RGD-xyloside conjugates prime glycosaminoglycans

Glycoconjugate Journal

Volumn 27, Issue 6, 2010, Pages 625-633

  Tran, Vy M ^a   Victor, Xylophone V ^b   Yockman, James W ^b   Kuberan, Balagurunathan ^a,b,c  

^a University of Utah   (United States)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF UTAH SCHOOL OF MEDICINE   (United States)

Author keywords

Biosynthesis; Cardiovascular; Chondroitin sulfate; Glycosaminoglycans; Heparan sulfate; Proteoglycans; RGD targeting; Tumor; Xylosides

Indexed keywords

AGLYCONE; ARGINYLGLYCYLASPARTIC ACID; GLYCOSAMINOGLYCAN; VITRONECTIN RECEPTOR; XYLOSE;

ANIMAL CELL; ANTICOAGULATION; ARTICLE; CANCER CELL; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CELL ACTIVATION; CELL TYPE; CHO CELL; CONTROLLED STUDY; DRUG STRUCTURE; ENDOTHELIUM CELL; FEMALE; HYDROPHOBICITY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; TARGET CELL;

ANIMALS; CATTLE; CELL LINE, TUMOR; CHO CELLS; CHROMATOGRAPHY, ION EXCHANGE; CRICETINAE; CRICETULUS; ENDOTHELIAL CELLS; GLYCOCONJUGATES; GLYCOSAMINOGLYCANS; GLYCOSIDES; HUMANS; OLIGOPEPTIDES;

EID: 77957558743     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-010-9306-1     Document Type: Article

References (45)

