• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

氘标记维生素 D 代谢物的合成作为 LC-MS 分析的内标。

Synthesis of Deuterium-Labeled Vitamin D Metabolites as Internal Standards for LC-MS Analysis.

机构信息

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.

Medical Equipment Business Operations, Management Strategy Planning Division, JEOL Ltd., Akishima, Tokyo 196-8558, Japan.

出版信息

Molecules. 2022 Apr 9;27(8):2427. doi: 10.3390/molecules27082427.

DOI:10.3390/molecules27082427
PMID:35458625
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9025501/
Abstract

Blood levels of the vitamin D (D) metabolites 25-hydroxyvitamin D (25(OH)D), 24,25-dihydroxyvitamin D, and 1α,25-dihydroxyvitamin D (1,25(OH)D) are recognized indicators for the diagnosis of bone metabolism-related diseases, D deficiency-related diseases, and hypercalcemia, and are generally measured by liquid-chromatography tandem mass spectrometry (LC-MS/MS) using an isotope dilution method. However, other D metabolites, such as 20-hydroxyvitamin D and lactone D, also show interesting biological activities and stable isotope-labeled derivatives are required for LC-MS/MS analysis of their concentrations in serum. Here, we describe a versatile synthesis of deuterium-labeled D metabolites using A-ring synthons containing three deuterium atoms. Deuterium-labeled 25(OH)D (), 25(OH)D-23,26-lactone (), and 1,25(OH)D-23,26-lactone () were synthesized, and successfully applied as internal standards for the measurement of these compounds in pooled human serum. This is the first quantification of 1,25(OH)D-23,26-lactone () in human serum.

摘要

血液中维生素 D(D)代谢物 25-羟维生素 D(25(OH)D)、24,25-二羟维生素 D 和 1α,25-二羟维生素 D(1,25(OH)D)的水平被认为是诊断与骨代谢相关的疾病、D 缺乏相关疾病和高钙血症的指标,通常采用液相色谱-串联质谱法(LC-MS/MS)并用同位素稀释法进行测量。然而,其他 D 代谢物,如 20-羟维生素 D 和内酯 D,也表现出有趣的生物活性,需要对其在血清中的浓度进行 LC-MS/MS 分析时使用稳定同位素标记的衍生物。在这里,我们描述了一种使用含有三个氘原子的 A 环合成子合成氘标记 D 代谢物的通用方法。合成了氘标记的 25(OH)D()、25(OH)D-23,26-内酯()和 1,25(OH)D-23,26-内酯(),并成功地将其用作这些化合物在混合人血清中测量的内标。这是首次对人血清中 1,25(OH)D-23,26-内酯()进行定量。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/3f6efb0f006a/molecules-27-02427-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/ca92ff8ddccd/molecules-27-02427-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/eaeacf7f0127/molecules-27-02427-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/96445efc2d89/molecules-27-02427-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/b56a4ee87403/molecules-27-02427-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/e6d1f09334e4/molecules-27-02427-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/c85c735ca69e/molecules-27-02427-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/c1dba0423650/molecules-27-02427-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/3f6efb0f006a/molecules-27-02427-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/ca92ff8ddccd/molecules-27-02427-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/eaeacf7f0127/molecules-27-02427-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/96445efc2d89/molecules-27-02427-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/b56a4ee87403/molecules-27-02427-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/e6d1f09334e4/molecules-27-02427-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/c85c735ca69e/molecules-27-02427-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/c1dba0423650/molecules-27-02427-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ede/9025501/3f6efb0f006a/molecules-27-02427-g005.jpg

