Top

Published in:

2017 | OriginalPaper | Chapter

Applications of Glycosaminoglycans in the Medical, Veterinary, Pharmaceutical, and Cosmetic Fields

Authors : José Kovensky, Eric Grand, María Laura Uhrig

Published in: Industrial Applications of Renewable Biomass Products

Publisher: Springer International Publishing

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

Glycosaminoglycans (GAGs) are complex polysaccharides ubiquitously present in the extracellular matrix of mammalian tissues, where they constitute the gelatinous material responsible for maintaining the cells together, in an intimate association with a variety of proteins. Although their structures are not strictly regular, they are composed of a repeating unit of a hexosamine-containing disaccharide. Most of them possess uronic acid residues, and with the exception of hyaluronic acid, they also carry sulfate groups. As a consequence of their high negative charge, they have an extraordinary capacity to absorb water. GAGs participate in many relevant biological processes by interaction with a plethora of proteins, and thus, a large number of applications in different fields have been conceived for GAGs and their derivatives.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Wirtschaft"

Online-Abonnement

Mit Springer Professional "Wirtschaft" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 340 Zeitschriften

aus folgenden Fachgebieten:

Bauwesen + Immobilien
Business IT + Informatik
Finance + Banking
Management + Führung
Marketing + Vertrieb
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

previous chapter Innovative Systems from Clickable Biopolymer-Based Hydrogels for Drug Delivery

next chapter Bacterial Cellulose Nanoribbons: A New Bioengineering Additive for Biomedical and Food Applications

Afratis NA, Gialeli C, Nikitovic D, Tsegenidis T, Karousou E, Theocharis AD, Pavao MS, Tzanakakis GN, Karamanos NK (2012) Glycosaminoglycans: key players in cancer cell biology and treatment. FEBS J 279:1177–1197CrossRef

Afratis NA, Karamanos NK, Piperigkou Z, Vynios DH, Theocharis AD (2016) The role of heparins and nano-heparins as therapeutic tool in breast cancer. Glycoconj J. 2016. doi:10.1007/s10719-016-9742-7

Ahmad S, Ansari AA (2011) Therapeutic roles of heparin anticoagulants in cancer and related disorders. Med Chem 7:504–517CrossRef

Aimi T, Suzuki K, Hoshino T, Mizushima T (2015) Dextran sulfate sodium inhibits amyloid-β oligomer binding to cellular prion protein. J Neurochem 134:611–617CrossRef

Aquino SA, Park PW (2010) Diverse functions of glycosaminoglycans in infectious diseases. Prog Mol Biol Transl Sci 93:373–394CrossRef

Aquino SA, Park PW (2016) Glycosaminoglycans and infection. Front Biosci (Landmark Ed) 21:1260–1277CrossRef

Arevalo MT, Simpson-Haidaris PJ, Jin X, Chen H, Quinn MH (2011) Compositions and methods for inhibition of or treatment of dengue virus infection. PCT Int Appl WO 2011153458

Axelsson J, Xu D, Kang BN, Nussbacher JK, Handel TM, Ley K, Sriramarao P, Esko JD (2012) Inactivation of heparan sulfate 2-O-sulfotransferase accentuates neutrophil infiltration during acute inflammation in mice. Blood 120:1742–1751CrossRef

Bachar G, Cohen K, Hod R, Feinmesser R, Mizrachi A, Shpitzer T, Katz O, Peer D (2011) Hyaluronan-grafted particle clusters loaded with mitomycin C as selective nanovectors for primary head and neck cancers. Biomaterials 32:4840–4848CrossRef

Badylak SF (1997) Biomaterial derived from vertebrate liver tissue. US Patent 6,379,710

Badylak SF, Demeter RJ, Hiles M, Voytik SL, Knapp PM Jr (1994) Fluidized intestinal submucosa and its use as an injectable tissue graft. US Patent 5,275,826 A

Badylak SF, Voytik SL, Brightman A, Waninger M (1995) Urinary bladder submucosa derived tissue graft. US Patent 5,554,389

Badylak SF, Voytik-Harbin SL, Brightman AO, Tullius RS (1997) Stomach submucosa derived tissue graft. US Patent 6,099,567

Barrowcliffe TJ (2012) History of heparin. Handb Exp Pharmacol 207:3–22CrossRef

Basappa, Rangappa KS, Sugahara K (2014) Roles of glycosaminoglycans and glycanmimetics in tumor progression and metastasis. Glycoconj J 31:461–467CrossRef

Beasley KL, Weiss M, Weiss RA (2009) Hyaluronic acid fillers: a comprehensive review. Facial Plast Surg 25:86–94CrossRef

Bedini E, Parrilli M (2012) Synthetic and semi-synthetic chondroitin sulfate oligosaccharides, polysaccharides, and glycomimetics. Carbohydr Res 356:75–85CrossRef

Belting M (2014) Glycosaminoglycans in cancer treatment. Thromb Res 133:S95–S101CrossRef

Benitez A, Yates TJ, Lopez LE, Cerwinka WH, Bakkar A, Lokeshwar VB (2011) Targeting hyaluronidase for cancer therapy: antitumor activity of sulfated hyaluronic acid in prostate cancer cells. Cancer Res 71:4085–4095CrossRef

Bernstein EF, Underhill CB, Hahn PJ, Brown DB, Uitto J (1996) Chronic sun exposure alters both the content and distribution of dermal glycosaminoglycans. Br J Dermatol 135:255–262CrossRef

Boeriu CG, Springer J, Kooy FK, van den Broek LAM, Eggink G (2013) Production methods for hyaluronan. Int J Carbohydr Chem. Article ID 624967 2013:14CrossRef

Bonafe F, Govoni M, Giordano E, Caldarera C, Guarnieri C, Muscari C (2014) Hyaluronan and cardiac regeneration. J Biomed Sci 21:100. 13 ppCrossRef

