Advances in the Analysis of Chondroitin/Dermatan Sulfate

Advances in Pharmacology

Volumn 53, Issue , 2006, Pages 141-166

  Stylianou, M ^a   Triantaphyllidou, I E ^a   Vynios, D H ^a  

^a UNIVERSITY OF PATRAS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

CHONDROITIN SULFATE; DERMATAN SULFATE;

ELECTROPHORESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; GEL CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOHISTOCHEMISTRY; ION EXCHANGE CHROMATOGRAPHY; REVIEW;

CHONDROITIN SULFATES; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, ION EXCHANGE; DERMATAN SULFATE; ELECTROPHORESIS; ENZYME-LINKED IMMUNOSORBENT ASSAY; IMMUNOHISTOCHEMISTRY;

EID: 33846140856     PISSN: 10543589     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1054-3589(05)53007-2     Document Type: Review

References (99)

1. Bitter T., and Muir H.M. A modified uronic acid-carbazole reaction. Anal. Biochem. 4 (1962) 330-334
2. Björnsson S. Size dependent separation of proteoglycans by electrophoresis in gels of pure agarose. Anal. Biochem. 210 (1993) 282-291
3. Calabro A., Hascall V.C., and Midura R.J. Adaptation of FACE methodology for microanalysis of total hyaluronan and chondroitin sulfate composition from cartilage. Glycobiology 10 (2000) 283-293
4. Calabro A., Midura R., Wang A., West L., Plaas A., and Hascall V.C. Fluorophore-assisted carbohydrate electrophoresis (FACE) of glycosaminoglycans. Osteoarthritis Cartilage 9 Suppl A (2001) S16-S22
5. Capon C., Mizon C., Lemoine J., Rodie-Talbere P., and Mizon J. In acute inflammation, the chondroitin-4 sulphate carried by bikunin is not only longer, it is also undersulphated. Biochimie 85 (2003) 101-107
6. Carney S.L., and Muir H. The structure and function of cartilage proteoglycans. Physiol. Rev. 68 (1988) 858-910
7. Carulli D., Laabs T., Geller H.M., and Fawcett J.W. Chondroitin sulfate proteoglycans in neural development and regeneration. Curr. Opin. Neurobiol. 15 (2005) 116-120
8. Caterson B., Christner J.E., Baker J.R., and Couchman J.R. Production and characterization of monoclonal antibodies directed against connective tissue proteoglycans. Fed. Proc. 44 (1985) 386-393
9. Chan F.L., Choi H.L., and Underhill C.B. Hyaluronan and chondroitin sulfate proteoglycans are colocalized to the ciliary zonule of the rat eye: A histochemical and immunocytochemical study. Histochem. Cell Biol. 107 (1997) 289-301
10. Cöster L., Fransson L.A., Sheehan J., Nieduszynski I.A., and Phelps C.F. Self-association of dermatan sulphate proteoglycans from bovine sclera. Biochem. J. 197 (1981) 483-490
11. Couchman J.R., Caterson B., Christner J.E., and Baker J.R. Mapping by monoclonal antibody detection of glycosaminoglycans in connective tissues. Nature 307 (1984) 650-652
12. De Muro P., Faedda R., Formato M., Re F., Satta A., Cherchi G.M., and Carcassi A. Urinary glycosaminoglycans in patients with systemic lupus erythematosus. Clin. Exp. Rheumatol. 19 (2001) 125-130
13. Detamore M.S., Orfanos J.G., Almarza A.J., French M.M., Wong M.E., and Athanasiou K.A. Quantitative analysis and comparative regional investigation of the extracellular matrix of the porcine temporomandibular joint disc. Matrix Biol. 24 (2005) 45-57
14. Dietrich C.P., McDuffie N., and Sampaio L.O. Identification of acidic mucopolysaccharides by agarose gel electrophoresis. J. Chromatogr. 130 (1977) 299-304
15. Domowicz M., Mangoura D., and Schwartz N.B. Cell specific-chondroitin sulfate proteoglycan expression during CNS morphogenesis in the chick embryo. Int. J. Dev. Neurosci. 18 (2000) 629-641
