Sialic acid as a potential approach for the protection and targeting of nanocarriers

Expert Opinion on Drug Delivery

Volumn 8, Issue 7, 2011, Pages 921-937

  Bondioli, Lucia ^a   Ruozi, Barbara ^a   Belletti, Daniela ^a   Forni, Flavio ^a   Vandelli, Maria Angela ^a   Tosi, Giovanni ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

nanocarriers; sialic acid; stealth; targeting

Indexed keywords

GANGLIOSIDE GM1; NANOCARRIER; SIALIC ACID; SIALIC ACID DERIVATIVE;

CANCER DIAGNOSIS; CANCER INHIBITION; DRUG TARGETING; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LYMPHOCYTE ACTIVATION; NANOTECHNOLOGY; NONHUMAN; REVIEW; VIRUS DETECTION; VIRUS INFECTIVITY;

ANIMALS; DRUG CARRIERS; HUMANS; N-ACETYLNEURAMINIC ACID; NANOPARTICLES;

EID: 79959207466     PISSN: 17425247     EISSN: 17447593     Source Type: Journal    
DOI: 10.1517/17425247.2011.577061     Document Type: Review

References (74)

1. Bhattacharjee PS, Kumar S. An overview of novel drug delivery systems (NDDS). J Pharm Res 2009;2(2):155-7
2. Immordino ML, Dosio F, Cattel L. Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential. Int J Nanomed 2006;1(3):297-315
3. Huynh NT, Roger E, Lautram N, et al. The rise and rise of stealth nanocarriers for cancer therapy: passive versus active targeting. Nanomedicine (Lond) 2010;5(9):1415-33
4. Schauer R. Sialic acids and their role as biological masks. Trends Biochem Sci 1985;10(9):357-60 (Pubitemid 16220327)
5. Angata T, Varki A. Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective. Chem Rev 2002;102(2):439-69 (Pubitemid 35381636)
6. Kiefel MJ, Von Itzstein M. Recent advances in the synthesis of sialic acid derivatives and sialylmimetics as biological probes. Chem Rev 2002;102(2):471-90 (Pubitemid 35377622)
7. Hemeon I, Bennet AJ. Sialic acid and structural analogues: stereoselective syntheses. Synthesis 2007;13:1899-926 (Pubitemid 47074866)
8. Gabius HJ. Tumor lectinology: at the intersection of carbohy-drate chemistry, biochemistry, cell biology and oncology. Angew Chem Int Ed Eng 1988;27:1267-76
9. Schauer R. Sialic acids as regulators of molecular and cellular interactions. Curr Opin Struct Biol 2009;19(5):507-14
10. Perillo NL, Marcus ME, Baum LG. Galectins: versatile modulators of cell adhesion, cell proliferation and cell death. J Mol Med 1998;76:402-12 (Pubitemid 28218642)
11. Gabizon A, Papahadjopoulos D. Liposome formulations with prolonged circulation time in blood and enhanced uptake by tumors. Proc Natl Acad Sci USA 1988;85:6949-53
12. Kiss JZ, Rougon G. Cell biology of polysialic acid. Curr Opin Neurobiol 1997;7:640-6 (Pubitemid 27500823)
13. Yarema KJ, Bertozzi CR. Chemical approaches to glycobiology and emerging carbohydrate-based therapeutic agents. Curr Opin Chem Biol 1998;2(1):49-61 (Pubitemid 128419198)
14. Lanctot PM, Gage FH, Varki AP. The glycans of stem cells. Curr Opin Chem Biol 2007;11(4):373-80 (Pubitemid 47302845)
15. Gunawan J, Simard D, Gilbert M, et al. Structural and mechanistic analysis of sialic acid synthase NeuB from Neisseria meningitidis in complex with Mn2+, phosphoenolpyruvate, and N-acetylmannosaminitol. J Biol Chem 2005;280(5):3555-63 (Pubitemid 40223821)
16. Deszo EL, Steenbergen SM, Freedberg DI, et al. Escherichia coli K1 polysialic acid O-acetyltransferase gene, NeuO, and the mechanism of capsule form variation involving a mobile contingency locus. Proc Natl Acad Sci USA 2005;102(15):5564-9 (Pubitemid 40530297)
17. Weiss P, Ashwell G. Ligand-induced modulation of the hepatic receptor for asialoglycoproteins. Evidence for the role of cell surface hyposialylation. J Biol Chem 1989;264(20):11572-4 (Pubitemid 19185321)