Borsig L, Vlodavsky I, Ishai-Michaeli R, Torri G, Vismara E (2011) Sulfated hexasaccharides attenuate metastasis by inhibition of P-selectin and heparanase. Neoplasia 13:445–452CrossRef

Bottegoni C, Muzzarelli RAA, Giovannini F, Busilacchi A, Gigante A (2014) Oral chondroprotection with nutraceuticals made of chondroitin sulphate plus glucosamine sulphate in osteoarthritis. Carbohydr Polym 109:126–138CrossRef

Brougham CM, Levingstone TJ, Jockenhoevel S, Flanagan TC, O’Brien FJ (2015) Incorporation of fibrin into a collagen–glycosaminoglycan matrix results in a scaffold with improved mechanical properties and enhanced capacity to resist cell-mediated contraction. Acta Biomater 26:205–214CrossRef

Cagno V, Donalisio M, Civra A, Volante M, Veccelli E, Oreste P, Rusnati M, Lembo D (2014) Highly sulfated K5 Escherichia coli polysaccharide derivatives inhibit respiratory syncytial virus infectivity in cell lines and human tracheal-bronchial histocultures. Antimicrob Agents Chemother 58:4782–4794CrossRef

Campion C, Pini APJ, Gogoi RN, Gilthorpe J (2012) Sulfated oligosaccharides for use in treatment of neurodegenerative diseases. PCT Int Appl WO 2012/160337

Capila I, Linhardt RJ (2002) Heparin-protein interactions. Angew Chem Int Ed Eng 41:390–412CrossRef

Cayre Y, Allouche R (2017) Produit pour lutter contre la prolifération des cellules cancéreuse. Fr Demande FR 3039065

Chang P-h (2014) Pharmaceutical formulation containing glycosaminoglycan. PCT Int Appl WO 2014142938, PCT Int Appl WO 2014143085

Cheng G, Cao B (2015) Zwitterionic polysaccharide polymers having antifouling, antimicrobial and optical transparency properties. PCT Int Appl WO 2015057645 A1

Conrad HE (ed) (1998) Heparin-binding proteins. Academic, San Diego

Coombe DR, Kett WC (2005) Heparan sulfate-protein interactions: therapeutic potential through structure-function insights. Cell Mol Life Sci 62:410–424CrossRef

Coppa GV, Facinelli B, Magi G, Marini E, Zampini L, Mantovani V, Galeazzi T, Padella L, Marchesiello RL, Santoro L, Coscia A, Peila C, Volpi N, Gabrielli O (2016) Human milk glycosaminoglycans inhibit in vitro the adhesion of Escherichia coli and Salmonella fyris to human intestinal cells. Pediatr Res 79:603–607CrossRef

Cordo Russo RI, García MG, Alaniz L, Blanco G, Alvarez E, Hajos SE (2008) Hyaluronan oligosaccharides sensitize lymphoma resistant cell lines to vincristine by modulating P-glycoprotein activity and PI3K/Akt pathway. Int J Cancer 122:1012–1018CrossRef

Crepaldi G, Fellin R, Calabrò A, Rossi A, Ventura A, Mannarino E, Senin U, Ciuffetti G, Descovich GC, Gaddi A, Rimondi S, Pozza G, Vicari A, Carandente O, Mancini M, Rubba P, Postiglione A, Strano A, Avellone G, Davì G, Novo S, Pinto A, Capurso A, Resta F, Mogavero AM, Bucci A, Antonini R, Lalloni L (1990) Double-blind multicenter trial on a new medium molecular weight glycosaminoglycan current therapeutic effects and perspectives for clinical use. Atherosclerosis 81:233–243CrossRef

Cruz L, Meyers C (2013) Differential dependence on host cell glycosaminoglycans for infection of epithelial cells by high-risk HPV types. PLoS One 8:e68379CrossRef

Da Costa Dias B, Jovanovic K, Gonsalves D, Weiss SFT (2011) Structural and mechanistic commonalities of amyloid-β and the prion protein. Prion 5:126–137CrossRef

Davis DAS, Parish CR (2013) Heparan sulfate: a ubiquitous glycosaminoglycan with multiple roles in immunity. Front Immunol 4:470. 7 pp

De Vita D, Giordano S (2012) Effectiveness of intravesical hyaluronic acid/chondroitin sulfate in recurrent bacterial cystitis: a randomized study. Int Urogynecol J 23:1707–1713CrossRef

DeAngelis PL, Lane RS (2016) Heparosan/therapeutic prodrug complexes and methods of making and using same. WO 2016/065309

DeAngelis PL, Liu J, Linhardt RJ (2013) Chemoenzymatic synthesis of glycosaminoglycans: re-creating, re-modeling and re-designing nature’s longest or most complex carbohydrate chains. Glycobiology 23:764–777CrossRef

Della Valle F, Romeo A (1989) Esters of hyaluronic acid. US Patent 4,851,521

Dicker KT, Gurski LA, Pradhan-Bhatt S, Witt RL, Farach-Carson MC, Jia X (2014) Hyaluronan: a simple polysaccharide with diverse biological functions. Acta Biomater 10:1558–1570CrossRef

Eklund E, Ekman-Ordeberg G, Malmstrom A (2013) Treatment of cytokine mediated conditions. Can Pat Appl CA 2779838

Esko JD (2001) Special considerations for proteoglycans and glycosaminoglycans and their purification. Curr Protoc Mol Biol 17:17.2.1–17.2.9

Fabricius H-A (2015) Sulfated polysaccharides for use in the treatment of cancer. PCT Int Appl WO 2015/059177

Finelli I, Chiessi E, Galesso D, Renier D, Paradossi G (2009) Gel-like structure of a hexadecyl derivative of hyaluronic acid for the treatment of osteoarthritis. Macromol Biosci 9:646–653CrossRef

