Analysis and determination of anti-diabetes drug acarbose and its structural analogs

Current Pharmaceutical Analysis

Volumn 7, Issue 1, 2011, Pages 12-20

  Wang, Ya Jun ^a   Zheng, Yu Guo ^a   Xue, Ya Ping ^a   Wang, Yuan Shan ^a   Shen, Yin Chu ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Acarbose; Analysis; Biosensor; Capillary electrophoresis; Diabetes; Liquid chromatography

Indexed keywords

ACARBOSE; CARBOHYDRATE DERIVATIVE;

ARTICLE; CAPILLARY ELECTROPHORESIS; DRUG DETERMINATION; DRUG SYNTHESIS; ENZYMIC BIOSENSOR; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIGHT SCATTERING; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REFRACTION INDEX; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 79952758020     PISSN: 15734129     EISSN: None     Source Type: Journal    
DOI: 10.2174/157341211794708721     Document Type: Article

References (53)

1. Josse, R.G.; Mcguire, A.J.; Saal, G.B. A review of the economic evidence for acarbose in the prevention of diabetes and cardiovascular events in individuals with impaired glucose tolerance. Int. J. Clin. Pract., 2006, 60, 847-855.
2. Delorme, S.; Chiasson, J.L. Acarbose in the prevention of cardiovascular disease in subjects with impaired glucose tolerance and type 2 diabetes mellitus. Curr. Opin. Pharmacol, 2005, 5, 184-189.
3. Wild, S.; Roglicm, G.; Green, A.; Sicree, R.; King, H. Global prevalence of diabetes: estimates for the year 2000 and projections for 2030. Diabetes Care, 2004, 27, 1047-1053.
4. King, H.; Aubert, R.E.; Herman, W.H. Global burden of diabetes, 1995-2025: prevalence, numerical estimates, and projections. Diabetes Care, 1998, 21, 1414-1431.
5. Coniff, R.; Krol, A. Acarbose: a review of US clinical experience. Clin. Ther., 1997, 19, 16-26.
6. Riley, M.D.; Blizzard, L. Comparative validity of a food frequency questionnaire for adults with IDDM. Diabetes Care, 1995, 18, 1249-1254.
7. Mahmud, T. The C7N aminocyclitol family of natural products. Nat. Prod. Rep., 2003, 20, 137-166.
8. Bowers, S.G.; Mahmud, T.; Floss, H.G. Biosynthetic studies on the a-glucosidase inhibitor acarbose: the chemical synthesis of dTDP- 4-amino-4,6-dideoxy-a-D-glucose. Carbohydr. Res.,2002,337,297-304.
9. Degwert, U.; Hülst, R.; Pape, H.; Herrold, R.E.; Beale, J.M.; Keller, P.J.; Lee, J.P.; Floss, H.G. Studies on the biosynthesis of the a-glucosidase inhibitor acarbose: Valienamine, a m-C7N unit not derived from the shikimate pathway. J. Antibiot., 1987, 40, 855-861.
10. Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D.D.; Wingender, W. Chemistry and biochemistry of microbial α-glucosidase inhibitors. Angew. Chem. Int. Ed. Engl, 1981, 20, 744-761.
11. Parenti, F.; Coronelli, C. Members of the genus Actinoplanes and their antibiotics. Annu. Rev. Microbiol, 1979, 33, 389-411.
12. Junge, B.; Heiker, F.R.; Kurz, J.; Müller, L.; Schmidt, D.D.; Wün-sche, C. Untersuchungen zur struktur des a-d-glucosidase inhibitors acarbose. Carbohyd. Res., 1984, 128, 235-268.
13. Mahmud, T.; Lee, S.; Floss, H.G. The biosynthesis of acarbose and validamycin. Chem. Rec, 2001, 1, 300-310.
14. Zheng, Y.G.; Shentu X.P.; Shen, Y.C. Inhibition of porcine small intestinal sucrase by valienamine. J. Enzyme Inhib. Med. Chem., 2005, 20, 49-53.
15. Zhang, J.F.; Zheng, Y.G.; Liu, Z.Q.; Shen, Y.C. Preparation of 3-ketovalidoxylamine A C-N lyase substrate: N-p-nitrophenyl-3-ketovalidamine by Stenotrophomonas maltrophilia CCTCC M 204024. Appl. Microbiol. Biotechnol, 2007, 73, 1275-1281.
16. Zheng, Y.G.; Xue, Y.P.; Shen, Y.C. Production of valienamine by a newly isolated strain: Stenotrophomonas maltrophilia. Enzyme Microb.Technol, 2006, 39, 1060-1065.