16. Domowicz M.S., Mueller M.M., Novak T.E., Schwartz L.E., and Schwartz N.B. Developmental expression of the HNK-1 carbohydrate epitope on aggrecan during chondrogenesis. Dev. Dyn. 226 (2003) 42-50
17. Elson L.A., and Morgan W.T.J. A colorimetric method for the determination of glucosamine and chondrosamine. Biochem. J. 27 (1933) 1824-1933
18. Farndale R.W., Sayers C.A., and Barrett A.J. A direct spectophotometric microassay for sulphated glycosaminoglycans in cartilage cultures. Connect. Tissue Res. 9 (1982) 274-278
19. Farndale R.W., Buttle D.J., and Barrett A.J. Improved quantitation and discrimination of sulphated glycosaminoglycans by use of dimethylmethylene blue. Biochim. Biophys. Acta 883 (1986) 173-177
20. Fransson L.A., Cöster L., Malmström A., and Sheehan J.K. Self-association of scleral proteodermatan sulfate: Evidence for interaction via the dermatan sulfate side chains. J. Biol. Chem. 257 (1982) 6333-6338
21. Gao N. Fluorophore-assisted carbohydrate electrophoresis a: A sensitive and accurate method for the direct analysis of dolichol pyrophosphate-linked oligosaccharides in cell cultures and tissues. Methods 35 (2005) 323-327
22. Grigoreas G.H., Anagnostides S.T., and Vynios D.H. A solid-phase assay for the quantitative analysis of hyaluronic acid at the nanogram level. Anal. Biochem. 320 (2003) 179-184
23. Hardingham T.E., Fosang A.J., and Dudhia J. The structure, function and turnover of aggrecan, the large aggregating proteoglycan from cartilage. Eur. J. Clin. Chem. Clin. 32 (1994) 249-257
24. Hardingham T.E., Fosang A.J., Hey N.J., Hazell P.K., Kee W.J., and Ewins R.J. The sulphation pattern in chondroitin sulphate chains investigated by chondroitinase ABC and ACII digestion and reactivity with monoclonal antibodies. Carbohydr. Res. 255 (1994) 241-254
25. Hata R., and Nagai Y. A rapid and micro method for the separation of acidic glycosaminoglycans by two-dimensional electrophoresis. Anal. Biochem. 45 (1972) 462-468
26. Hata R., and Nagai Y. A micro colorimetric determination of acidic glycosaminoglycans by two-dimensional electrophoresis on a cellulose acetate strip. Anal. Biochem. 52 (1973) 652-656
27. Hayes M.L., and Castellino F.J. Carbohydrate of the human plasminogen variants. III. Structure of the O-glycosidically linked oligosaccharide unit. J. Biol. Chem. 254 (1979) 8777-8780
28. Herbert D., Phipps P.J., and Strange R.E. Clinical analysis of microbial cells. Methods Enzymol. 5B (1971) 209-344
29. Hjerpe A., Antonopoulos C.A., Classon B., and Engfeldt B. Separation and quantitative determination of galactosamine and glucosamine at the nanogram level by sulphonyl chloride reaction and high-performance liquid chromatography. J. Chromatogr. A 202 (1980) 453-459
30. Honda S., Konishi T., Suzuki S., Takahashi M., Kakehi K., and Ganno S. Automated analysis of hexosamines by high-performance liquid chromatography with photometric and fluorimetric postcolumn labeling using 2-cyanoacetamide. Anal. Biochem. 134 (1983) 483-488
31. Immers J., and Vasseur E. Influence of sugars and amines on the colorimetric hexosamine method of Elson and Morgan and its possible climination. Nature 165 (1950) 898-899
32. Inazumi T., Tajima S., and Nishikawa T. Overexcretion of low-sulphated chondroitin sulphate in the urine of the patient resembling progeroid. Dermatology 195 (1997) 296-300
33. Iozzo R.V. The family of the small leucine-rich proteoglycans: Key regulators of matrix assembly and cellular growth. Crit. Rev. Biochem. Mol. Biol. 32 (1997) 141-174