Fitton H, Gardiner V (2011) Anti-viral formulations. PCT Int Appl WO 2011/100805

Flores Salgado F, Benitez Jimenez AF, Costa Rierola M, Flores Costa R, Flores Costa L (2013) Partially depolymerized glycosaminoglycan silver and gold salts. PCT Int Appl WO 2013/121001

Freudenberg U, Zieris A, Chwalek K, Tsurkan MV, Maitz MF, Atallah P, Levental KR, Eming SA, Werner C (2015) Heparin desulfation modulates VEGF release and angiogenesis in diabetic wounds. J Control Release 220(Part A):79–88CrossRef

Fu L, Suflita M, Linhardt RJ (2016) Bioengineered heparins and heparan sulfates. Adv Drug Deliv Rev 97:237–249CrossRef

Fukuda T, Matsumoto E, Miura Y (2015) Interaction between multimeric sulfated saccharides and Alzheimer amyloid β (1-42). Chem Lett 44:1482–1484CrossRef

Funderburgh JL (2000) Keratan sulfate: structure, biosynthesis, and function. Glycobiology 10:951–958CrossRef

Fux L, Ilan N, Sanderson RD, Vlodavsky I (2009) Heparanase: busy at the cell surface. Trends Biochem Sci 34:511–519CrossRef

Galus A, Mallet J-M, Lembo D, Cagno V, Djabourov M, Lortat-Jacob H, Bouchemal K (2016) Hexagonal-shaped chondroitin sulfate self-assemblies have exalted anti-HSV-2 activity. Carbohydr Polym 136:113–120CrossRef

García B, Merayo-Lloves J, Martin C, Alcalde I, Quirós LM, Vazquez F (2016) Surface proteoglycans as mediators in bacterial pathogens infections. Front Microbiol 7:220. 11 pp

Genco T, Zemljič LF, Bračič M, Stana-Kleinschek K, Heinze T (2012) Physicochemical properties and bioactivity of a novel class of cellulosics: 6-deoxy-6-amino cellulose sulfate. Macromol Chem Phys 213:539–548CrossRef

Gilbert TW, Sellaro TL, Badylak SF (2006) Decellularization of tissues and organs. Biomaterials 27:3675–3683

Gomes AM, Stelling MP, Pavão MSG (2013, 2013) Heparan sulfate and heparanase as modulators of breast cancer progression. BioMed Res Int:852093. 11 pp

Gomes AM, Kozlowski EO, Borsig L, Teixeira FCOB, Vlodavsky I, Pavão MSG (2015) Antitumor properties of a new non-anticoagulant heparin analog from the mollusk Nodipecten nodosus: effect on P-selectin, heparanase, metastasis and cellular recruitment. Glycobiology 25:386–393CrossRef

Gray E, Hogwood J, Mulloy B (2012) The anticoagulant and antithrombotic mechanisms of heparin. Handb Exp Pharmacol 207:43–61CrossRef

Grohmann S, Hildebrand G, Liefeith K (2014) Active substance-loaded biocompatible polyelectrolyte multilayers based on sulfated glycosaminoglycans, methods for producing the multilayers, and use of the multilayers. PCT Int Appl WO 2014/147080; Ger Offen DE 102013204742

Harenberg J (1998) Review of pharmacodynamics, pharmacokinetics, and therapeutic properties of sulodexide. Med Res Rev 18:1–20CrossRef

Hendricks GL, Velazquez L, Pham S, Qaisar N, Delaney JC, Viswanathan K, Albers L, Comolli JC, Shriver Z, Knipe DM, Kurt-Jones EA, Fygenson DK, Trevejo JM, Wang JP, Finberg RW (2015) Heparin octasaccharide decoy liposomes inhibit replication of multiple viruses. Antivir Res 116:34–44CrossRef

Herrero LJ, Foo S-S, Sheng K-C, Chen W, Forwood MR, Bucala R, Mahalingam S (2015) Pentosan polysulfate: a novel glycosaminoglycan-like molecule for the effective treatment of alphavirus-induced cartilage destruction and inflammatory disease. J Virol 89:8063–8076CrossRef

Herrero-Mendez A, Palomares T, Castro B, Herrero J, Granado MH, Bejar JM, Alonso-Varona A (2015) HR007: a family of biomaterials based on glycosaminoglycans for tissue repair. J Tissue Eng Regen Med. doi:10.1002/term.1998

Hidari KI, Abe T, Suzuki T (2013) Carbohydrate-related inhibitors of dengue virus entry. Viruses 5:605–618CrossRef

Hoshiba T, Chen G, Endo C, Maruyama H, Wakui M, Nemoto E, Kawazoe N, Tanaka M (2016) Decellularized extracellular matrix as an in vitro model to study the comprehensive roles of the ECM in stem cell differentiation. Stem Cells Int. Article ID 6397820, 10 pp

Huang Y, Yao X, Zhang R, Ouyang L, Jiang R, Liu X, Song C, Zhang G, Fan Q, Wang L, Huang W (2014) Cationic conjugated polymer/fluoresceinamine-hyaluronan complex for sensitive fluorescence detection of CD44 and tumor-targeted cell imaging. ACS Appl Mater Interfaces 6:19144–19153CrossRef

Jia X, Kiick KL (2009) Hybrid multicomponent hydrogels for tissue engineering. Macromol Biosci 9:140–156CrossRef

Jinno-Oue A, Tanaka A, Shimizu N, Mori T, Sugiura N, Kimata K, Isomura H, Hoshino H (2013) Inhibitory effect of chondroitin sulfate type E on the binding step of human T-cell leukemia virus type 1. AIDS Res Hum Retrovir 29:621–629CrossRef

Kallestrup E, Jørgensen S, Nordling J, Hald T (2005) Treatment of interstitial cystitis with Cystistat®, a hyaluronic acid product. Scand J Urol Nephrol 39:143–147CrossRef