相似文献

1
Synthesis of Deuterium-Labeled Vitamin D Metabolites as Internal Standards for LC-MS Analysis.氘标记维生素 D 代谢物的合成作为 LC-MS 分析的内标。
Molecules. 2022 Apr 9;27(8):2427. doi: 10.3390/molecules27082427.
2
Improved accuracy of an tandem liquid chromatography-mass spectrometry method measuring 24R,25-dihydroxyvitamin D and 25-hydroxyvitamin D metabolites in serum using unspiked controls and its application to determining cross-reactivity of a chemiluminescent microparticle immunoassay.使用未加标对照提高串联液相色谱 - 质谱法测定血清中24R,25 - 二羟基维生素D和25 - 羟基维生素D代谢物的准确性及其在化学发光微粒免疫测定交叉反应性测定中的应用
J Chromatogr A. 2017 May 12;1497:102-109. doi: 10.1016/j.chroma.2017.03.058. Epub 2017 Mar 23.
3
Interlaboratory comparison of 25-hydroxyvitamin D assays: Vitamin D Standardization Program (VDSP) Intercomparison Study 2 - Part 1 liquid chromatography - tandem mass spectrometry (LC-MS/MS) assays - impact of 3-epi-25-hydroxyvitamin D on assay performance.25-羟基维生素D检测方法的实验室间比对:维生素D标准化计划(VDSP)比对研究2 - 第1部分液相色谱 - 串联质谱(LC-MS/MS)检测方法 - 3-表-25-羟基维生素D对检测性能的影响
Anal Bioanal Chem. 2022 Jan;414(1):333-349. doi: 10.1007/s00216-021-03576-1. Epub 2021 Aug 25.
4
Candidate Reference Measurement Procedure for the Determination of (24R),25-Dihydroxyvitamin D3 in Human Serum Using Isotope-Dilution Liquid Chromatography-Tandem Mass Spectrometry.采用同位素稀释液相色谱-串联质谱法测定人血清中(24R),25-二羟基维生素D3的候选参考测量程序
Anal Chem. 2015 Aug 4;87(15):7964-70. doi: 10.1021/acs.analchem.5b01861. Epub 2015 Jul 24.
5
The serum vitamin D metabolome: What we know and what is still to discover.血清维生素 D 代谢组学:我们已知和未知的内容。
J Steroid Biochem Mol Biol. 2019 Feb;186:4-21. doi: 10.1016/j.jsbmb.2018.09.003. Epub 2018 Sep 8.
6
Simultaneous determination of 24,25- and 25,26-dihydroxyvitamin D3 in serum samples with liquid-chromatography mass spectrometry - A useful tool for the assessment of vitamin D metabolism.液相色谱-质谱联用法同时测定血清中 24,25-二羟维生素 D3 和 25,26-二羟维生素 D3——评估维生素 D 代谢的有用工具。
J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Nov 20;1158:122394. doi: 10.1016/j.jchromb.2020.122394. Epub 2020 Oct 6.
7
Interlaboratory comparison of 25-hydroxyvitamin D assays: Vitamin D Standardization Program (VDSP) Intercomparison Study 2 - Part 2 ligand binding assays - impact of 25-hydroxyvitamin D and 24R,25-dihydroxyvitamin D on assay performance.25-羟维生素 D 检测方法的实验室间比较:维生素 D 标准化项目(VDSP)比对研究 2-第 2 部分配体结合检测法 - 25-羟维生素 D 和 24R,25-二羟维生素 D 对检测性能的影响。
Anal Bioanal Chem. 2022 Jan;414(1):351-366. doi: 10.1007/s00216-021-03577-0. Epub 2021 Aug 25.
8
Clinical utility of simultaneous quantitation of 25-hydroxyvitamin D and 24,25-dihydroxyvitamin D by LC-MS/MS involving derivatization with DMEQ-TAD.采用DMEQ-TAD衍生化的液相色谱-串联质谱法同时定量测定25-羟基维生素D和24,25-二羟基维生素D的临床应用
J Clin Endocrinol Metab. 2014 Jul;99(7):2567-74. doi: 10.1210/jc.2013-4388. Epub 2014 Mar 26.
9
Development and validation of the simultaneous measurement of four vitamin D metabolites in serum by LC-MS/MS for clinical laboratory applications.用于临床实验室应用的液相色谱-串联质谱法同时测定血清中四种维生素D代谢物的方法开发与验证
Anal Bioanal Chem. 2016 Nov;408(27):7617-7627. doi: 10.1007/s00216-016-9821-4. Epub 2016 Aug 15.
10
High throughput LC-MS/MS method for the simultaneous analysis of multiple vitamin D analytes in serum.用于同时分析血清中多种维生素D分析物的高通量液相色谱-串联质谱法。
J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Mar 1;1014:56-63. doi: 10.1016/j.jchromb.2016.01.049. Epub 2016 Feb 2.