17. Zheng, Y.G.; Zhang, X.F.; Shen, Y.C. Microbial transformation of validamycin A to valienamine by immobilized cells. Biocatal Biotransform., 2005, 23, 71-77.
18. Chen, X.L.; Fan, Y.X.; Zheng, Y.G.; Shen, Y.C. Properties and Production of Valienamine and Its Related Analogues. Chem. Rev., 2003, 103, 1955-1977.
19. Chen, X.L.; Zheng, Y.G.; Shen, Y.C. A new method for production of valienamine with microbial degradation of acarbose. Biotechnol. Prog., 2005, 21, 1002-1003.
20. Xue, Y.P.; Zheng, Y.G.; Chen X.L.; Shen, Y.C. Quantitative determination of valienamine and validamine by thin-layer chromatography. J. Chromatogr. Sci., 2007, 45, 87-90.
21. Chen, X.L.; Zheng, Y.G.; Shen, Y.C. Quantitative analysis of valienamine in the microbial degradation of validamycin A after derivatization with p-nitrofluorobenzene by reversed-phase high-performance liquid chromatography. J. Chromatogr. B, 2005, 824, 341-347.
22. Bischoff, H. The mechanism of a-glucosidase inhibition in the management of diabetes. Clin. Invest. Med., 1995, 18, 303-311.
23. Chiasson, J.L.; Josse, R.G.; Gomis, R.; Hanefeld, M.; Karasik, A.; Laakso, M. Acarbose treatment and the risk of cardiovascular disease and hypertension in patients with impaired glucose tolerance: the STOP-NIDDM trial. J. Am. Med. Assoc, 2003, 290, 486-494.
24. Chiasson, J.L.; Josse, R.G.; Gomis, R.; Hanefeld, M.; Karasik, A.; Laakso, M. Acarbose for prevention of type 2 diabetes mellitus: the STOP-NIDDM randomised trial. Lancet, 2002, 359, 2072-2077.
25. Lebovitz, H.E. α-Glucosidase inhibitors as agents in the treatment of diabetes. Diabetes Rev., 1998, 6, 132-145.
26. Brunkhorst, C; Schneider, E. Characterization of maltose and maltotriose transport in the acarbose-producing bacterium Actinoplanes sp. Res. Microbiol, 2005, 156, 851-857.
27. Parche, S.; Schmid, R.; Titgemeyer, F. The phosphotransferase system (PTS) of Streptomyces coelicolor identification and biochemical analysis of a histidine phosphocarrier protein HPr encoded by the gene ptsH. Eur. J. Biochem., 1999, 265, 308-317.
28. Wehmeier, U.F.; Piepersberg, W. Biotechnology and molecular biology of the a-glucosidase inhibitor acarbose. Appl. Microbiol. Biotechnol, 2004, 63, 613-625.
29. th ed., Heparin Calcium, Optical Rotation, Council of Europe, Strasbourg, 2008, 1089-1091.
30. Hemker, M.; Stratmann, A.; Goeke, K.; Cchröder, W.; Lenz, J.; Piepersberg, W.; Pape, H. Identification, cloning, expression, and characterization of the extracellular acarbose-modifying glycosyltransferase, AcbD, from Actinoplanes sp. strain SE50. J. Bacteriol, 2001, 183, 4484-4492.
31. Schmidt, D.D.; Frommer, W.; Junge, B.; Müller, L.; Wingender, W.; Truscheit, E. a-Glucosidase inhibitors: new complex oligosaccharides of microbial origin. Naturwissenschaften, 1977, 64, 535-536.
32. Rodriguez, J.F.; De Lucas, A.; Carmona, M.; Cañas, F. Application of ion exchange to purify acarbose from fermentation broths. Biochem. Eng. J., 2008, 40, 130-137.
33. Choi, B.T.; Shin, C.S. Isolation and characterization of a novel intracellular glucosyltransferase from the acarbose producer Actinoplanes sp. CKD485-16. Appl Microbiol Biotechnol, 2004, 65, 273-280.
34. Choi, B.T.; Shin, C.S. Reduced formation of byproduct component C in acarbose fermentation by Actinoplanes sp. CKD485-16. Biotechnol Prog., 2003, 19,1677-1682
35. Almeling, S.; Holzgrabe, U. Use of evaporative light scattering detection for the quality control of drug substances: influence of different liquid chromatographic and evaporative light scattering detector parameters on the appearance of spike peaks. J. Chromatogr. A, 2010, 1217, 2163-2170.