Kavasi RM, Berdiaki A, Spyridaki I, Corsini E, Tsatsakis A, Tzanakakis G, Nikitovic D (2017) HA metabolism in skin homeostasis and inflammatory disease. Food Chem Toxicol 101:128–138CrossRef

Keane TJ, Swinehart IT, Badylak SF (2015) Methods of tissue decellularization used for preparation of biologic scaffolds and in vivo relevance. Methods 84:25–34CrossRef

Khaderi K (2014) Compositions and methods for treating injuries to the visual system of a human. US Patent 0,212,404 A1

Khanlari A, Detamore MS, Gehrke SH (2013) Increasing cross-linking efficiency of methacrylated chondroitin sulfate hydrogels by copolymerization with oligo(ethylene glycol) diacrylates. Macromolecules 46:9609–9617CrossRef

Khanlari A, Suekama TC, Gehrke SH (2015a) Structurally versatile glycosaminoglycan hydrogels for biomedical applications. Macromol Symp 358:67–77CrossRef

Khanlari A, Suekama TC, Detamore MS, Gehrke SH (2015b) Structurally diverse and readily tunable photocrosslinked chondroitin sulfate based copolymers. J Polym Sci Part B Polym Phys 53:1070–1079CrossRef

Khanlari A, Schulteis JE, Suekama TC, Detamore MS, Gehrke SH (2015c) Designing crosslinked hyaluronic acid hydrogels with tunable mechanical properties for biomedical applications. J Appl Polym Sci 132. doi:10.1002/APP.42009

Kim E, Okumura M, Sawa H, Miyazaki T, Fujikura D, Yamada S, Sugahara K, Sasaki M, Kimura T (2011) Paradoxical effects of chondroitin sulfate-E on Japanese encephalitis viral infection. Biochem Biophys Res Commun 409:717–722

Kim S-H, Turnbull J, Guimond SJ (2011) Extracellular matrix and cell signalling: the dynamic cooperation of integrin, proteoglycan and growth factor receptor. Endocrinology 209:139–151

Kirn-Safran CB, D’Souza SS, Carson DD (2008) Heparan sulfate proteoglycans and their binding proteins in embryo implantation and placentation. Semin Cell Dev Biol 19:187–193CrossRef

Kobayashi F, Yamada S, Taguwa S, Kataoka C, Naito S, Hama Y, Tani H, Matsuura Y, Sugahara K (2012) Specific interaction of the envelope glycoproteins E1 and E2 with liver heparan sulfate involved in the tissue tropismatic infection by hepatitis C virus. Glycoconj J 29:211–220CrossRef

Kozlowski EO, Pavao MSG (2011) Effect of sulfated glycosaminoglycans on tumor invasion and metastasis. Front Biosci Sch Ed S3:1541–1551CrossRef

Kozlowski EO, Pavao MSG, Borsig L (2011) Ascidian dermatan sulfates attenuate metastasis, inflammation and thrombosis by inhibition of P-selectin. J Thromb Haemost 9:1807–1815CrossRef

Krichen F, Volpi N, Sila A, Maccari F, Mantovani V, Galeotti F, Ellouz-Chaabouni S, Bougatef A (2017) Purification, structural characterization and antiproliferative properties of chondroitin sulfate/dermatan sulfate from tunisian fish skins. Int J Biol Macromol 95:32–39CrossRef

Kroma A, Feliczak-Guzik A, Nowak I (2012) The use of glycosaminoglycans in cosmetic products. Chemik 66:136–139

Kwok JCF, Warren P, Fawcett JW (2012) Chondroitin sulfate: a key molecule in the brain matrix. Int J Biochem Cell Biol 44:582–586CrossRef

Ladet S (2013) Multilayer implants for delivery of therapeutic agents. PCT Int Appl WO 2013046057

Lee EC, Davis-Poynter N, Nguyen CTH, Peters AA, Monteith GR, Strounina E, Popat A, Ross BP (2016) GAG mimetic functionalised solid and mesoporous silica nanoparticles as viral entry inhibitors of herpes simplex type 1 and type 2 viruses. Nanoscale 8:16192–16196CrossRef

Lee-Sayer SSM, Dong Y, Arif AA, Olsson M, Brown KL, Johnson P (2015) The where, when, how, and why of hyaluronan binding by immune cells. Front Immunol 6:150CrossRef

Ley K, Cerrito M, Arfors KE (1991) Sulfated polysaccharides inhibit leukocyte rolling in rabbit mesentery venules. Am J Phys 260:1667–1673

Li Y, Liu Y, Xia W, Lei D, Voorhees JJ, Fisher GJ (2013) Age-dependent alterations of decorin glycosaminoglycans in human skin. Sci Rep 3:2422. 8 ppCrossRef

Lian W, Wu M, Huang N, Gao N, Xiao C, Li Z, Zhang Z, Zheng Y, Peng W, Zhao J (2013) Anti-HIV-1 activity and structure-activity-relationship study of a fucosylated glycosaminoglycan from an echinoderm by targeting the conserved CD4 induced epitope. Biochim Biophys Acta 1830:4681–4691CrossRef

Liang Y, Kiick KL (2014) Heparin-functionalized polymeric biomaterials in tissue engineering and drug delivery applications. Acta Biomater 10:1588–1600CrossRef

Liaw PC, Becker DL, Stafford AR, Fredenburgh JC, Weitz JI (2001) Molecular basis for the susceptibility of fibrin-bound thrombin to inactivation by heparin cofactor II in the presence of dermatan sulfate but not heparin. J Biol Chem 276:20959–20965CrossRef

Lin H-Y (2015) Compound of glycosaminoglycan, preparation method and use thereof. PCT Int Appl WO 2015/028172 A1; US Patent Appl Publ US 20150065446

Liu L, Liu Y, Li J, Du G, Chen J (2011) Microbial production of hyaluronic acid: current state, challenges, and perspectives. Microb Cell Factories 10:99–108CrossRef

