Profiling of chiral and achiral carboxylic acid metabolomics: synthesis and evaluation of triazine-type chiral derivatization reagents for carboxylic acids by LC-ESI-MS/MS and the application to saliva of healthy volunteers and diabetic patients

详细信息    查看全文

• 作者：Takahiro Takayama (1)
  Tomohiro Kuwabara (1)
  Toshio Maeda (2)
  Ichiro Noge (3)
  Yutaka Kitagawa (4)
  Koichi Inoue (1)
  Kenichiro Todoroki (1)
  Jun Zhe Min (1)
  Toshimasa Toyo鈥檕ka (1)
  
  1. Laboratory of Analytical and Bio-Analytical Chemistry ; School of Pharmaceutical Sciences ; University of Shizuoka ; 52-1 Yada ; Suruga-ku ; Shizuoka ; 422-8526 ; Japan
  2. Laboratory of Clinical Pharmaceutics and Pharmacy Practice ; School of Pharmaceutical Sciences ; University of Shizuoka ; 52-1 Yada ; Suruga-ku ; Shizuoka ; 422-8526 ; Japan
  3. Department of Pharmaceutical ; Numazu City Hospital ; Harunoki Higashi-Shiizi ; Numazu ; 410-0302 ; Japan
  4. Department of Clinical and Molecular Endocrinology ; Numazu City Hospital ; Harunoki Higashi-Shiizi ; Numazu ; 401-0302 ; Japan
  
• 关键词：Chiral metabolomics ; Carboxylic acids ; Chiral derivatization reagent ; Enantiomer separation ; UPLC ; MS/MS ; Saliva analysis ; Diabetic patients
• 刊名：Analytical and Bioanalytical Chemistry
• 出版年：2015
• 出版时间：January 2015
• 年：2015
• 卷：407
• 期：3
• 页码：1003-1014
• 全文大小：844 KB
• 参考文献：1. Vinayavekhin N, Homan EA, Saghatelian A (2010) ACS Chem Biol 5:91鈥?03 CrossRef
  2. Nishikawa T (2005) Biol Pharm Bull 28:1561鈥?565 561" target="_blank" title="It opens in new window">CrossRef
  3. Sasabe S, Chiba T, Yamada M, Okamoto K, Nishimoto I, Matsuoka M, Aiso S (2007) EMBO J 26:4149鈥?159 CrossRef
  4. Tsai GE, Yang P, Chang YC, Chong MY (2006) Biol Psychiatry 59:230鈥?34 5.06.032" target="_blank" title="It opens in new window">CrossRef
  5. Wadleigh SDD, McMahon FJ (2006) Biol Psychiatry 60:106鈥?09 CrossRef
  6. Murray ED Jr, Wechter WJ, Kantoci D, Wang WH, Pham T, Quiggle DD, Gibson KM, Leipold D, Anner BM (1997) J Pharmacol Exp Ther 282:657鈥?62
  7. Toyo'oka T (2008) J Chromatogr Sci 46:233鈥?47 CrossRef
  8. Toyo鈥檕ka T (1999) Modern derivatization methods for separation sciences, Toyo鈥檕ka T (ed) Wiley, Chichester, UK, pp 217-289
  9. Waldhier MC, Almstetter MF, Nurnberger N, Gruber MA, Dettmer K, Oefner PJ (2011) J Chromatogr A 1218:4537鈥?544 5.039" target="_blank" title="It opens in new window">CrossRef
  10. Simek P, Husek P, Zahradnickova H, Amino acid analysis (Ed. Alterman MA and Hunziker P), Methods in Mol Biol 828 (2012) Capter 13:137鈥?52
  11. Podebrad F, Heil M, Leib S, Geier B, Beck T, Mosandl A, Sewell AC, Bohles H (1997) J High Res Chromatogr 20:355鈥?62 CrossRef
  12. Tsutsui H, Fujii S, Sakamoto T, Min JZ, Todoroki K, Toyo'oka T (2012) J Sep Sci 35:1551鈥?559 CrossRef
  13. Higashi T, Kawasaki M, Tadokoro H, Ogawa S, Tsutsui H, Fukushima T, Toyo'oka T (2012) J Sep Sci 35:2840鈥?846 585" target="_blank" title="It opens in new window">CrossRef
  14. Nagao R, Tsutsui H, Mochizuki T, Takayama T, Kuwabara T, Min JZ, Inoue K, Todoroki K, Toyo'oka T (2013) J Chromatogr A 1296:111鈥?18 CrossRef
  15. Kuwabara T, Takayama T, Todoroki K, Inoue K, Min JZ, Toyo'oka T (2014) Anal Bioanal Chem 406:2641鈥?649 CrossRef
  16. Bogusz MJ (1999) J Chromatogr B 733:65鈥?1 520-9" target="_blank" title="It opens in new window">CrossRef
  17. Marquet P, Lachatre G (1999) J Chromatogr B 733:93鈥?18 CrossRef
  18. Niessen WMA (1998) J Chromatogr A 794:407鈥?35 CrossRef
  19. Iwasaki Y, Nakano Y, Mochizuki K, Nomoto M, Takahashi Y, Ito R, Saito K, Nakazawa H (2011) J Chromtogr B 879:1159鈥?165 CrossRef
  20. Johnson DW (2005) Clin Biochem 38:351鈥?61 5.01.007" target="_blank" title="It opens in new window">CrossRef
  21. Gagne S, Crane S, Huang Z, Li CS, Bateman KP, Levesque JF (2007) J Lipid Res 48:252鈥?59 CrossRef
  22. Cartwright AJ, Jones P, Wolff JC, Evans EH (2005) Rapid Commun Mass Spectrom 19:1058鈥?062 CrossRef
  23. Higashi H, Ichikawa T, Inagaki S, Min JZ, Fukushima T, Toyo'oka T (2010) J Pharm Biomed Anal 52:809鈥?18 CrossRef
  24. Higashi H, Shibayama Y, Ichikawa T, Ito K, Toyo'oka T, Shimada K, Mitamura K, Ikegawa S, Chiba H (2010) Steroids 75:338鈥?45 5" target="_blank" title="It opens in new window">CrossRef
  25. Zhang D, Li W, Zhang J, Tang W, Qian C, Feng M, Chu Q, Ye J (2011) Anal Chim Acta 694:61鈥?6 CrossRef
  26. Chiappin S, Antonell G, Gatti R, De Palo EF (2007) Clin Chim Acta 383:30鈥?0 CrossRef
  27. Gr枚schl M (2008) Clin Chem 54:1759鈥?769 CrossRef
  28. Tsutsui H, Mochizuki T, Maeda T, Noge I, Kitagawa Y, Min JZ, Todoroki K, Inoue K, Toyo'oka T (2012) Anal Bioanal Chem 404:1925鈥?934 CrossRef
  29. Hasegawa H, Fukushima T, Lee J-A, Tsukamoto K, Moriya K, Ono Y, Imai K (2003) Anal Bioanal Chem 377:886鈥?91 CrossRef
  30. Nagata Y, Higashi M, Ishii Y, Sano H, Tanigawa M, Nagata K, Noguchi K, Urade M (2006) Life Sci 78:1677鈥?681 5.08.009" target="_blank" title="It opens in new window">CrossRef
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Analytical Chemistry
  Food Science
  Inorganic Chemistry
  Physical Chemistry
  Monitoring, Environmental Analysis and Environmental Ecotoxicology
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1618-2650