18. Ourth DD, Bachinski LM. Bacterial sialic acid modulates activation of the alternative complement pathway of channel catfish. Dev Comp Immunol 1987;11(3):551-64
19. Saenko EL, Pipe SW. Strategies towards a longer acting factor VIII. Haemophilia 2006;12(3):42-51
20. Fredman P, Hedberg K, Brezicka T. Gangliosides as therapeutic targets for cancer. BioDrugs 2003;17(3):155-67 (Pubitemid 36693681)
21. Allen TM, Hansen C, Rutledge J. Liposomes with prolonged circulation time: factors affecting uptake by reticuloendothelial and other tissues. Biochim Biophys Acta 1989;981(1):27-35 (Pubitemid 19127766)
22. Kojima S, Sogawa Y, Tajiri Y, et al. Reduction and increase of the reticuloendothelial system (res) uptake of glycoprotein conjugated liposomes by linking a terminal sugar chain with sialic acid. Drug Deliv Syst 2002;17(1):63-8
23. Yamauchi H, Yano T, Kato T, et al. Effects of sialic acid derivative on long circulation time and tumor concentration of liposomes. Int J Pharm 1995;113:141-8 (Pubitemid 24344221)
24. Gregoriadis G, McCormack B, Wang Z, et al. Polysialic acids: potential in drug delivery. FEBS Lett 1993;315(3):271-6 (Pubitemid 23025022)
25. Fernandes AI, Gregoriadis G. Polysialyated asparaginase: preparation, activity and pharmacokinetics. Biochim Biophys Acta 1997;1341(1):26-34 (Pubitemid 27357031)
26. Fernandes AI, Gregoriadis G. The effect of polysialylation on the immunogenicity and antigenicity of asparaginase: implication in its pharmacokinetics. Int J Pharm 2001;217(1-2):215-24 (Pubitemid 32268647)
27. Jain S, Hreczuk-Hirst DH, McCormack B, et al. Polysialylated insulin: synthesis, characterization and biological activity in vivo. Biochim Biophys Acta 2003;1622(1):42-9 (Pubitemid 36776349)
28. Gregoriadis G, Jain S, Papaioannou I, et al. Improving the therapeutic efficacy of peptides and proteins: a role for polysialic acids. Int J Pharm 2005;300(1-2):125-30 (Pubitemid 41112174)
29. Allen TM, Chonn A. Large unilamellar liposomes with low uptake into the reticuloendothelial system. FEBS Lett 1987;223(1):42-6
30. Liu D, Mori A, Huang L. Large liposomes containing ganglioside GM1 accumulate effectively in spleen. Biochim Biophys Acta 1991;1066(2):159-65
31. Liu D, Mori A, Huang L. Role of liposome size and RES blockade in controlling biodistribution and tumor uptake of GM1-containing liposomes. Biochim Biophys Acta 1992;1104(1):95-101
32. Maruyama K, Okamoto A, Ishida AI, et al. Biodistribution and antitumor effect of adriamycin encapsulated in long-circulating liposomes containing amphipathic polyethylene glycol or ganglioside GM1. J Liposome Res 1994;4(1):701-23 (Pubitemid 24130566)
33. Yamauchi H, Kikuchi H, Yachi K, et al. Effects of glycophorin and ganglioside GM3 on the blood circulation and tissue distribution of liposomes in rats. Int J Pharm 1993;90(1):13-19
34. Nakabayashi S, Higashi K, Miyoshi S, et al. Sialic acid-containing glycolipid derivatives. US5243035; 1993
35. Pinnaduwage P, Huang L. The role of protein-linked oligosaccharide in the bilayer stabilization activity of glycophorin A for dioleoylphosphatidylethanolamine liposomes. Bioch Biophys Acta 1989;986(1):106-14 (Pubitemid 19281629)
36. Mora M, Sagrista ML, Trombetta D, et al. Design and characterization of liposomes containing long-chain N-acylpes for brain delivery: penetration of liposomes incorporating GM1 into the rat brain. Pharm Res 2002;19(10):1430-8 (Pubitemid 35266546)