1. RD Cummings 2009 The repertoire of glycan determinants in the human glycome Mol. Biosyst. 5 1087 1104 1:CAS:528:DC%2BD1MXhtFarsb%2FN 10.1039/b907931a 19756298
2. PS Damus M Hicks RD Rosenberg 1973 Anticoagulant action of heparin Nature. 246 355 357 1:CAS:528:DyaE2cXkt1eguro%3D 10.1038/246355a0 4586320
3. J Hopwood M Hook A Linker U Lindahl 1976 Anticoagulant activity of heparin: isolation of antithrombin-binding sites FEBS Lett. 69 51 54 1:CAS:528:DyaE2sXjs1A%3D 10.1016/0014-5793(76)80651-5 992045
4. B Kuberan MZ Lech DL Beeler ZL Wu RD Rosenberg 2003 Enzymatic synthesis of antithrombin III-binding heparan sulfate pentasaccharide Nat. Biotechnol. 21 1343 1346 1:CAS:528:DC%2BD3sXosFOksLo%3D 10.1038/nbt885 14528313 (Pubitemid 37356620)
5. R Sasisekharan Z Shriver G Venkataraman U Narayanasami 2002 Roles of heparan-sulphate glycosaminoglycans in cancer Nat. Rev. Cancer. 2 521 528 1:CAS:528:DC%2BD38XkvFKltLY%3D 10.1038/nrc842 12094238
6. K Raman B Kuberan 2010 Chemical tumor biology of heparan sulfate proteoglycans Curr. Chem. Biol. 4 20 31 1:CAS:528:DC%2BC3cXisVKmtbo%3D 10.2174/187231310790226206 20596243
7. A Purushothaman L Chen Y Yang RD Sanderson 2008 Heparanase stimulation of protease expression implicates it as a master regulator of the aggressive tumor phenotype in myeloma J. Biol. Chem. 283 32628 32636 1:CAS:528: DC%2BD1cXhtlOjtLvM 10.1074/jbc.M806266200 18812315
8. L Fux N Ilan RD Sanderson I Vlodavsky 2009 Heparanase: busy at the cell surface Trends Biochem. Sci. 34 511 519 1:CAS:528:DC%2BD1MXhtFyqtbrE 10.1016/j.tibs.2009.06.005 19733083
9. I Vlodavsky N Ilan Y Nadir B Brenner BZ Katz A Naggi G Torri B Casu R Sasisekharan 2007 Heparanase, heparin and the coagulation system in cancer progression Thromb. Res. 120 Suppl. 2 S112 120 10.1016/S0049-3848(07)70139-1 18023704 (Pubitemid 350101779)
10. J Yang MA Price CL Neudauer C Wilson S Ferrone H Xia J Iida MA Simpson JB McCarthy 2004 Melanoma chondroitin sulfate proteoglycan enhances FAK and ERK activation by distinct mechanisms J. Cell Biol. 165 881 891 1:CAS:528: DC%2BD2cXltFKltbY%3D 10.1083/jcb.200403174 15210734 (Pubitemid 38821978)
11. GW Yip M Smollich M Gotte 2006 Therapeutic value of glycosaminoglycans in cancer Mol. Cancer Ther. 5 2139 2148 1:CAS:528:DC%2BD28Xps1ynsrY%3D 10.1158/1535-7163.MCT-06-0082 16985046 (Pubitemid 44530449)
12. NM Varki A Varki 2002 Heparin inhibition of selectin-mediated interactions during the hematogenous phase of carcinoma metastasis: rationale for clinical studies in humans Semin. Thromb. Hemost. 28 53 66 1:CAS:528:DC%2BD38XitlWlt7s%3D 10.1055/s-2002-20564 11885026 (Pubitemid 34194873)
13. L Borsig R Wong J Feramisco DR Nadeau NM Varki A Varki 2001 Heparin and cancer revisited: mechanistic connections involving platelets, P-selectin, carcinoma mucins, and tumor metastasis Proc. Natl. Acad. Sci. U. S. A. 98 3352 3357 1:CAS:528:DC%2BD3MXit1altrc%3D 10.1073/pnas.061615598 11248082 (Pubitemid 32220849)
14. TK Kishimoto K Viswanathan T Ganguly S Elankumaran S Smith K Pelzer JC Lansing N Sriranganathan G Zhao Z Galcheva-Gargova A Al-Hakim GS Bailey B Fraser S Roy T Rogers-Cotrone L Buhse M Whary J Fox M Nasr GJ Dal Pan Z Shriver RS Langer G Venkataraman KF Austen J Woodcock R Sasisekharan 2008 Contaminated heparin associated with adverse clinical events and activation of the contact system N. Engl. J. Med. 358 2457 2467 1:CAS:528:DC%2BD1cXmvFKmtb4%3D 10.1056/NEJMoa0803200 18434646 (Pubitemid 351793019)
15. DB Blossom AJ Kallen PR Patel A Elward L Robinson G Gao R Langer KM Perkins JL Jaeger KM Kurkjian M Jones SF Schillie N Shehab D Ketterer G Venkataraman TK Kishimoto Z Shriver AW McMahon KF Austen S Kozlowski A Srinivasan G Turabelidze CV Gould MJ Arduino R Sasisekharan 2008 Outbreak of adverse reactions associated with contaminated heparin N. Engl. J. Med. 359 2674 2684 1:CAS:528:DC%2BD1cXhsFaks7vL 10.1056/NEJMoa0806450 19052120
