High performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD) for the sensitive determination of hyaluronan oligosaccharides

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 988, Issue , 2015, Pages 106-115

  Rothenhöfer, Martin ^a   Grundmann, Marco ^a   Bernhardt, Günther ^a   Matysik, Frank Michael ^a   Buschauer, Armin ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Bovine testicular hyaluronidase; Capillary electrophoresis; High performance anion exchange chromatography; Hyaluronan oligosaccharides; Pulsed amperometric detection; Turbidimetric hyaluronidase assay

Indexed keywords

CAPILLARY ELECTROPHORESIS; HYALURONIC ACID; IONS; MAMMALS; MOLECULAR WEIGHT; OLIGOSACCHARIDES;

BOVINE TESTICULAR HYALURONIDASE; CETYLTRIMETHYLAMMONIUM BROMIDE; EXTRACELLULAR MATRIX COMPONENTS; HIGH-PERFORMANCE ANION-EXCHANGE CHROMATOGRAPHY; HYALURONAN; LOW MOLECULAR WEIGHT; PHYSICOCHEMICAL REACTIONS; PULSED AMPEROMETRIC DETECTION;

CHROMATOGRAPHY;

ACETIC ACID; CETRIMIDE; HYALURONIC ACID; HYALURONIDASE; HYALURONOGLUCOSAMINIDASE; OLIGOSACCHARIDE; SODIUM HYDROXIDE;

ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; ELECTROSPRAY; EXTRACELLULAR MATRIX; MOLECULAR WEIGHT; PRECIPITATION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; ANIMAL; BOVINE; CAPILLARY ELECTROPHORESIS; ION EXCHANGE CHROMATOGRAPHY; LIMIT OF DETECTION; MALE; METABOLISM; PH; PROCEDURES; REPRODUCIBILITY; STATISTICAL MODEL; TEMPERATURE;

BOVINAE;

ANIMALS; CATTLE; CETRIMONIUM COMPOUNDS; CHROMATOGRAPHY, ION EXCHANGE; ELECTROPHORESIS, CAPILLARY; HYALURONIC ACID; HYALURONOGLUCOSAMINIDASE; HYDROGEN-ION CONCENTRATION; LIMIT OF DETECTION; LINEAR MODELS; MALE; OLIGOSACCHARIDES; REPRODUCIBILITY OF RESULTS; SODIUM ACETATE; SODIUM HYDROXIDE; TEMPERATURE;

EID: 84924590723     PISSN: 15700232     EISSN: 1873376X     Source Type: Journal    
DOI: 10.1016/j.jchromb.2015.02.027     Document Type: Article

References (58)