36. Kohler, M.; Haerdi, W.; Christen P.; Veuthey, J.L. The evaporative light scattering detector: some applications in pharmaceutical analysis. Trends Analyt. Chem., 1997, 16, 475-484.
37. Cherkaoui, S.; Daali, Y.; Christen, P.; Veuthey, J.L. Development and validation of liquid chromatography and capillary electrophoresis methods for acarbose determination in pharmaceutical tablets. J. Pharm. Biomed. Anal, 1998, 18, 729-735.
38. Antonio, C; Larson, T.; Gilday, A.; Graham, I.; Bergström E.; Thomas-Oates, J. Quantification of sugars and sugar phosphates in Arabidopsis thaliana tissues using porous graphitic carbon liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. A, 2007, 1172, 170-178.
39. Novak, P.; Tepes, P.; Cindric, M.; Ilijas, M.; Dragojevic, S.; Mihaljevic, K. Combined use of liquid chromatography-nuclear magnetic resonance spectroscopy and liquid chromatography-mass spectrometry for the characterization of an acarbose degradation product. J. Chromatogr. A, 2004, 1033, 299-303.
40. Daali, Y.; Cherkaoui, S.; Cahours, X.; Varesio, E.; Veuthey, J.L. High performance liquid chromatography of acarbose and its metabolite on porous graphitic carbon column, J. Sep. Sci., 2002, 25, 280-284.
41. Guo, D.; Nashunchaoketu; Wang, J.H.; Liu, X.H.; Wu, S.H.; Zhao, X.M.; Yang, B.H. Simultaneous determination of four highly polar anti-diabetic drugs in Chinese traditional patent medicines using high performance liquid chromatography. Chin. J. Chromatogr., 2009, 27, 211-215.
42. Colin, H.; Eon, C; Guiochon, G. Modified carbon black in high-performance liquid chromatography. J. Chromatogr. A, 1976, 119, 41-54.
43. Colin, H.; Eon, C; Guiochon, G. Reversed-phase liquid-solid chromatography on modified carbon black. J. Chromatogr. A, 1976, 122, 223-242.
44. Colin, H.; Guiochon, G. Development and use of carbon adsorbents in high-performance liquid-solid chromatography: II. Reproducibility of carbon adsorbents and the influence of graphitization on their performance. J. Chromatogr. A, 1977, 137, 19-33.
45. Jabeen, R.; Payne, D.; Wiktorowicz, J.; Mohammad, A.; Petersen, J. Capillary electrophoresis and the clinical laboratory. Electrophoresis, 2006, 27, 2413-2438.
46. Baldwin, R.P. Electrochemical determination of carbohydrates: Enzyme electrodes and amperometric detection in liquid chromatography and capillary electrophoresis. J. Pharm. Biomed. Anal, 1999, 19, 69-81.
47. Soga, T.; Serwe, M. Determination of carbohydrates in food samples by capillary electrophoresis with indirect UV detection. Food Chem., 2000, 69, 339-344.
48. Kraly, J.; Fazal, M.A.; Schoenherr, R.M.; Bonn, R.; Harwood, M.M.; Turner, E.; Jones, M.; Dovichi, N.J. Bioanalytical applications of capillary electrophoresis. Anal. Chem., 2006, 78, 4097-4110.
49. Rethfeld, I.; Blaschke, G. Analysis of the antidiabetic drug acarbose by capillary electrophoresis. J. Chromatogr. B, 1997, 700, 249-253.
50. Cherkaoui, S.; Daali, Y.; Christen, P.; Veuthey, J.L. Development and validation of liquid chromatography and capillary electrophoresis methods for acarbose determination in pharmaceutical tablets. J. Pharm. Biomed. Anal, 1998, 18, 729-735.
51. Wagner G.; Guilbault G.G. (Eds.). Food Biosensor Analysis, Marcel-Dekker, New York, 1994.
52. Timur, S.; Anik, Ü. α-Glucosidase based bismuth film electrode for inhibitor detection. Anal. Chem. Acta, 2007, 598, 143-146.
53. Matsumoto, K.; Takayama, K.; Abesundara, K.J.M.; Matsui, T. Assay of αa-glucosidase inhibitory activity using flow-biosensor system. Anal. Chem. Acta, 2003, 479, 135-141.