Liu C-C, Zhao N, Kanekiyo T, Yamaguchi Y, Cirrito JR, Holtzman DM, Bu G (2016) Neuronal heparan sulfates promote amyloid pathology by modulating brain amyloid-β clearance and aggregation in Alzheimer’s disease. Sci Transl Med 8:332ra44CrossRef

Lompardía SL, Díaz M, Papademetrio DL, Mascaró M, Pibuel M, Álvarez E, Hajos SE (2016) Hyaluronan oligomers sensitize chronic myeloid leukemia cell lines to the effect of Imatinib. Glycobiology 26:343–352CrossRef

Lundin A, Bergström T, Andrighetti-Fröhner CR, Bendrioua L, Ferro V, Trybala E (2012) Potent anti-respiratory syncytial virus activity of a cholestanol-sulfated tetrasaccharide conjugate. Antivir Res 93:101–109CrossRef

Manveen K, Sethi MK, Zaia J (2017) Extracellular matrix proteomics in schizophrenia and Alzheimer’s disease. Anal Bioanal Chem 409:379–394CrossRef

Marchi E, Tamagnone G (1994) Method of treatment of diabetic nephropathy by means of sulodexide of medicines containing it. US Patent 5,496,807

Martín R, Martín C, Escobedo S, Suárez JE, Quirós LM (2013) Surface glycosaminoglycans mediate adherence between HeLa cells and lactobacillus salivarius Lv72. BMC Microbiol 13:210. 11 ppCrossRef

Martinez P, Vergoten G, Colomb F, Bobowski M, Steenackers A, Carpentier M, Allain F, Delannoy P, Julien S (2013) Over-sulfated glycosaminoglycans are alternative selectin ligands: insights into molecular interactions and possible role in breast cancer metastasis. Clin Exp Metastasis 30:919–931CrossRef

Matheny RG (2015) Compositions and methods for preventing cardiac arrhythmia. US Patent 2015/0164959 A1

Mathieu C, Dhondt KP, Chalons M, Mely S, Raoul H, Negre D, Cosset F-L, Gerlier D, Vives RR, Horvat B (2015) Heparan sulfate-dependent enhancement of henipavirus infection. MBio 6:1–10CrossRef

Memi E, Karakiulakis G, Goma F, Papakonstantinou E (2012) The functional role of glycosaminoglycans in the pathophysiology of the thyroid gland and their putative role as prognostic, diagnostic and therapeutic agents in thyroid pathologies. Rev Clin Pharmacol Pharmacokinet Int Ed 26:61–86

Mikami T, Kitagawa H (2013) Biosynthesis and function of chondroitin sulfate. Biochim Biophys Acta Gen Subj 1830:4719–4733CrossRef

Misra S, Hascall VC, Markwald RR, Ghatak S (2015) Interactions between hyaluronan and its receptors (CD44, RHAMM) regulate the activities of inflammation and cancer. Front Immunol 6:201. 31 ppCrossRef

Mizumoto S, Sugahara (2013) Glycosaminoglycans are functional ligands for receptor for advanced glycation end-products in tumors. FEBS J 280:2462–2470CrossRef

Mizumoto S, Takahashi J, Sugahara K (2012) Receptor for advanced glycation end products (RAGE) functions as receptor for specific sulfated glycosaminoglycans, and anti-RAGE antibody or sulfated glycosaminoglycans delivered in vivo inhibit pulmonary metastasis of tumor cells. J Biol Chem 287:18985–18994CrossRef

Monfort J, Pelletier J-P, Garcia-Giralt N, Martel-Pelletier J (2008) Biochemical basis of the effect of chondroitin sulphate on osteoarthritis articular tissues. Ann Rheum Dis 67:735–740CrossRef

Mousa SA (2015) Composition and method for sulfated non-anticoagulant low molecular weight heparins in cancer and tumor metastasis. US Patent Appl Publ US 20150132399

Mousa SA (2016) Composition and method of use for combinations of anti-viral protease, polymerase inhibitors and natural bioactive compounds in the treatment of hepatitis C infection. US Patent Appl Publ US20160346308 A1

Murphy CM, Duffy GP, Schindeler A, O’Brien FJ (2016) Effect of collagen-glycosaminoglycan scaffold pore size on matrix mineralization and cellular behavior in different cell types. J Biomed Mater Res Part A 104:291–304CrossRef

Nakano T, Betti M, Pietrasik Z (2010) Extraction, isolation and analysis of chondroitin sulfate glycosaminoglycans. Recent Pat Food Nutr Agric 2:61–74CrossRef

Nickel JC, Egerdie RB, Steinhoff G, Palmer B, Hanno P (2010) A multicenter, randomized, double-blind, parallel group pilot evaluation of the efficacy and safety of intravesical sodium chondroitin sulfate versus vehicle control in patients with interstitial cystitis/painful bladder syndrome. Urology 76:804–809CrossRef

Nikitovic D, Chatzinikolaou G, Tsiaoussis J, Tsatsakis A, Karamanos NK, Tzanakakis GN (2012) Insights into targeting colon cancer cell fate at the level of proteoglycans/glycosaminoglycans. Curr Med Chem 19:4247–4258CrossRef

Nishimura Y, Shudo H, Seto H, Hoshino Y, Miura Y (2013) Syntheses of sulfated glycopolymers and analyses of their BACE-1 inhibitory activity. Bioorg Med Chem Lett 23:6390–6395CrossRef

Nugent MA (2000) Heparin sequencing brings structure to the function of complex oligosaccharides. Proc Natl Acad Sci U S A 97:10301–10303CrossRef

O'Hearn A, Wang M, Cheng H, Lear-Rooney CM, Koning K, Rumschlag-Booms E, Varhegyi E, Olinger G, Rong L (2015) Role of EXT1 and glycosaminoglycans in the early stage of filovirus entry. J Virol 89:5441–5449CrossRef

Papakonstantinou E, Roth M, Karakiulakis G (2012) Hyaluronic acid: a key molecule in skin aging. Dermato-Endocrinol 4:253–258CrossRef

Papy-Garcia D, Christophe M, Huynh MB, Sineriz F, Sissoeff L, Sepulveda-Diaz JE, Raisman-Vozari R (2011) Glycosaminoglycans, protein aggregation and neurodegeneration. Curr Protein Pept Sci 12:258–268CrossRef

Papy-Garcia D, Huynh MB, Soussi-Yanicostas N, Vozari R, Sineriz F, Yanicostas C (2013) Method of diagnosis, prognosis, or treatment of neurodegenerative diseases. PCT Int Appl WO 2013/053954.

