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细胞通透性 6-硝基二苯并呋喃基-笼状 IP3 的合成与表征。

Synthesis and characterization of cell-permeant 6-nitrodibenzofuranyl-caged IP3.

机构信息

Department of Neuroscience, Mount Sinai School of Medicine, New York, NY 10029, USA.

出版信息

Photochem Photobiol Sci. 2012 Mar;11(3):508-13. doi: 10.1039/c1pp05155e. Epub 2011 Aug 30.

DOI:10.1039/c1pp05155e
PMID:21879138
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4041591/
Abstract

We have synthesized in a 6-nitrodibenzofuranyl (NDBF) derivative of inositol-1,4,5-trisphosphate (IP(3)) for efficient two-photon uncaging in living cells. As its hexakis acetoxymethyl ester, this caged compound may be applied at low concentration to the extracellular milieu to load the intact astrocytes in acutely isolated brain slices from the mouse cortex. Two-photon irradiation of single astrocytes evoked intracellular calcium signals that required 10% of the energy dosage compared to nitroveratyl (NV)-IP(3). Since NDBF-IP(3) has a 5-fold higher quantum yield than NV-IP(3), these data imply that photolysis of the new NDBF caged compound mobilized intracellular calcium about twice as efficiently as the NV cage.

摘要

我们合成了 6-硝基金刚烷(NDBF)衍生的肌醇-1,4,5-三磷酸(IP(3)),用于在活细胞中进行高效的双光子光解。作为其六乙酰氧甲基酯,这种笼状化合物可以以低浓度应用于细胞外环境,以加载从小鼠皮层急性分离的脑片中完整的星形胶质细胞。双光子辐照单个星形胶质细胞引发的细胞内钙信号需要的能量剂量比硝基香草醛(NV)-IP(3)低 10%。由于 NDBF-IP(3)的量子产率比 NV-IP(3)高 5 倍,这些数据表明,新的 NDBF 笼状化合物的光解比 NV 笼状化合物更有效地动员细胞内钙约两倍。

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本文引用的文献

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2
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Wavelength-selective uncaging of dA and dC residues.选择性光解笼 dA 和 dC 残基。
Org Lett. 2011 Mar 18;13(6):1450-3. doi: 10.1021/ol200141v. Epub 2011 Feb 22.
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Probing nitrobenzhydrol uncaging mechanisms using FerriCast.使用 FerriCast 探测硝苯羟乙酮的解笼机制。
Org Lett. 2010 Oct 15;12(20):4486-9. doi: 10.1021/ol101726a.
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Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramidite.改进的双光子笼 3-硝基-2-乙基二苯并呋喃的合成及其在一种笼状胸腺嘧啶磷酰胺中的应用。
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