16. KD Gibson BJ Segen TK Audhya 1977 The effect of beta-D-xylosides on chondroitin sulphate biosynthesis in embryonic chicken cartilage in the absence of protein synthesis inhibitors Biochem. J. 162 217 233 1:CAS:528: DyaE2sXktlKit70%3D 849282
17. NB Schwartz PL Ho A Dorfman 1976 Effect of beta-xylosides on synthesis of cartilage-specific proteoglycan in chondrocyte cultures Biochem. Biophys. Res. Commun. 71 851 856 1:CAS:528:DyaE28XltF2qt7s%3D 10.1016/0006-291X(76)90909-8 134712
18. HC Robinson MJ Brett PJ Tralaggan DA Lowther M Okayama 1975 The effect of D-xylose, beta-D-xylosides and beta-D-galactosides on chondroitin sulphate biosynthesis in embryonic chicken cartilage Biochem. J. 148 25 34 1:CAS:528:DyaE2MXltV2itbc%3D 1156397
19. L Galligani J Hopwood NB Schwartz A Dorfman 1975 Stimulation of synthesis of free chondroitin sulfate chains by beta-D-xylosides in cultured cells J. Biol. Chem. 250 5400 5406 1:CAS:528:DyaE2MXkvFChu7k%3D 167013
20. NB Schwartz L Galligani PL Ho A Dorfman 1974 Stimulation of synthesis of free chondroitin sulfate chains by beta-D-xylosides in cultured cells Proc. Natl. Acad. Sci. U. S. A. 71 4047 4051 1:CAS:528:DyaE2MXmvVOrug%3D%3D 10.1073/pnas.71.10.4047 4372604
21. CO Abrahamsson U Ellervik J Eriksson-Bajtner M Jacobsson K Mani 2008 Xylosylated naphthoic acid-amino acid conjugates for investigation of glycosaminoglycan priming Carbohyd. Res. 343 1473 1477 1:CAS:528: DC%2BD1cXms1ynur4%3D 10.1016/j.carres.2008.04.006
22. M Okayama K Kimata S Suzuki 1973 The influence of p-nitrophenyl beta-d-xyloside on the synthesis of proteochondroitin sulfate by slices of embryonic chick cartilage J. Biochem. 74 1069 1073 1:CAS:528: DyaE2cXmslSitA%3D%3D 4770369
23. B Kuberan M Ethirajan XV Victor V Tran K Nguyen A Do 2008 "Click" xylosides initiate glycosaminoglycan biosynthesis in a mammalian cell line Chembiochem. 9 198 200 1:CAS:528:DC%2BD1cXlt1Whsrk%3D 10.1002/cbic.200700494 18085541 (Pubitemid 351196785)
24. TA Fritz FN Lugemwa AK Sarkar JD Esko 1994 Biosynthesis of heparan sulfate on beta-D-xylosides depends on aglycone structure J. Biol. Chem. 269 300 307 1:CAS:528:DyaK2cXntl2qug%3D%3D 8276811
25. XV Victor TK Nguyen M Ethirajan VM Tran KV Nguyen B Kuberan 2009 Investigating the elusive mechanism of glycosaminoglycan biosynthesis J. Biol. Chem. 284 25842 25853 1:CAS:528:DC%2BD1MXhtFWhtr%2FJ 10.1074/jbc.M109.043208 19628873
26. SJ DeNardo PA Burke BR Leigh RT O'Donnell LA Miers LA Kroger SL Goodman S Matzku A Jonczyk KR Lamborn GL DeNardo 2000 Neovascular targeting with cyclic RGD peptide (cRGDf-ACHA) to enhance delivery of radioimmunotherapy Cancer Biother. Radiopharm. 15 71 79 1:CAS:528:DC%2BD3cXhs1antLo%3D 10.1089/cbr.2000.15.71 10740655
27. A Meyer J Auernheimer A Modlinger H Kessler 2006 Targeting RGD recognizing integrins: drug development, biomaterial research, tumor imaging and targeting Curr. Pharm. Des. 12 2723 2747 1:CAS:528:DC%2BD28Xotlalsbk%3D 10.2174/138161206777947740 16918408 (Pubitemid 44184633)
28. K Park YS Kim GY Lee RW Park IS Kim SY Kim Y Byun 2008 Tumor endothelial cell targeted cyclic RGD-modified heparin derivative: inhibition of angiogenesis and tumor growth Pharm. Res. 25 2786 2798 1:CAS:528:DC%2BD1cXhsVeqsrfO 10.1007/s11095-008-9643-y 18581207
29. CB Carlson P Mowery RM Owen EC Dykhuizen LL Kiessling 2007 Selective tumor cell targeting using low-affinity, multivalent interactions ACS Chem. Biol. 2 119 127 1:CAS:528:DC%2BD2sXhtlKntbs%3D 10.1021/cb6003788 17291050 (Pubitemid 47490233)