34. Iozzo R.V., and Clark C.C. Chondroitin sulfate proteoglycan is a constituent of the basement membrane in the rat embryo parietal yolk sac. Histochemistry 88 (1987) 23-29
35. Jackson P. The analysis of fluorophore-labeled carbohydrates by polyacrylamide gel electrophoresis. Mol. Biotechnol. 2 (1996) 101-123
36. Jang J.H., Hia H.C., Ike M., Inoue C., Fujita M., and Yoshida T. Acid hydrolysis and quantitative determination of total hexosamines of an exopolysaccharide produced by Citrobacter sp. Biotechnol. Lett. 27 (2005) 13-18
37. Johansson B., Smedberg J.-I., Langley M., and Embery G. Glycosaminoglycans in peri-implant sulcus fluid from implants placed in Martin sinus-inlay bone grafts. Clin. Oral Implants Res. 12 (2001) 202-206
38. Johnson W.E., Caterson B., Eisenstein S.M., and Roberts S. Human intervertebral disc aggrecan inhibits endothelial cell adhesion and cell migration in vitro. Spine 30 (2005) 1139-1147
39. Karamanos N.K., Syrokou A., Vanky P., Nurminen M., and Hjerpe A. Determination of 24 variously sulfated galactosaminoglycan- and hyaluronan-derived disaccharides by high-performance liquid chromatography. Anal. Biochem. 221 (1994) 189-199
40. Karamanos N.K., Vanky P., Syrokou A., and Hjerpe A. Identity of dermatan and chondroitin sequences in dermatan sulfate chains determined by using fragmentation with chondroitinases and ion-pair high-performance liquid chromatography. Anal. Biochem. 225 (1995) 220-230
41. Karamanos N.K., Axelsson S., Vanky P., Tzanakakis G.N., and Hjerpe A. Determination of hyaluronan and galactosaminoglycan disaccharides by high-performance capillary electrophoresis at the attomole level: Applications to analyses of tissue and cell culture proteoglycans. J. Chromatogr. A 696 (1995) 295-305
42. Karamanos N.K., Vanky P., Tzanakakis G.N., Tsegenidis T., and Hjerpe A. Ion-pair high performance liquid chromatography for determining disaccharide composition of heparin and heparan sulfate. J. Chromatogr. A 756 (1997) 169-179
43. Karlsson M., and Björnsson S. Quantitation of proteoglycans in biological fluids using Alcian blue. Methods Mol. Biol. 171 (2001) 159-173
44. Karousou E.G., Militsopoulou M., Porta G., DeLuca G., Hascall V.C., and Passi A. Polyacrylamide gel electrophoresis of fluorophore-labeled hyaluronan and chondroitin sulfate disaccharides: Application to the analysis in cells and tissues. Electrophoresis 25 (2004) 2919-2925
45. Karousou E.G., Viola M., Genasetti A., Vigetti D., DeLuca G., Karamanos N.K., and Passi A. Application of polyacrylamide gel electrophoresis of fluorophore-labeled saccharides for analysis of hyaluronan and chondroitin sulfate in human and animal tissues and cell cultures. Biomed. Chromatogr. 19 (2005) 761-765
46. Kinoshita A., Yamada S., Haslam S.M., Morris H.R., Dell A., and Sugahara K. Isolation and structural determination of novel sulfated hexasaccharides from squid cartilage chondroitin sulfate E that exhibits neuroregulatory activities. Biochemistry 40 (2001) 12654-12665
47. Kinsella M.G., Bressler S.L., and Wight T.N. The regulated synthesis of versican, decorin, and biglycan: Extracellular matrix proteoglycans that influence cellular phenotype. Crit. Rev. Eukaryot. Gene Expr. 14 (2004) 203-234
48. Kohler G., and Milstein C. Derivation of specific antibody-producing tissue culture and tumor lines by cell fusion. Eur. J. Immunol. 6 (1976) 511-519
49. Kokenyesi R. Ovarian carcinoma cells synthesize both chondroitin sulfate and heparan sulfate cell surface proteoglycans that mediate cell adhesion to interstitial matrix. J. Cell Biochem. 83 (2001) 259-270
50. Kresse H., Hauser H., and Schönherr E. Small proteoglycans. Experientia 49 (1993) 403-416