37. Taira MC, Chiaramoni NS, Pecuch KM, et al. Stability of liposomal formulations in physiological conditions for oral drug delivery. Drug Deliv 2004;11(2):123-8 (Pubitemid 38437081)
38. Olivier JC, Vauthier C, Taverna M, et al. Stability of orosomucoid-coated polyisobutylcyanoacrylate nanoparticles in the presence of serum. J Control Release 1996;40(3):157-68 (Pubitemid 26238368)
39. Schmid K. Human plasma alpha 1-acid glycoprotein-biochemical properties, the amino acid sequence and the structure of the carbohydrate moiety, variants and polymorphism. Prog Clin Biol Res 1989;300:7-22
40. Spevak W, Nagy JO, Charych DH, et al. Polymerized liposomes containing c-glycosides of sialic acid: potent inhibitors of influenza virus in vitro infectivity. J Am Chem Soc 1993;115(3):1146-7 (Pubitemid 23090076)
41. Reichert A, Nagy JO, Spevak W, et al. Polydiacetylene liposomes functionalized with sialic acid bind and colorimetrically detect influenza virus. J Am Chem Soc 1995;117(2):829-30
42. Niikura K, Nagakawa K, Ohtake N, et al. Gold nanoparticle arrangement on viral particles through carbohydrate recognition: a non-cross-linking approach to optical virus detection. Bioconjug Chem 2009;20(10):1848-52
43. Chikae M, Fukuda T, Kerman K, et al. Amyloid-beta detection with saccharide immobilized gold nanoparticle on carbon electrode. Bioelectrochemistry 2008;74(1):118-23
44. Bondioli L, Costantino L, Ballestrazzi A, et al. PLGA nanoparticles surface decorated with the sialic acid, N-acetylneuraminic acid. Biomaterials 2010;31(12):3395-403
45. Owens DE, Peppas NA. Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles. Int J Pharm 2006;307(1):93-102 (Pubitemid 41773257)
46. Moghimi SM, Szebeni J. Stealthy liposomes and long circulating nanoparticles: critical issues in pharmacokinetics, opsonization and protein-binding properties. Prog Lipid Res 2003;42(6):463-78 (Pubitemid 37237636)
47. Tosi G, Vergoni AV, Ruozi B, et al. Sialic acid and glycopeptides conjugated PLGA nanoparticles for central nervous system targeting: in vivo pharmacological evidence and biodistribution. J Control Release 2010;145(1):49-57
48. Tosi G, Costantino L, Rivasi F, et al. Targeting the central nervous system: in vivo experiments with peptide-derivatized nanoparticles loaded with Loperamide and Rhodamine-123. J Control Release 2007;122(1):1-9 (Pubitemid 47284547)
49. Vergoni AV, Tosi G, Tacchi R, et al. Nanoparticles as drug delivery agents specific for CNS: in vivo biodistribution. Nanomed Nanotechnol Biol Med 2009;5(4):369-77
50. Tosi G, Fano RA, Badiali L, et al. Investigation on the mechanisms for Blood-Brain Barrier crossing of brain-targeted glycopeptides nanoparticles. Nanomedicine UK 2011;6(3):423-36
51. Lee JH, Jun YW, Yeon SI, et al. Dual-mode nanoparticle probes for high-performance magnetic resonance and fluorescence imaging of neuroblastoma. Angew Chem Int Ed Engl 2006;45(48):8160-2
52. Choi JS, Jun YW, Yeon SI, et al. Biocompatible heterostructured nanoparticles for multimodal biological detection. J Am Chem Soc 2006;128(50):15982-3
53. Xie HY, Xie M, Zhang ZL, et al. Wheat germ agglutinin-modified trifunctional nanospheres for cell recognition. Bioconjug Chem 2007;18(6):1749-55 (Pubitemid 350225481)
54. Sunamoto J, Noguchi T, Sato T, et al. Direct transfer of tumor surface antigenic protein (TSAP) from tumor cell to liposome for making liposomal vaccine. J Control Release 1992;20(2):143-54
55. Vodovozova EL, Moiseeva EV, Grechko GK, et al. Antitumour activity of cytotoxic liposomes equipped with selectin ligand SiaLeX, in a mouse mammary adenocarcinoma model. Eur J Cancer 2000;36:942-9 (Pubitemid 30214146)