1. Laurent T.C., Laurent U.B., Fraser J.R. The structure and function of hyaluronan: an overview. Immunol. Cell Biol. 1996, 74:A1-A7.
2. Chen W.Y., Abatangelo G. Functions of hyaluronan in wound repair. Wound Repair Regen. 1999, 7:79-89.
3. Noble P.W. Hyaluronan and its catabolic products in tissue injury and repair. Matrix Biol. 2002, 21:25-29.
4. Day A.J., de la Motte C.A. Hyaluronan cross-linking: a protective mechanism in inflammation?. Trends Immunol. 2005, 26:637-643.
5. de la Motte C., Nigro J., Vasanji A., Rho H., Kessler S., Bandyopadhyay S., Danese S., Fiocchi C., Stern R. Platelet-derived hyaluronidase 2 cleaves hyaluronan into fragments that trigger monocyte-mediated production of proinflammatory cytokines. Am. J. Pathol. 2009, 174:2254-2264.
6. Boregowda R.K., Appaiah H.N., Siddaiah M., Kumarswamy S.B., Sunila S., Thimmaiah K.N., Mortha K., Toole B., Banerjee S. Expression of hyaluronan in human tumor progression. J. Carcinog. 2006, 5:2.
7. Chao K.L., Muthukumar L., Herzberg O. Structure of human hyaluronidase-1, a hyaluronan hydrolyzing enzyme involved in tumor growth and angiogenesis. Biochemistry 2007, 46:6911-6920.
8. Novak U., Stylli S.S., Kaye A.H., Lepperdinger G. Hyaluronidase-2 overexpression accelerates intracerebral but not subcutaneous tumor formation of murine astrocytoma cells. Cancer Res. 1999, 59:6246-6250.
9. Stern R. Hyaluronan metabolism: a major paradox in cancer biology. Pathol. Biol. (Paris) 2005, 53:372-382.
10. Stern R. Hyaluronidases in cancer biology. Semin. Cancer Biol. 2008, 18:275-280.
11. Asari A. Novel functions of hyaluronan oligosaccharides. Glycoforum 2005, http://www.glycoforum.gr.jp/science/hyaluronan/HA12a/HA12aE.html.
12. Grundmann M., Rothenhöfer M., Bernhardt G., Buschauer A., Matysik F.M. Fast counter-electroosmotic capillary electrophoresis-time-of-flight mass spectrometry of hyaluronan oligosaccharides. Anal. Bioanal. Chem. 2012, 402:2617-2623.
13. Kühn A.V., Rüttinger H.H., Neubert R.H., Raith K. Identification of hyaluronic acid oligosaccharides by direct coupling of capillary electrophoresis with electrospray ion trap mass spectrometry. Rapid Commun. Mass Spectrom. 2003, 17:576-582.
14. Matsuno Y.K., Kakoi N., Kinoshita M., Matsuzaki Y., Kumada J., Kakehi K. Electrophoresis studies on the contaminating glycosaminoglycans in commercially available hyaluronic acid products. Electrophoresis 2008, 29:3628-3635.
15. Ikegami-Kawai M., Takahashi T. Microanalysis of hyaluronan oligosaccharides by polyacrylamide gel electrophoresis and its application to assay of hyaluronidase activity. Anal. Biochem. 2002, 311:157-165.
16. Bhilocha S., Amin R., Pandya M., Yuan H., Tank M., LoBello J., Shytuhina A., Wang W., Wisniewski H.G., de la Motte C., Cowman M.K. Agarose and polyacrylamide gel electrophoresis methods for molecular mass analysis of 5- to 500-kDa hyaluronan. Anal. Biochem. 2011, 417:41-49.
17. Cowman M.K., Chen C.C., Pandya M., Yuan H., Ramkishun D., LoBello J., Bhilocha S., Russell-Puleri S., Skendaj E., Mijovic J., Jing W. Improved agarose gel electrophoresis method and molecular mass calculation for high molecular mass hyaluronan. Anal. Biochem. 2011, 417:50-56.
18. Chen F., Kakizaki I., Yamaguchi M., Kojima K., Takagaki K., Endo M. Novel products in hyaluronan digested by bovine testicular hyaluronidase. Glycoconj. J. 2009, 26:559-566.
19. Tawada A., Masa T., Oonuki Y., Watanabe A., Matsuzaki Y., Asari A. Large-scale preparation, purification, and characterization of hyaluronan oligosaccharides from 4-mers to 52-mers. Glycobiology 2002, 12:421-426.
20. Alaniz L., Garcia M.G., Gallo-Rodriguez C., Agusti R., Sterin-Speziale N., Hajos S.E., Alvarez E. Hyaluronan oligosaccharides induce cell death through PI3-K/Akt pathway independently of NF-kappaB transcription factor. lycobiology 2006, 16:359-367.
21. Borromei C., Cavazza A., Corradini C., Vatteroni C., Bazzini A., Ferrari R., Merusi P. Validated HPAEC-PAD method for prebiotics determination in synbiotic fermented milks during shelf life. Anal. Bioanal. Chem. 2010, 397:127-135.