51. Kresse H., Hausser H., Schonherr E., and Bittner K. Biosynthesis and interactions of small chondroitin/dermatan sulphate proteoglycans. Eur. J. Clin. Chem. Clin. 32 (1994) 259-264
52. Lamari F., Theocharis A., Hjerpe A., and Karamanos N.K. Ultrasensitive capillary electrophoresis of sulfated disaccharides in chondroitin/dermatan sulfates by laser-induced fluorescence after derivatization with 2-aminoacridone. J. Chromatogr. B Biomed Sci. Appl. 730 (1999) 129-133
53. Lauder R.M., Huckerby T.N., and Nieduszynski I.A. A fingerprinting method for chondroitin/dermatan sulphate and hyaluronanoligosaccharides. Glycobiology 10 (2000) 393-401
54. Maccari F., and Volpi N. Direct and specific recognition of glycosaminoglycans by antibodies after their separation by agarose gel electrophoresis and blotting on cetylpyridinium chloride-treated nitrocellulose membranes. Electrophoresis 24 (2003) 1347-1352
55. Mastrogianni O., Lamari F., Syrokou A., Militsopoulou M., Hjerpe A., and Karamanos N.K. Microemulsion electrokinetic capillary chromatography of sulfated disaccharides derived from glycosaminoglycans. Electrophoresis 22 (2001) 2743-2745
56. Masuda T., and Shiga T. Chemorepulsion and cell adhesion molecules in patterning initial trajectories of sensory axons. Neurosci. Res. 51 (2005) 337-347
57. McDevitt C.A., and Muir H. Gel electrophoresis of proteoglycans and glycosaminoglycans on large-pore composite polyacrylamide-agarose gels. Anal. Biochem. 44 (1971) 612-622
58. Michaelsen S., Schroder M.B., and Sorensen H. Separation and determination of glycosaminoglycan disaccharides by micellar electrokinetic capillary chromatography for studies of pelt glycosaminoglycans. J. Chromatogr. A 652 (1993) 503-515
59. Mielke Jr. C.H., Starr C.M., Klock J.C., Devereaux D., Mielke M.R., Baker D.E., Broemeling L., Wacksman M., White Jr. J.R., Oliver S.A., Ens G., Gavin P., et al. Direct measurement of unfractionated heparin using a biochemical assay. Clin. Appl. Thromb. Hemost. 5 (1999) 267-276
60. Mitropoulou T.N., Lamari F., Syrokou A., Hjerpe A., and Karamanos N.K. Identification of oligomeric domains within dermatan sulfate chains using differential enzymic treatments, derivatization with 2-aminoacridone and capillary electrophoresis. Electrophoresis 22 (2001) 2458-2463
61. Mitropoulou T.N., and Stagiannis K.D. Variation in sulfation pattern of galactosaminoglycan containing proteoglycans is associated with the development of uterine leiomyoma. Biomed. Chromatogr. 18 (2004) 411-413
62. Mitropoulou T.N., Theocharis A.D., Stagiannis K.D., and Karamanos N.K. Identification, quantification and fine structural characterization of glycosaminoglycans from uterine leiomyoma and normal myometrium. Biochimie 83 (2001) 529-536
63. Nadanaka S., and Sugahara K. The unusual tetrasaccharide sequence GlcA beta 1-3GalNAc(4-sulfate)beta 1-4GlcA(2-sulfate)beta 1-3GalNAc(6-sulfate) found in the hexasaccharides prepared by testicular hyaluronidase digestion of shark cartilage chondroitin sulfate D. Glycobiology 7 (1997) 253-263
64. Pan T., Wong B.S., Liu T., Li R., Petersen R.B., and Sy M.S. Cell-surface prion protein interacts with glycosaminoglycans. Biochem. J. 368 (2002) 81-90
65. Papadas Th.A., Stylianou M., Mastronikolis N.S., Papageorgakopoulou N., Skandalis S., Goumas P., Theocharis D.A., and Vynios D.H. Alterations in the content and composition of glycosaminoglycans in human laryngeal carcinoma. Acta Otolaryngol. 122 (2002) 330-337
