炎症和化学、热和机械痛觉模型中的应用,以及通过硅学方法进行的研究。化合物 a(-F)、b(-CF3)、c(-Bis-CF3)、d(-CH3)、e(-OOH)和 4-PSQ 在化学和热痛觉模型中具有抗痛觉作用,只有化合物 d(-CH3)和 e(-OOH)在热板试验中未显示抗痛觉作用。此外,所有化合物都不会引起小鼠运动变化。化合物的硅学数据显示,只有化合物 c(Bis-CF3)的胃肠道吸收率较低,而化合物 c(Bis-CF3)和 e(-OOH)不具备穿透血脑屏障的能力,这表明化合物 e(-OOH)没有产生中枢性抗痛觉作用。此外,我们还发现这类化合物对 COX-2 的亲和力高于 COX-1。总之,我们的数据表明,插入取代基可以改变 4-PSQ 作为抗痛觉和抗炎剂的效率。
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Structure-Activity Relationship of 7-Chloro-4-(Phenylselanyl) Quinoline: Novel Antinociceptive and Anti-Inflammatory Effects in Mice.

The 7-chloro-4-(phenylselanyl)quinoline (4-PSQ) stands out for its potential antinociceptive and anti-inflammatory activities. Thus, in this study we investigated the structure-activity relationship of 4-PSQ and its analogues 7-chloro-4-[(4-fluorophenyl) selanyl]quinoline (a), 7-chloro-4-{[3-trifluoromethyl)phenyl] selanyl}quinoline (b), 4-((3,5-Bis(trifluoromethyl)phenyl)selanyl-7-chloroquinoline (c), 7-chloro-4-[(2,4,6-trimethyl)selanyl]quinolinic acid (d) and 7-chloroquinoline-4-selenium acid (e) in models of acute inflammation and chemical, thermal and mechanical nociception in mice, as well as by in silico methods. The compounds a (-F), b (-CF3), c (-Bis-CF3), d (-CH3), e (-OOH) and 4-PSQ exert antinociceptive effects in chemical and thermal nociception models, except compounds d (-CH3) and e (-OOH) that did not show antinociceptive effects in the hot plate test. In addition, treatments with all compounds did not cause locomotor changes in mice. In silico data  the compounds revealed that only compound c (Bis-CF3) exhibited low gastrointestinal absorption and that compounds c (Bis-CF3) and e (-OOH) do not have the ability to penetrate the blood-brain barrier, indicating that compound e (-OOH) did not produce a central antinociceptive effect. Furthermore, we found that this class of compounds has a higher affinity for COX-2 than for COX-1. In general, our data indicate that the insertion of substituents can alter the efficiency of 4-PSQ as an antinociceptive and anti-inflammatory agent.

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来源期刊
Chemistry & Biodiversity
Chemistry & Biodiversity 环境科学-化学综合
CiteScore
3.40
自引率
10.30%
发文量
475
审稿时长
2.6 months
期刊介绍: Chemistry & Biodiversity serves as a high-quality publishing forum covering a wide range of biorelevant topics for a truly international audience. This journal publishes both field-specific and interdisciplinary contributions on all aspects of biologically relevant chemistry research in the form of full-length original papers, short communications, invited reviews, and commentaries. It covers all research fields straddling the border between the chemical and biological sciences, with the ultimate goal of broadening our understanding of how nature works at a molecular level. Since 2017, Chemistry & Biodiversity is published in an online-only format.
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