22. Borromei C., Cavazza A., Merusi C., Corradini C. Characterization and quantitation of short-chain fructooligosaccharides and inulooligosaccharides in fermented milks by high-performance anion-exchange chromatography with pulsed amperometric detection. J. Sep. Sci. 2009, 32:3635-3642.
23. Bruggink C., Maurer R., Herrmann H., Cavalli S., Hoefler F. Analysis of carbohydrates by anion exchange chromatography and mass spectrometry. J. Chromatogr. A 2005, 1085:104-109.
24. Cordella C.B., Militão J.S., Clément M.C., Cabrol-Bass D. Honey characterization and adulteration detection by pattern recognition applied on HPAEC-PAD profiles. 1. Honey floral species characterization. J. Agric. Food Chem. 2003, 51:3234-3242.
25. Der Agopian R.G., Soares C.A., Purgatto E., Cordenunsi B.R., Lajolo F.M. Identification of fructooligosaccharides in different banana cultivars. J. Agric. Food Chem. 2008, 56:3305-3310.
26. Liu Y., Jiang X.L., Cui H., Guan H.S. Analysis of oligomannuronic acids and oligoguluronic acids by high-performance anion-exchange chromatography and electrospray ionization mass spectrometry. J. Chromatogr. A 2000, 884:105-111.
27. Verspreet J., Pollet A., Cuyvers S., Vergauwen R., Van den Ende W., Delcour J.A., Courtin C.M. A simple and accurate method for determining wheat grain fructan content and average degree of polymerization. J. Agric. Food Chem. 2012, 60:2102-2107.
28. Zook C.M., LaCourse W.R. Pulsed amperometric detection of carbohydrates in fruit juices following high performance anion exchange chromatography. Curr. Sep. 1995, 14:48-52.
29. Behan J.L., Smith K.D. The analysis of glycosylation: a continued need for high pH anion exchange chromatography. Biomed. Chromatogr. 2011, 25:39-46.
30. Stadheim T.A., Li H., Kett W., Burnina I.N., Gerngross T.U. Use of high-performance anion exchange chromatography with pulsed amperometric detection for O-glycan determination in yeast. Nat. Protoc. 2008, 3:1026-1031.
31. De Plater G., Martin R.L., Milburn P.J. A pharmacological and biochemical investigation of the venom from the platypus (Ornithorhynchus anatinus). Toxicon 1995, 33:157-169.
32. Radva D., Knutsen S.H., Kosáry J., Ballance S. Application of high-performance anion-exchange chromatography with pulsed amperometric detection to compare the kinetic properties of beta-glucosidase on oligosaccharides from lichenase digested barley beta-glucan. Carbohydr. Res. 2012, 358:56-60.
33. Rodriguez-Colinas B., Poveda A., Jimenez-Barbero J., Ballesteros A.O., Plou F.J. Galacto-oligosaccharide synthesis from lactose solution or skim milk using the beta-galactosidase from Bacillus circulans. J. Agric. Food Chem. 2012, 60:6391-6398.
34. Iqbal S., Nguyen T.H., Nguyen T.T., Maischberger T., Haltrich D. Beta-galactosidase from Lactobacillus plantarum WCFS1: biochemical characterization and formation of prebiotic galacto-oligosaccharides. Carbohydr. Res. 2010, 345:1408-1416.
35. Weissmann B., Meyer K., Sampson P., Linker A. Isolation of oligosaccharides enzymatically produced from hyaluronic acid. J. Biol. Chem. 1954, 208:417-429.
36. Kakizaki I., Ibori N., Kojima K., Yamaguchi M., Endo M. Mechanism for the hydrolysis of hyaluronan oligosaccharides by bovine testicular hyaluronidase. FEBS J. 2010, 277:1776-1786.
37. Mahoney D.J., Aplin R.T., Calabro A., Hascall V.C., Day A.J. Novel methods for the preparation and characterization of hyaluronan oligosaccharides of defined length. Glycobiology 2001, 11:1025-1033.
38. Hoechstetter J. Characterisation of bovine testicular hyaluronidase and a hyaluronate lyase from Streptococcus agalactiae: investigations on the effect of pH on hyaluronan degradation and preclinical studies on the adjuvant administration of the enzymes in cancer chemotherapy. PhD Thesis 2005, University of Regensburg, http://epub.uni-regensburg.de/10330/.
39. Prebyl B.S., Kaczmarek C., Tuinman A.A., Baker D.C. Characterizing the electrospray-ionization mass spectral fragmentation pattern of enzymatically derived hyaluronic acid oligomers. Carbohydr. Res. 2003, 338:1381-1387.