66. Papakonstantinou E., Dionyssopoulos A., Pesintzaki C., Minas A., and Karakiulakis G. Expression of proteoglycans and glycosaminoglycans in angiofibroma and fibrous plaque skin lesions from patients with tuberous sclerosis. Arch. Dermatol. Res. 295 (2003) 138-145
67. Pinto D.O., Ferreira P.L., Andrade L.R., Petrs-Silva H., Linden R., Abdelhay E., Araújo H.M.M., Alonso C.-E.V., and Pavão M.S.G. Biosynthesis and metabolism of sulfated glycosaminoglycans during Drosophila melanogaster development. Glycobiology 14 (2004) 529-536
68. Plaas A.H., West L.A., Thonar E.J., Karcioglu Z.A., Smith C.J., Klintworth G.K., and Hascall V.C. Altered fine structures of corneal and skeletal keratan sulfate and chondroitin/dermatan sulfate in macular corneal dystrophy. J. Biol. Chem. 276 (2001) 39788-39796
69. Rauch U. Extracellular matrix components associated with remodeling processes in brain. Cell. Mol. Life Sci. 61 (2004) 2031-2045
70. Rosen M., Edfors-Lilja I., and Bjornsson S. Quantitation of repetitive epitopes in glycosaminoglycans immobilized on hydrophobic membranes treated with cationic detergents. Anal. Biochem. 308 (2002) 210-222
71. Scapol L., Marchi E., and Viscomi G.C. Capillary electrophoresis of heparin and dermatan sulfate unsaturated disaccharides with triethylamine and acetonitrile as electrolyte additives. J. Chromatogr. A 735 (1996) 367-374
72. Schwartz N.B., and Domowicz M. Proteoglycans in brain development. Glycoconj. J. 21 (2004) 329-341
73. Sherman I.W., Eda S., and Winograd E. Cytoadherence and sequestration in Plasmodium falciparum: Defining the ties that bind. Microbes Infect. 5 (2003) 897-909
74. Skandalis S.S., Theocharis A.D., Theocharis D.A., Papadas Th.A., Vynios D.H., and Papageorgakopoulou N. Matrix proteoglycans are markedly affected in advanced laryngeal squamous cell carcinoma. Biochim. Biophys. Acta Mol. Basis Dis. 1689 (2004) 152-161
75. Stevens R.L., Colombo M., Gonzales J.J., Hollander W., and Schmid K. The glycosaminoglycans of the human artery and their changes in atherosclerosis. J. Clin. Invest. 58 (1976) 470-481
76. Sugahara K., Mikami T., Uyama T., Mizuguchi S., Nomura K., and Kitagawa H. Recent advances in the structural biology of chondroitin sulfate and dermatan sulfate. Curr. Opin. Struct. Biol. 13 (2003) 612-620
77. Theocharis A.D. Human colon adenocarcinoma is associated with specific post-translational modifications of versican and decorin. Biochim. Biophys. Acta 1588 (2002) 165-172
78. Theocharis A.D., and Theocharis D.A. High-performance capillary electrophoretic analysis of hyaluronan and galactosaminoglycan-disaccharides in gastrointestinal carcinomas. Differential disaccharide composition as a possible tool-indicator for malignancies. Biomed. Chromatogr. 16 (2002) 157-161
79. Theocharis A.D., Tsara M.E., Papageorgacopoulou N., Karavias D.D., and Theocharis D.A. Pancreatic carcinoma is characterized by elevated content of hyaluronan and chondroitin sulfate with altered disaccharide composition. Biochim. Biophys. Acta 1502 (2000) 201-206
80. Theocharis A.D., Tsara M.E., Papageorgakopoulou N., Vynios D.H., and Theocharis D.A. Characterization of glycosaminoglycans from human normal and scoliotic nasal cartilage with particular reference to dermatan sulphate. Biochim. Biophys. Acta 1528 (2001) 81-88
81. Theocharis A.D., Vynios D.H., Papageorgakopoulou N., Skandalis S.S., and Theocharis D.A. Altered content composition and structure of glycosaminoglycans and proteoglycans in gastric carcinoma. Int. J. Biochem. Cell Biol. 35 (2003) 376-390
82. Theocharis D.A., Papageorgakopoulou N., Vynios D.H., Anagnostides S., and Tsiganos C.P. Determination and structural characterization of dermatan sulfate in the presence of other galactosaminoglycans. J. Chromatogr. B 754 (2001) 297-309