引用本文的文献

1
Natural Products Chemistry: Advances in Synthetic, Analytical and Bioactivity Studies.天然产物化学:合成、分析和生物活性研究的进展。
Molecules. 2023 Jul 22;28(14):5577. doi: 10.3390/molecules28145577.

本文引用的文献

1
Convergent total synthesis of (+)-calcipotriol: A scalable, modular approach to vitamin D analogs.(+)-钙泊三醇的汇聚全合成:维生素 D 类似物的可规模化、模块化方法。
Proc Natl Acad Sci U S A. 2022 May 3;119(18):e2200814119. doi: 10.1073/pnas.2200814119. Epub 2022 Apr 27.
2
Controlled lipid β-oxidation and carnitine biosynthesis by a vitamin D metabolite.维生素D代谢产物对脂质β-氧化和肉碱生物合成的调控
Cell Chem Biol. 2022 Apr 21;29(4):660-669.e12. doi: 10.1016/j.chembiol.2021.08.008. Epub 2021 Sep 9.
3
Differential diagnosis of vitamin D-related hypercalcemia using serum vitamin D metabolite profiling.
利用血清维生素 D 代谢产物谱对维生素 D 相关性高钙血症进行鉴别诊断。
J Bone Miner Res. 2021 Jul;36(7):1340-1350. doi: 10.1002/jbmr.4306. Epub 2021 May 10.
4
The Relative Expression of ERα Isoforms ERα66 and ERα36 Controls the Cellular Response to 24R,25-Dihydroxyvitamin D3 in Breast Cancer.雌激素受体α异构体 ERα66 和 ERα36 的相对表达控制乳腺癌细胞对 24R,25-二羟基维生素 D3 的反应。
Mol Cancer Res. 2021 Jan;19(1):99-111. doi: 10.1158/1541-7786.MCR-20-0169. Epub 2020 Oct 20.
5
A novel caged Cookson-type reagent toward a practical vitamin D derivatization method for mass spectrometric analyses.一种新型笼状 Cookson 型试剂,用于开发用于质谱分析的实用维生素 D 衍生化方法。
Rapid Commun Mass Spectrom. 2020 Apr 15;34(7):e8648. doi: 10.1002/rcm.8648.
6
24R,25-Dihydroxyvitamin D regulates breast cancer cells in vitro and in vivo.24R,25-二羟维生素 D 在体外和体内调节乳腺癌细胞。
Biochim Biophys Acta Gen Subj. 2019 Oct;1863(10):1498-1512. doi: 10.1016/j.bbagen.2019.05.013. Epub 2019 May 22.
7
Stereoselective Synthesis of Four Calcitriol Lactone Diastereomers at C23 and C25.23 位和 25 位差向立体选择性合成钙三醇内酯的四种非对映异构体。
J Org Chem. 2019 Jun 21;84(12):7630-7641. doi: 10.1021/acs.joc.9b00403. Epub 2019 Apr 24.
8
Clinical diagnostic tools for vitamin D assessment.维生素 D 评估的临床诊断工具。
J Steroid Biochem Mol Biol. 2018 Jun;180:105-117. doi: 10.1016/j.jsbmb.2017.10.003. Epub 2017 Oct 6.
9
Application of Cookson-type reagents for biomedical HPLC and LC/MS analyses: a brief overview.库克森型试剂在生物医学高效液相色谱和液相色谱/质谱分析中的应用:简要概述。
Biomed Chromatogr. 2017 Jan;31(1). doi: 10.1002/bmc.3808. Epub 2016 Sep 12.
10
Mass spectrometric profiling of vitamin D metabolites beyond 25-hydroxyvitamin D.25-羟基维生素D之外的维生素D代谢物的质谱分析
Clin Chem. 2015 Aug;61(8):1033-48. doi: 10.1373/clinchem.2015.241430. Epub 2015 Jun 30.