N-(4′-吡哆氧基)鞘氨醇的合成及其在离体细胞中的摄取和代谢。

Z Zhang, E Smith, S M Surowiec, A H Merrill, D B McCormick
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引用次数: 6

摘要

合成了N-(4′-吡哆醇基)鞘氨醇,并将其定性为一种稳定的生物活性脂质递送化合物。人们发现它很容易被肝细胞吸收,尽管它的吸收机制比天然维生素B6所使用的机制更典型。一些N-(4'-吡哆醇)鞘醇在细胞内代谢作用释放吡哆醛5'-磷酸和鞘醇,但与天然维生素形式的B6相比,合成化合物的吡哆醛5'-磷酸的形成较差,这可能部分是由于细胞膜内的包裹以及负责维生素磷酸化的胞质吡哆醛激酶水平的限制。与母体长链碱基不同,B6缀合物没有特别的细胞毒性。此外,该化合物既不是人类中性粒细胞呼吸爆发的激活剂也不是抑制剂。这些发现确定了N-(4'-吡哆醇)鞘氨醇是研究维生素B6和鞘氨醇的细胞运输、代谢和功能的一个有趣的工具。
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Synthesis of N-(4'-pyridoxyl)sphingosine and its uptake and metabolism by isolated cells.

N-(4'-pyridoxyl)sphingosine was synthesized and characterized as a stable compound for specialized delivery of a bioactive lipid. It was found to be facilely taken up by hepatocytes although by a mechanism more typical for lipids than the one used by natural vitamin B6. Some of the N-(4'-pyridoxyl)sphingosine was metabolically acted upon inside the cell to release pyridoxal 5'-phosphate and sphingosine, but formation of pyridoxal 5'-phosphate from the synthetic compound was poor compared with natural vitamin forms of B6, which may partly be due to entrapment within cell membranes and to constraints at the level of cytosolic pyridoxal kinase which is responsible for phosphorylation of the vitamin. Unlike the parent long-chain base, the B6 conjugate was not particularly cytotoxic. Furthermore, the compound was neither an activator nor inhibitor of the respiratory burst of human neutrophils. These findings identify N-(4'-pyridoxyl)sphingosine as an interesting tool for studies of the cellular transport, metabolism, and functions of both vitamin B6 and sphingosine.

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