83. Tsara M.E., Theocharis A.D., and Theocharis D.A. Compositional and structural alterations of proteoglycans in human rectum carcinoma with special reference to versican and decorin. Anticancer Res. 22 (2002) 2893-2898
84. Toyoki Y., Yoshihara S., Sasaki M., and Konn M. Characterization of glycosaminoglycans in regenerating canine liver. J. Hepatol. 26 (1997) 1135-1140
85. Tsuji A., Kinoshita T., and Hoshino M. Microdetermination of hexosamines. Chem. Pharm. Bull. 17 (1969) 1505-1510
86. Volpi N. Fractiontion of heparin, dermatan sulphate and chondroitin sulphate by sequential precipitation: A method to purify a single glycosaminoglycan species from a mixture. Anal. Biochem. 218 (1994) 382-391
87. Volpi N. Electrophoresis separation of glycosaminoglycans on notrocellulose membranes. Anal. Biochem. 240 (1996) 114-118
88. Volpi N. Disaccharide mapping of chondroitin sulphate of different origins by high performance capillary electrophoresis and high performance liquid chromatography. Carbohydr. Polymers 55 (2004) 273-281
89. Volpi N., and Maccari F. Detection of submicrogram quantities of glycoosaminoglycans on agarose gels by sequential staining with toluidine blue and stains-all. Electrophoresis 24 (2002) 4060-4066
90. Volpi N., and Maccari F. Microdetermination of chondroitin sulfate in normal human plasma by fluorophore-assisted carbohydrate electrophoresis (FACE). Clin. Chim. Acta 356 (2005) 125-133
91. Volpi N., Maccari F., and Titze J. Simultaneous detection of submicrogram quantities of hyaluronic acid and dermatan sulphate on agarose-gel by sequential staining with toluidine blue and stains-all. J. Chromatogr. B 820 (2005) 131-135
92. Vynios D.H. Microscale determinations using solid phase assays: Applications to biochemical, clinical and biotechnological sectors: A review. J. Liq. Chromatogr. RT 22 (1999) 2555-2574
93. Vynios D.H., Vamvacas S.S., Kalpaxis D.L., and Tsiganos C.P. Aggrecan immobilization onto polystyrene plates through electrostatic interactions with spermine. Anal. Biochem. 260 (1998) 64-70
94. Vynios D.H., Faraos A., Spyracopoulou G., Aletras A.J., and Tsiganos C.P. A solid-phase assay for quantitative analysis of sulfated glycosaminoglycans at the nanogram level: Application to tissue samples. J. Pharm. Biomed. Anal. 21 (1999) 859-865
95. Vynios D.H., Papadas Th.A., Faraos A., Mastronikolis N.S., Goumas P., and Tsiganos C.P. A solid phase assay for the determination of heparan sulfate and its application to normal and cancerous human cartilage samples. J. Immunoass. Immunochem. 22 (2001) 337-351
96. Vynios D.H., Karamanos N.K., and Tsiganos C.P. Advances in analysis of glycosaminoglygans: Its application for the assessment of physiological and pathological states of connective tissues. J. Chromatogr. B. 781 (2002) 21-38
97. Wadstrom T., and Ljungh A. Glycosaminoglycan-binding microbial proteins in tissue adhesion and invasion: Key events in microbial pathogenicity. J. Med. Microbiol. 48 (1999) 223-233
98. Worrall J.G., Wilkinson L.S., Bayliss M.T., and Edwards J.C. Zonal distribution of chondroitin-4-sulphate/dermatan sulphate and chondroitin-6-sulphate in normal and diseased human synovium. Ann. Rheum. Dis. 53 (1994) 35-38
99. Zamfir A., Seidler D.G., Schonherr E., Kresse H., and Peter-Katalinic J. On-line sheathless capillary electrophoresis/nanoelectrospray ionization-tandem mass spectrometry for the analysis of glycosaminoglycan oligosaccharides. Electrophoresis 25 (2004) 2010-2016