当前位置：
X-MOL 学术
›
J. Org. Chem.
›
论文详情
Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
Design, Synthesis, and Evaluation of a Luminescent Cholesterol Mimic
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-12-28 , DOI: 10.1021/acs.joc.0c02460 Emily M Work 1 , Guillermo Ferraudi 2 , Luke Kiefer 1 , Gang Liu 1 , Michael Grigalunas 1 , Atul Bhardwaj 1 , Rasmin Kaur 3 , Janel M Dempsey 1 , Daniel Wüstner 3 , Paul Helquist 1 , Olaf Wiest 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-12-28 , DOI: 10.1021/acs.joc.0c02460 Emily M Work 1 , Guillermo Ferraudi 2 , Luke Kiefer 1 , Gang Liu 1 , Michael Grigalunas 1 , Atul Bhardwaj 1 , Rasmin Kaur 3 , Janel M Dempsey 1 , Daniel Wüstner 3 , Paul Helquist 1 , Olaf Wiest 1
Affiliation
|
The development of new chemical tools with improved properties is essential to chemical and cell biology. Of particular interest is the development of mimics of small molecules with important cellular function that allow the direct observation of their trafficking in a cell. To this end, a novel 15-azasterol has been designed and synthesized as a luminescent cholesterol mimic for the monitoring of cholesterol trafficking. The brightness of this probe, which is ∼32-times greater than the widely used dehydroergosterol probe, is combined with resistance to photobleaching in solution and in human fibroblasts and an exceptionally large Stokes-like shift of ∼150–200 nm. The photophysical properties of the probe have been studied experimentally and computationally, suggesting an intersystem crossing to the triplet excited state with subsequent phosphorescent decay. Molecular dynamics simulations show a similar binding mode of cholesterol and the azasterol probe to NPC proteins, demonstrating the structural similarity of the probe to cholesterol.
中文翻译：
发光胆固醇模拟物的设计、合成和评估
开发具有改进性能的新化学工具对于化学和细胞生物学至关重要。特别令人感兴趣的是具有重要细胞功能的小分子模拟物的开发，可以直接观察它们在细胞中的运输。为此，设计并合成了一种新型 15-氮杂甾醇作为发光胆固醇模拟物，用于监测胆固醇运输。该探针的亮度比广泛使用的脱氢麦角甾醇探针高约 32 倍，同时具有溶液和人类成纤维细胞中的抗光漂白性以及约 150-200 nm 的极大斯托克斯样位移。探针的光物理性质已经通过实验和计算进行了研究，表明系统间跨越到三重激发态并随后发生磷光衰变。分子动力学模拟显示胆固醇和氮杂甾醇探针与 NPC 蛋白具有相似的结合模式，证明了探针与胆固醇的结构相似性。
更新日期：2021-01-16
中文翻译：
发光胆固醇模拟物的设计、合成和评估
开发具有改进性能的新化学工具对于化学和细胞生物学至关重要。特别令人感兴趣的是具有重要细胞功能的小分子模拟物的开发，可以直接观察它们在细胞中的运输。为此，设计并合成了一种新型 15-氮杂甾醇作为发光胆固醇模拟物，用于监测胆固醇运输。该探针的亮度比广泛使用的脱氢麦角甾醇探针高约 32 倍，同时具有溶液和人类成纤维细胞中的抗光漂白性以及约 150-200 nm 的极大斯托克斯样位移。探针的光物理性质已经通过实验和计算进行了研究，表明系统间跨越到三重激发态并随后发生磷光衰变。分子动力学模拟显示胆固醇和氮杂甾醇探针与 NPC 蛋白具有相似的结合模式，证明了探针与胆固醇的结构相似性。
京公网安备 11010802027423号