56. Vodovozova L, Gaenko GP, Bobrikova ES, et al. A diglyceride derivative of methotrexate: synthesis and cytotoxic activity in addressed liposomes. Pharm Chem J 2008;41(6):10-14
57. Hiraia M, Minematsu H, Hiramatsu Y, et al. Novel and simple loading procedure of cisplatin into liposomes and targeting tumor endothelial cells. Int J Pharm 2010;391:274-83
58. Zheng JS, Zheng SJ, Zhang YB, et al. Sialic acid surface decoration enhances cellular uptake and apoptosis-inducing activity of selenium nanoparticles. Colloids Surf B Biointerfaces 2011;83:183-7
59. Chen WC, Completo GC, Sigal DS, et al. In vivo targeting of B-cell lymphoma with glycan ligands of CD22. Blood 2010;115(23):4778-86
60. Bevilacqua MP, Pober JS, Mendrick DL, et al. Identification of an inducible endothelial-leukocyte adhesion molecule. Proc Natl Acad Sci USA 1987;84:9238-42
61. Walz G, Aruffo A, Kolanus W, et al. Recognition by ELAM-1 of the sialyl-Lex determinant on myeloid and tumor cells. Science 1990;250(4984):1132-5 (Pubitemid 120031821)
62. Zeisiga R, Stahn R, Wenzel K, et al. Effect of sialyl Lewis X-glycoliposomes on the inhibition of E-selectin-mediated tumour cell adhesion in vitro. Biochim Biophys Acta 2004;1660:31-40 (Pubitemid 38125229)
63. Saiki I, Koike C, Obata A, et al. Functional role of sialyl lewis X and fibronectin-derived rgds peptide analogue on tumor-cell arrest in lungs followed by extravasation. Int J Cancer 1996;65:833-9 (Pubitemid 26127755)
64. Keil C, Zeisig R, Fichtner I. Effect of surface modified liposomes on the aggregation of platelets and tumor cells. Thromb Haemost 2005;94(2):404-11 (Pubitemid 41122496)
65. Hirai M, Minematsu H, Kondo N, et al. Accumulation of liposome with Sialyl Lewis X to inflammation and tumor region: application to in vivo bio-imaging. Biochem Biophys Res Comm 2007;353:553-8 (Pubitemid 46048704)
66. Zhang X, Teng Y, Fu Y, et al. Lectin-based biosensor strategy for electrochemical assay of glycan expression on living cancer cells. Anal Chem 2010;82:9455-60
67. Kato E, Akiyoshi K, Furuno T, et al. Interaction between ganglioside-containg liposomes and rat T-Lymphocyte: confocal fluorescence microscopic study. Biochem Biophys Res Comm 1994;203(3):1750-5 (Pubitemid 24321567)
68. Yanagihara K, Kato E, Hitomi S, et al. Activation of human T lymphocytes by ganglioside-containing liposomes. Glycoconj J 1999;16(1):59-65 (Pubitemid 29360911)
69. Kato E, Taguchi A, Sakashita SI, et al. Synthesis and function of sialic acid-conjugated cholesterols as ganglioside analogs: their reconstitution to liposomes and interaction with rat lymphocytes. Proc Japan Acad 2000;76(B):63-7
70. Rosen SD. Robert Feulgen Lecture 1993. L-selectin and its biological ligands. Histochemistry 1993;100(3):185-91 (Pubitemid 23285674)
71. DeFrees S, Phillips L, Guo L, et al. Sialyl lewis x liposomes as a multivalent ligand and inhibitor of e-selectin mediated cellular adhesion. J Am Chem Soc 1996;118(26):6101-4 (Pubitemid 26236843)
72. Murohara T, Margiotta J, Phillips JM, et al. Cardioprotection by liposome-conjugated sialyl Lewis(x)- oligosaccharide in myocardial and reperfusion injury. Cardiovasc Res 1995;30(6):965-74
73. Yamazaki N, Kojima S, Yokoyama H. Biomedical nanotechnology for active drug delivery systems by applying sugar-chain molecular functions. Curr Appl Phys 2005;5(2):112-17
74. Kingery-Wood JE, Williams KW, Sigal GB, et al. The agglutination of erythrocytes by influenza virus is strongly inhibited by liposomes incorporating an analog of sialyl gangliosides. J Am Chem Soc 1992;114(18):7303-5