文摘

Novel triazine-type chiral derivatization reagents, i.e., (S)-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)pyrrolidin-3-amine (DMT-3(S)-Apy) and (S)-4,6-dimethoxy-N-(pyrrolidin-3-yl)-1,3,5-triazin-2-amine (DMT-1(S)-Apy), were developed for the highly sensitive and selective detection of chiral carboxylic acids by UPLC-MS/MS analysis. Among the synthesized reagents, DMT-3(S)-Apy was a more efficient chiral reagent for the enantiomeric separation of chiral carboxylic acids in terms of separation efficiency by reversed-phase chromatography and detection sensitivity by ESI-MS/MS. The DMT-3(S)-Apy was used for the determination of 13 carboxylic acids in human saliva of healthy volunteers and diabetic patients. Various biological carboxylic acids including chiral carboxylic acids, and mono- and di-carboxylic acids were clearly identified in the saliva of healthy persons and diabetic patients. The concentrations of carboxylic acids detected in the saliva of diabetic patients were relatively higher than those in the healthy persons. Furthermore, the concentration of d-lactic acid (LA) and the ratio of d/l-LA in the diabetic patients were significantly higher than those in the healthy persons. The low ratio of d/l-LA in healthy persons was also identified to be independent of age and sex. These results suggest that the determination of the d/l-LA ratio in saliva might be applicable for the diagnosis of diabetes. Based on these observations, DMT-3(S)-Apy seems to be a useful chiral derivatization reagent for the determination not only of chiral carboxylic acids but also achiral ones. In conclusion, the proposed method using DMT-3(S)-Apy is useful for the carboxylic acid metabolomics study of various specimens. Graphical Abstract DL-Lactic acids in saliva