30. RM Owen CB Carlson J Xu P Mowery E Fasella LL Kiessling 2007 Bifunctional ligands that target cells displaying the alpha v beta3 integrin Chembiochem. 8 68 82 1:CAS:528:DC%2BD2sXhtFCmsrs%3D 10.1002/cbic.200600339 17154219 (Pubitemid 46121574)
31. W Wang RT Borchardt B Wang 2000 Orally active peptidomimetic RGD analogs that are glycoprotein IIb/IIIa antagonists Curr. Med. Chem. 7 437 453 1:CAS:528:DC%2BD3cXhslOju7s%3D 10702618
32. Z Gyorgydeak L Szilagyi H Paulsen 1993 Synthesis, structure, and reactions of glycosyl azide J. Carbohyd. Chem. 12 139 163 1:CAS:528: DyaK3sXitlCgtr8%3D 10.1080/07328309308021266
33. β-glycosylated-L-asparagine derivatives. Synlett. 869-870 (1993)
34. U Aich D Loganathan 2005 Synthesis of N-(beta-glycopyranosyl) azidoacetamides J. Carbohyd. Chem. 24 1 12 1:CAS:528:DC%2BD2MXit1SktLc%3D 10.1081/CAR-200049402 (Pubitemid 41642743)
35. CW Tornoe C Christensen M Meldal 2002 Peptidotriazoles on solid phase: [1, 2, 3]-triazoles by regiospecific copper(i)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67 3057 3064 1:CAS:528:DC%2BD38XisVeks7w%3D 10.1021/jo011148j 11975567 (Pubitemid 34457265)
36. M Meldal CW Tornoe 2008 Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 108 2952 3015 1:CAS:528:DC%2BD1cXps1yhurk%3D 10.1021/cr0783479 18698735
37. CR Bertozzi LL Kiessling 2001 Chemical glycobiology Science. 291 2357 2364 1:CAS:528:DC%2BD3MXit1Kns7Y%3D 10.1126/science.1059820 11269316 (Pubitemid 32231790)
38. U Lindahl L Roden 1965 The role of galactose and xylose in the linkage of heparin to protein J. Biol. Chem. 240 2821 2826 1:CAS:528:DyaF2MXktFWgsL4%3D 14342301
39. K Sugahara 1989 The carbohydrate-protein linkage region of proteoglycans and glycosaminoglycan biosynthesis Seikagaku. 61 496 500 1:CAS:528: DyaL1MXltFWjt7c%3D 2794612
40. H Kitagawa M Oyama K Masayama Y Yamaguchi K Sugahara 1997 Structural variations in the glycosaminoglycan-protein linkage region of recombinant decorin expressed in Chinese hamster ovary cells Glycobiology. 7 1175 1180 1:CAS:528:DyaK1cXotVGm 10.1093/glycob/7.8.1175 9455918 (Pubitemid 28015806)
41. H Kitagawa Y Tone J Tamura KW Neumann T Ogawa S Oka T Kawasaki K Sugahara 1998 Molecular cloning and expression of glucuronyltransferase I involved in the biosynthesis of the glycosaminoglycan-protein linkage region of proteoglycans J. Biol. Chem. 273 6615 6618 1:CAS:528:DyaK1cXitVCqs7Y%3D 10.1074/jbc.273.12.6615 9506957 (Pubitemid 28160318)
42. S Gulberti V Lattard M Fondeur JC Jacquinet G Mulliert P Netter J Magdalou M Ouzzine S Fournel-Gigleux 2005 Phosphorylation and sulfation of oligosaccharide substrates critically influence the activity of human beta1, 4-galactosyltransferase 7 (GalT-I) and beta1, 3-glucuronosyltransferase I (GlcAT-I) involved in the biosynthesis of the glycosaminoglycan-protein linkage region of proteoglycans J. Biol. Chem. 280 1417 1425 1:CAS:528: DC%2BD2MXitFCksg%3D%3D 10.1074/jbc.M411552200 15522873
43. JD Esko TE Stewart WH Taylor 1985 Animal cell mutants defective in glycosaminoglycan biosynthesis Proc. Natl. Acad. Sci. U. S. A. 82 3197 3201 1:CAS:528:DyaL2MXktVChsb4%3D 10.1073/pnas.82.10.3197 3858816 (Pubitemid 15029573)
44. M Pfaff K Tangemann B Muller M Gurrath G Muller H Kessler R Timpl J Engel 1994 Selective recognition of cyclic RGD peptides of NMR defined conformation by alpha IIb beta 3, alpha V beta 3, and alpha 5 beta 1 integrins J. Biol. Chem. 269 20233 20238 1:CAS:528:DyaK2cXlsFWlt78%3D 8051114
45. D Kaufmann A Fiedler A Junger J Auernheimer H Kessler R Weberskirch 2008 Chemical conjugation of linear and cyclic RGD moieties to a recombinant elastin-mimetic polypeptide-a versatile approach towards bioactive protein hydrogels Macromol. Biosci. 8 577 588 1:CAS:528:DC%2BD1cXnslWlu7w%3D 10.1002/mabi.200700234 18350537