Paul TJ, Kelly H, Zuchniarz J, Ahmed T, Prabhakar R (2016) Design of heparin oligosaccharide based molecules for inhibition of Alzheimer amyloid beta (Aβ40) aggregation. Can J Chem 94:1090–1098CrossRef

Peer D (2015) Liposomal formulations for delivery of nucleic acids. Int Appl WO 2015/198326

Persson A, Tykesson E, Westergren-Thorsson G, Malmström A, Ellervik U, Mani K (2016) Xyloside-primed chondroitin sulfate/dermatan sulfate from breast carcinoma cells with a defined disaccharide composition has cytotoxic effects in vitro. J Biol Chem 291:14871–14882CrossRef

Petrey AC, de la Motte CA (2014) Hyaluronan, a crucial regulator of inflammation. Front Immunol 5:101CrossRef

Pisano C, Vlodavsky I, Ilan N, Zunino F (2014) The potential of heparanase as a therapeutic target in cancer. Biochem Pharmacol 89:12–19CrossRef

Pomin VH (2015a) A dilemma in the glycosaminoglycan-based therapy: synthetic or naturally unique molecules? Med Res Rev 35:1195–1219CrossRef

Pomin VH (2015b) Sulfated glycans in inflammation. Eur J Med Chem 92:353–369CrossRef

Pomin VH, Mulloy B (2015) Current structural biology of the heparin interactome. Curr Opin Struct Biol 34:17–25CrossRef

Prestwich GD, Kennedy TP (2011) Methods for treating or preventing the spread of cancer using semi-synthetic glycosaminoglycosan ethers. PCT Int Appl WO 2011/094149

Prestwich GD, Oottamasathein S, Kennedy T (2011) Applications of partially and fully sulfated hyaluronan. PCT Int Appl WO 2011/156445

Prestwich GD, Oottamasathien S, Kennedy TP (2013) Applications of partially and fully sulfated hyaluronan. US Patent Appl 0,209,531

Puperi DS, O’Connell RW, Punske ZE, Wu Y, West JL, Grande-Allen KJ (2016) Hyaluronan hydrogels for a biomimetic spongiosa layer of tissue engineered heart valve scaffolds. Biomacromolecules 17:1766–1775CrossRef

Pye DA, Ogundipe OD (2016) Pharmaceutical extracts and uses thereof. PCT Int Appl WO 2016/067008

Qian W, Tao L, Wang Y, Zhang F, Li M, Huang S, Wang A, Chen W, Yue Z, Chen L, Liu Y, Huang C, Zhang L, Li Y, Lu Y (2015) Downregulation of integrins in cancer cells and anti-platelet properties are involved in holothurian glycosaminoglycan-mediated disruption of the interaction of cancer cells and platelets in hematogenous metastasis. J Vasc Res 52:197–209CrossRef

Radhakrishnan K, Tripathy J, Datey A, Chakravortty D, Raichur AM (2015) Mesoporous silica-chondroitin sulphate hybrid nanoparticles for targeted and bio-responsive drug delivery. New J Chem 39:1754–1760CrossRef

Rankin KS, Frankel D (2016) Hyaluronan in cancer – from the naked mole rat to nanoparticle therapy. Soft Matter 12:3841–3848CrossRef

Rawat M, Hsieh-Wilson L (2014) Glycosaminoglycan mimetics. US Patent 8,912,149 B1

Reinmueller J, Dirting K (2012) Antiinfective composition. PCT Int Appl WO 2012/168462; Ger Offen DE 102011077393

Ren X, Weisgerber DW, Bischoff D, Lewis MS, Reid RR, He T-C, Yamaguchi DT, Miller TA, Harley BAC, Lee JC (2016) Nanoparticulate mineralized collagen scaffolds and BMP-9 induce a long-term bone cartilage construct in human mesenchymal stem cells. Adv Healthc Mater 5:1821–1830CrossRef

Rilla K, Tiihonen R, Kultti A, Tammi M, Tammi R (2008) Pericellular hyaluronan coat visualized in live cells with a fluorescent probe is scaffolded by plasma membrane protrusions. J Histochem Cytochem 56:901–910CrossRef

Ritchie JP, Ramani VC, Ren Y, Naggi A, Torri G, Casu B, Penco S, Pisano C, Carminati P, Tortoreto M, Zunino F, Vlodavsky I, Sanderson RD, Yang Y (2011) SST0001, a chemically modified heparin, inhibits myeloma growth and angiogenesis via disruption of the heparanase/syndecan-1 axis. Clin Cancer Res 17:1382–1393CrossRef

Ronca F, Palmieri L, Panicucci P, Ronca G (1998) Anti-inflammatory activity of chondroitin sulfate. Osteoarthr Cartil 6(Suppl A):14–21CrossRef

Said JS, Trybala E, Görander S, Ekblad M, Liljeqvist J-A, Jennische E, Lange S, Bergström T (2016) The cholestanol-conjugated sulfated oligosaccharide PG545 disrupts the lipid envelope of herpes simplex virus particles. Antimicrob Agents Chemother 60:1049–1057CrossRef