40. Price K.N., Tuinman A., Baker D.C., Chisena C., Cysyk R.L. Isolation and characterization by electrospray-ionization mass spectrometry and high-performance anion-exchange chromatography of oligosaccharides derived from hyaluronic acid by hyaluronate lyase digestion: observation of some heretofore unobserved oligosaccharides that contain an odd number of units. Carbohydr. Res. 1997, 303:303-311.
41. Muckenschnabel I., Bernhardt G., Spruß T., Dietl B., Buschauer A. Quantitation of hyaluronidases by the Morgan-Elson reaction: comparison of the enzyme activities in the plasma of tumor patients and healthy volunteers. Cancer Lett. 1998, 131:13-20.
42. Reissig J.L., Storminger J.L., Leloir L.F. A modified colorimetric method for the estimation of N-acetylamino sugars. J. Biol. Chem. 1955, 217:959-966.
43. Hofinger E.S.A., Bernhardt G., Buschauer A. Kinetics of Hyal-1 and PH-20 hyaluronidases: comparison of minimal substrates and analysis of the transglycosylation reaction. Glycobiology 2007, 17:963-971.
44. Hofinger E.S.A., Hoechstetter J., Oettl M., Bernhardt G., Buschauer A. Isoenzyme-specific differences in the degradation of hyaluronic acid by mammalian-type hyaluronidases. Glycoconj. J. 2008, 25:101-109.
45. Di Ferrante N. Turbidimetric measurement of acid mucopolysaccharides and hyaluronidase activity. J. Biol. Chem. 1956, 220:303-306.
46. Clarke A.J., Sarabia V., Keenleyside W., MacLachlan P.R., Whitfield C. The compositional analysis of bacterial extracellular polysaccharides by high-performance anion-exchange chromatography. Anal. Biochem. 1991, 199:68-74.
47. Hotchkiss A.T., Hicks K.B. Analysis of oligogalacturonic acids with 50 or fewer residues by high-performance anion-exchange chromatography and pulsed amperometric detection. Anal. Biochem. 1990, 184:200-206.
48. Blundell C.D., Almond A. Enzymatic and chemical methods for the generation of pure hyaluronan oligosaccharides with both odd and even numbers of monosaccharide units. Anal. Biochem. 2006, 353:236-247.
49. Oettl M., Hoechstetter J., Asen I., Bernhardt G., Buschauer A. Comparative characterization of bovine testicular hyaluronidase and a hyaluronate lyase from Streptococcus agalactiae in pharmaceutical preparations. Eur. J. Pharm. Sci. 2003, 18:267-277.
50. Meyer K. The Enzymes 1971, 307-320. Academic Press, New York.
51. Vercruysse K.P., Lauwers A.R., Demeester J.M. Kinetic investigation of the degradation of hyaluronan by hyaluronidase using gel permeation chromatography. J. Chromatogr. B 1994, 656:179-190.
52. Deschrevel B., Tranchepain F., Vincent J.C. Chain-length dependence of the kinetics of the hyaluronan hydrolysis catalyzed by bovine testicular hyaluronidase. Matrix Biol. 2008, 27:475-486.
53. Cramer J.A., Bailey L.C., Bailey C.A., Miller R.T. Kinetic and mechanistic studies with bovine testicular hyaluronidase. Biochim. Biophys. Acta 1994, 1200:315-321.
54. Highsmith S., Garvin J.H., Chipman D.M. Mechanism of action of bovine testicular hyaluronidase. Mapping of the active site. J. Biol. Chem. 1975, 250:7473-7480.
55. Meyer K. The biological significance of hyaluronic acid and hyaluronidase. Physiol. Rev. 1947, 27:335-359.
56. Rapport M.M., Meyer K., Linker A. Correlation of reductimetric and turbidimetric methods for hyaluronidase assay. J. Biol. Chem. 1950, 186:615-623.
57. Min H., Cowman M.K. Combined alcian blue and silver staining of glycosaminoglycans in polyacrylamide gels: application to electrophoretic analysis of molecular weight distribution. Anal. Biochem. 1986, 155:275-285.
58. Rothenhöfer M., Scherübl R., Bernhardt G., Heilmann J., Buschauer A. Qualitative and quantitative analysis of hyaluronan oligosaccharides with high performance thin layer chromatography using reagent-free derivatization on amino-modified silica and electrospray ionization-quadrupole time-of-flight mass spectrometry coupling on normal phase. J. Chromatogr. A 2012, 1248:169-177.