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长链酒石酸二酰胺的合成与表征作为新型神经酰胺类似物。

Synthesis and characterization of long-chain tartaric acid diamides as novel ceramide-like compounds.

机构信息

Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes E.u.9., Budapest H-1092, Hungary.

出版信息

Molecules. 2010 Feb 5;15(2):824-33. doi: 10.3390/molecules15020824.

DOI:10.3390/molecules15020824
PMID:20335949
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6256927/
Abstract

Ceramides play a crucial role in the barrier function of the skin as well as in transmembrane signaling. In this study long aliphatic chain tartaric acid diamides able to replace ceramides in an in vitro model of the stratum corneum lipid matrix due to their similar physico-chemical properties were synthesized from diacetoxysuccinic anhydride in four steps. Their pro-apoptotic effect on fibroblast cells was also investigated.

摘要

神经酰胺在皮肤的屏障功能以及跨膜信号转导中起着至关重要的作用。在这项研究中,由于其相似的物理化学性质,从二乙酰琥珀酸酐出发,经四步反应合成了能够在角质层脂质基质的体外模型中替代神经酰胺的长链脂肪二酸二酰胺。还研究了它们对成纤维细胞的促凋亡作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2fde/6256927/3f9b1ca5be05/molecules-15-00824-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2fde/6256927/de186aab5ba2/molecules-15-00824-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2fde/6256927/2d331662dc02/molecules-15-00824-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2fde/6256927/3f9b1ca5be05/molecules-15-00824-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2fde/6256927/de186aab5ba2/molecules-15-00824-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2fde/6256927/2d331662dc02/molecules-15-00824-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2fde/6256927/3f9b1ca5be05/molecules-15-00824-g002.jpg

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本文引用的文献

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A PAMPA study of the permeability-enhancing effect of new ceramide analogues.一种新型神经酰胺类似物对 PAMPA 通透性的增强作用研究。
Chem Biodivers. 2009 Nov;6(11):1867-74. doi: 10.1002/cbdv.200900149.
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Topical delivery of lipophilic drugs from o/w Pickering emulsions.亲脂性药物从水包油型皮克林乳液的局部递送。
Int J Pharm. 2009 Apr 17;371(1-2):56-63. doi: 10.1016/j.ijpharm.2008.12.017. Epub 2008 Dec 24.
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Medicinal chemistry aspects of drug targets in sphingolipid metabolism.鞘脂代谢中药物靶点的药物化学方面
ChemMedChem. 2008 Apr;3(4):543-51. doi: 10.1002/cmdc.200700252.
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Cystein cathepsin and Hsp90 activities determine the balance between apoptotic and necrotic cell death pathways in caspase-compromised U937 cells.半胱氨酸组织蛋白酶和热休克蛋白90的活性决定了半胱天冬酶功能受损的U937细胞凋亡和坏死性细胞死亡途径之间的平衡。
Biochim Biophys Acta. 2007 Oct;1773(10):1546-57. doi: 10.1016/j.bbamcr.2007.07.003. Epub 2007 Jul 19.
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Chemical tools to investigate sphingolipid metabolism and functions.用于研究鞘脂代谢和功能的化学工具。
ChemMedChem. 2007 May;2(5):580-606. doi: 10.1002/cmdc.200600195.
6
Human skin penetration of sunscreen nanoparticles: in-vitro assessment of a novel micronized zinc oxide formulation.防晒纳米颗粒对人体皮肤的渗透:新型微粉化氧化锌制剂的体外评估。
Skin Pharmacol Physiol. 2007;20(3):148-54. doi: 10.1159/000098701. Epub 2007 Jan 17.
7
Mechanism of antitumor drug action assessed by cytometry.通过细胞计数法评估抗肿瘤药物作用机制。
Methods Cell Biol. 2004;75:257-305. doi: 10.1016/s0091-679x(04)75011-6.
8
Skin deep.肤浅的;表面的
Eur J Pharm Biopharm. 2004 Sep;58(2):291-9. doi: 10.1016/j.ejpb.2004.03.002.
9
Ceramide in apoptosis: an overview and current perspectives.细胞凋亡中的神经酰胺:综述与当前观点
Biochim Biophys Acta. 2002 Dec 30;1585(2-3):114-25. doi: 10.1016/s1388-1981(02)00331-1.
10
Structure of the skin barrier and its modulation by vesicular formulations.皮肤屏障的结构及其由囊泡制剂的调节作用。
Prog Lipid Res. 2003 Jan;42(1):1-36. doi: 10.1016/s0163-7827(02)00028-0.