Sakiyama-Elbert SE (2014) Incorporation of heparin into biomaterials. Acta Biomater 10:1581–1587CrossRef

Salbach J, Rachner TD, Rauner M, Hempel U, Anderegg U, Franz S, Simon J-C, Hofbauer LC (2012) Regenerative potential of glycosaminoglycans for skin and bone. J Mol Med 90:625–635CrossRef

Savage JR, Pulsipher A, Rao NV, Kennedy TP, Prestwich GD, Ryan ME, Lee WY (2016) A modified glycosaminoglycan, GM-0111, inhibits molecular signaling involved in periodontitis. PLoS One 11:e0157310/1

Sayari N, Balti R, Ben Mansour M, Ben Amor I, Graiet I, Gargouri J, Bougatef A (2016) Anticoagulant properties and cytotoxic effect against HCT116 human colon cell line of sulfated glycosaminoglycans isolated from the Norway lobster (Nephrops norvegicus) shell. Biomed Pharmacother 80:322–330CrossRef

Schaefer L, Schaefer RM (2010) Proteoglycans: from structural compounds to signaling molecules. Cell Tissue Res 339:237–246CrossRef

Schnabelrauch M, Scharnweber D, Schiller J (2013) Sulfated glycosaminoglycans as promising artificial extracellular matrix components to improve the regeneration of tissues. J Curr Med Chem 20:2501–2523CrossRef

Schwoerer R, Zubkova OV, Turnbull JE, Tyler PC (2013) Synthesis of a targeted library of heparan sulfate hexa- to dodecasaccharides as inhibitors of β-secretase: potential therapeutics for Alzheimer’s disease. Chem Eur J 19:6817–6823

Scott IR (1988) Skin treatment composition. EP 0295092 B1

Seki Y, Mizukura M, Ichimiya T, Suda Y, Nishihara S, Masuda M, Takase-Yoden S (2012) O-sulfate groups of heparin are critical for inhibition of ecotropic murine leukemia virus infection by heparin. Virology 424:56–66CrossRef

Silva LA, Khomandiak S, Ashbrook AW, Weller R, Heise MT, Morrison TE, Dermody TS (2014) A single-amino-acid polymorphism in chikungunya virus E2 glycoprotein influences glycosaminoglycan utilization. J Virol 88:2385–2397CrossRef

Simionescu D, Mercuri JJ (2016). Shape-memory sponge hydrogel biomaterial. US Patent 9,283,301

Spero M, Weiss MS, Kopp JB (2005) Methods using glycosaminoglycans for the treatment of kidney disease. PCT Int Appl WO 2006039709 A1

Staples GO, Zaia J (2011) Mass spectrometry in carbohydrate sequencing and binding analysis. In: Wang B, Boons G-J (eds) Carbohydrate recognition: biological problems, methods, and applications. Wiley, Hoboken, pp 257–300CrossRef

Stern R, Maibach HI (2008) Hyaluronan in skin: aspects of aging and its pharmacologic modulation. Clin Dermatol 26:106–122CrossRef

Stewart KL, Hughes E, Yates EA, Akien GR, Huang T-Y, Lima MA, Rudd TR, Guerrini M, Hung S-C, Radford SE, Middleton DA (2016) Atomic details of the interactions of glycosaminoglycans with amyloid β fibrils. J Am Chem Soc 138:8328–8331CrossRef

Ströh LJ, Stehle T (2014) Glycan engagement by viruses: receptor switches and specificity. Ann Rev Virol 1:285–306CrossRef

Tangso KJ, da Cunha PHCD, Spicer P, Li J, Boyd BJ (2016) Antimicrobial activity from colistin-heparin lamellar-phase complexes for the coating of biomedical devices. ACS Appl Mater Interfaces 8:31321–31329CrossRef

Theocharis AD, Skandalis SS, Gialeli C, Karamanos NK (2016) Extracellular matrix structure. Adv Drug Deliv Rev 97:4–27CrossRef

Turley E (2010) Topically administered, skin-penetrating glycosaminoglycan formulations suitable for use in cosmetic and pharmaceutical applications. CA 2703532 A1; PCT Int Appl WO 2011/140630 A1

Tyler PC, Guimond SE, Turnbull JE, Zubkova OV (2015) Single-entity heparan sulfate glycomimetic clusters for therapeutic applications. Angew Chem Int Ed 54:2718–2723CrossRef

Verges Milano J, Garcia Garcia A, Ruhi Roura R, Montell Bonaventura E, Garcia Lopez M, Alaez Verson CR, Escaich Ferrer J, Egea Maiquez J, Lorrio Gonzalez S, Negredo Madrigal P (2011) Sulphated disaccharides for the treatment of neurodegenerative and/or neurovascular diseases. PCT Int. Appl. WO 2011/080203

Vistoli G, De Maddis D, Cipak A, Zarkovic N, Carini M, Aldini G (2013) Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): an overview of their mechanisms of formation. Free Radic Res 47:3–27CrossRef

Volpi N, Schiller J, Stern R, Soltes L (2009) Role, metabolism, chemical modifications and applications of hyaluronan. Curr Med Chem 16:1718–1745CrossRef

Von Recum HA, Hijaz A (2014) Glycosaminoglycans for chemokine drug delivery. U.S. Pat. Appl. Publ. US 20140364360

Vuillermoz B, Wegrowski Y, Contet-Audonneau J-L, Danoux L, Pauly G, Maquart F-X (2005) Influence of aging on glycosaminoglycans and small leucine-rich proteoglycans production by skin fibroblasts. Mol Cell Biochem 277:63–72CrossRef

Wang P, Ding K (2014) Proteoglycans and glycosaminoglycans in misfolded proteins formation in Alzheimer’s disease. Protein Pept Lett 21:1048–1056CrossRef

Weigel PH, Fuller GM, LeBoeuf RD (1986) A model for the role of hyaluronic acid and fibrin in the early events during the inflammatory response and wound healing. J Theor Biol 119:219–234CrossRef

Wu RL, Huang L, Zhao H-C, Geng X-P (2017) Hyaluronic acid in digestive cancers. J Cancer Res Clin Oncol 143:1–16CrossRef

Xiao L, Tong Z, Chen Y, Pochan DJ, Sabanayagam CR, Jia X (2013) Hyaluronic acid-based hydrogels containing covalently integrated drug depots: implication for controlling inflammation in mechanically stressed tissues. Biomacromolecules 14:3808–3819CrossRef

Xu D, Olson J, Cole JN, van Wijk XM, Brinkmann V, Zychlinsky A, Nizet V, Esko JD, Chang Y-C (2015) Heparan sulfate modulates neutrophil and endothelial function in antibacterial innate immunity. Infect Immun 83:3648–3656CrossRef

Yang R-M, Fu C-P, Li N-N, Wang L, Xu X-D, Yang D-Y, Fang J-Z, Jiang X-Q, Zhang L-M (2014) Glycosaminoglycan-targeted iron oxide nanoparticles for magnetic resonance imaging of liver carcinoma. Mater Sci Eng C Mater Biol Appl 45:556–563CrossRef

Yang X, Du H, Liu J, Zhai G (2015) Advanced nanocarriers based on heparin and its derivatives for cancer management. Biomacromolecules 16:423–436CrossRef

Yip GW, Smollich M, Götte M (2006) Therapeutic value of glycosaminoglycans in cancer. Mol Cancer Ther 5:2139–2148CrossRef

Yue Z, Wang A, Zhu Z, Tao L, Li Y, Zhou L, Chen W, Lu Y (2015) Holothurian glycosaminoglycan inhibits metastasis via inhibition of P-selectin in B16F10 melanoma cells. Mol Cell Biochem 410:143–154CrossRef

Yuk SH, Oh KS, Cho SH, Lee BS, Kim SY, Kwak BK, Kim K, Kwon IC (2011) Glycol chitosan/heparin immobilized iron oxide nanoparticles with a tumor-targeting characteristic for magnetic resonance imaging. Biomacromolecules 12:2335–2343CrossRef

Zhang Q, Li J, Liu C, Song C, Li P, Yin F, Xiao Y, Jiang W, Zong A, Zhang X, Wang F (2015) Protective effects of low molecular weight chondroitin sulfate on amyloid beta (Aβ)-induced damage in vitro and in vivo. Neuroscience 305:169–182CrossRef

Zhang RR, Strebe JK, Kuo JS (2016) Heparan sulfates promote amyloid pathology in Alzheimer disease. Neurosurgery 79:N12–N13

Zhang X, Zhao X, Lang Y, Li Q, Liu X, Cai C, Hao J, Li G, Yu G (2016) Low anticoagulant heparin oligosaccharides as inhibitors of BACE-1, the Alzheimer’s β-secretase. Carbohydr Polym 151:51–59

Zhao W, McCallum SA, Xiao Z, Zhang F, Linhardt RJ (2012) Binding affinities of vascular endothelial growth factor (VEGF) for heparin-derived oligosaccharides. Biosci Rep 32:71–81CrossRef

Zheng S, Jin Z, Han J, Cho S, Nguyen VD, Young Ko S, Park J-O, Park S (2016) Preparation of HIFU-triggered tumor-targeted hyaluronic acid micelles for controlled drug release and enhanced cellular uptake. Colloids Surf B: Biointerfaces 143:27–36CrossRef

Zhong WP, Chin HG, Lee EJ, Guo S, Yip GW, Lam Y (2015) Divergent synthesis of chondroitin sulfate disaccharides and identification of sulfate motifs that inhibit triple negative breast cancer. Sci Rep 5:14355. 8 ppCrossRef

Zhou X, Jin L (2016) The structure-activity relationship of glycosaminoglycans and their analogues with β-amyloid peptide. Protein Pept Lett 23:358–364CrossRef

Zhou H, Roy S, Cochran E, Zouaoui R, Chu CL, Duffner J, Zhao G, Smith S, Galcheva-Gargova Z, Karlgren J, Dussault N, Kwan RY, Moy E, Barnes M, Long A, Honan C, Qi YW, Shriver Z, Ganguly T, Schultes B, Venkataraman G, Kishimoto TK (2011) M402, a novel heparan sulfate mimetic, targets multiple pathways implicated in tumor progression and metastasis. PLoS One 6:e21106CrossRef

Zhu M, Feng Q, Sun Y, Li G, Bian L (2016) Effect of cartilaginous matrix components on the chondrogenesis and hypertrophy of mesenchymal stem cells in hyaluronic acid hydrogels. J Biomed Mater Res Part B Appl Biomater. doi:10.1002/jbm.b.33760

Zieris A, Dockhorn R, Röhrich A, Zimmermann R, Müller M, Welzel PB, Tsurkan MV, Sommer J-U, Freudenberg U, Werner C (2014) Biohybrid networks of selectively desulfated glycosaminoglycans for tunable growth factor delivery. Biomacromolecules 55:4439–4446CrossRef

Zimmer R, Courty J (2012) Compositions comprising multivalent synthetic ligands of surface nucleolin and glycosaminoglycans. PCT Int Appl WO 2012/045750

Title: Applications of Glycosaminoglycans in the Medical, Veterinary, Pharmaceutical, and Cosmetic Fields
Authors: José Kovensky
Eric Grand
María Laura Uhrig
Publisher: Springer International Publishing
Book: Industrial Applications of Renewable Biomass Products
Print ISBN: 978-3-319-61287-4

Electronic ISBN: 978-3-319-61288-1

Copyright Year: 2017
DOI: https://doi.org/10.1007/978-3-319-61288-1_5

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Springer Professional "Wirtschaft"

Premium Partners