Carbohydrate mediated drug delivery: Synthesis and characterization of new lipid-conjugates

Chemistry and Physics of Lipids

Volumn 186, Issue , 2015, Pages 30-38

  Ahmad, Moghis U ^a   Ali, Shoukath M ^a   Ahmad, Ateeq ^a   Sheikh, Saifuddin ^a   Chen, Paul ^b   Ahmad, Imran ^a  

^a Jina Pharmaceuticals Inc   (United States)

^b Nia Life Sciences Inc   (United States)

Author keywords

Drug delivery; Galactopyranoside; Lipid conjugate; Lipids; Mannopyranoside; Synthesis

Indexed keywords

4 (DIMETHYLAMINO BUTYLAMIDO) PHENYL ALPHA DEXTRO GALACTOPYRANOSIDE; 4 (DIMETHYLAMINO BUTYLAMIDO) PHENYL ALPHA DEXTRO MANNOPYRANOSIDE; CONCANAVALIN A; GLYCOCONJUGATE; GLYCOLIPID; LIPOSOME; MANNOSE BINDING PROTEIN; MANNOSE RECEPTOR; UNCLASSIFIED DRUG; BETA FRUCTOFURANOSIDASE; MANNOSE;

A549 CELL LINE; ARTICLE; CONTROLLED STUDY; HUMAN; HUMAN CELL; IN VITRO GENE TRANSFER; LIPOSOMAL DELIVERY; PRECIPITATION; REPORTER GENE; SYNTHESIS; CELL LINE; CHEMISTRY; DRUG DELIVERY SYSTEM; METABOLISM;

BETA-FRUCTOFURANOSIDASE; CELL LINE; CONCANAVALIN A; DRUG DELIVERY SYSTEMS; GLYCOLIPIDS; HUMANS; LIPOSOMES; MANNOSE;

EID: 84917741554     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2014.10.003     Document Type: Article

References (35)

1. I. Ahmad, A.K. Sarkar, and B.K. Bachhawat Design of liposomes to improve delivery of amphotericin B in the treatment of aspergillosis Mol. Cell. Biochem. 91 1989 85 90
2. I. Ahmad, A.S. Sarkar, and B.K. Bachhawat Mannosylated liposome-mediated delivery of amphotericin-B in the control of experimental aspergillosis in BALB/c mice J. Clin. Biochem. Nutr. 10 1991 171 179
3. M.U. Ahmad, S.M. Ali, A. Ahmad, S. Sheikh, and I. Ahmad Guggullipid derivatives: synthesis and applications Chem. Phys. Lipids 163 2010 362 366
4. S.M. Ali, A. Ahmad, S. Sheikh, M.U. Ahmad, R.C. Rane, P. Kale, M. Paithankar, D. Saptarishi, A. Sehgal, K. Maheshwari, and I. Ahmad Polyoxyl 60 hydrogenated castor oil free nanosomal formulation of immunosuppressant tacrolimus: pharmacokinetics, safety, and tolerability in rodents and humans Int. Immunopharmacol. 10 2010 325 330
5. J. Barjtburg, and J. Bolard Carrier effects on biological activity of amphotericin B Clin. Microbiol. Rev. 9 1996 512 531
6. R. Bellott, A. Auvrignon, T. Leblanc, Y. Perel, V. Gandemer, Y. Bertand, F. Mechinaud, P. Ballenger, J. Vernois, G. Leverger, A. Baruchel, and J. Robert Pharmacokinetics of liposomal daunorubicin (daunaXome) during a phase I-II study in children with relapsed acute lymphoblastic leukemia Cancer Chemother. Pharmacol. 47 2001 15 21
7. M. Cotton, and E. Wagner Non-viral approaches to gene therapy Curr. Opin. Biotechnol. 4 1993 705 710
8. R. Duncan, C.W. Seymour, L. Scarlett, J.B. Lloyd, P. Rejmanvoa, and J. Kopecek Fate of N-(2-hydroxypropyl) methacrylamide copolymers with pendent galactosamine residues after intravenous administration to rats Biochim. Biophys. Acta 880 1986 62 71
9. R.A. Dwek Glycobiology: toward understanding the functions of sugars Chem. Rev. 96 1996 683
10. Fumoto, S. Kawakami, Y. Ito, K. Shigeta, F. Yamashita, and M. Hashida Enhanced hepatocyte-selective in vivo gene expression by stabilized galactosylated liposome/plasmid DNA complex using sodium chloride for complex formation Mol. Ther. 10 2004 719 729
11. J. Gaucheron, C. Santaella, and P. Vierling In vitro gene transfer with a novel galactosylated spermine bolaamphiphile Bioconjug. Chem. 12 2001 569 575
12. M. Hashida, M. Nishikawa, F. Yamashita, and Y. Takakura Cell-specific delivery of genes with glycosylated carriers Adv. Drug Deliv. Rev. 52 2001 187 196
13. S.H. Hwang, K. Hayashi, K. Takayama, and Y. Maitani Liver-targeted gene transfer into a human hepatoblastoma cell line and in vivo sterylglucoside-containing cationic liposomes Gene Ther. 8 2001 1276 1280
14. M.J. Imber, S.V. Pizzo, W.J. Johnson, and D.O. Adams Selective diminution of the binding of mannose by murine macrophages in the late stages of activation J. Biol. Chem. 257 1982 5129 5135
15. S. Kawakami, F. Yamshita, M. Nishikawa, Y. Takakura, and M. Hashida Asialoglycoprotein receptor-mediated gene transfer using novel galactosylated cationic liposomes Biochim. Biophys. Res. Commun. 252 1998 78 83
16. S. Kawakami, A. Sato, M. Nishikawa, F. Yamashita, and M. Hashida Mannose receptor-mediated gene transfer into macrophages using novel mannosylated cationic liposomes Gene Ther. 7 2000 292 299
17. S. Kawakami, S. Fumoto, M. Nishikawa, F. Yamshita, and M. Hashida In vivo gene delivery to the liver using novel galactosylated cationic liposomes Pharm. Res. 17 2000 306 313
18. D.D. Lasic, and D. Papahadjopolos Liposomes revisited Science 217 1995 1245 1246
19. R.J. Linhardt, and T. Toida Carbohydrate in Drug Design Z.J. Witczak, K.A. Nieforth, 1997 Marcel Dekker New York
20. D.-Z. Liu, W.-Y. Chen, L.-M. Tsai, and S.-P. Yang Microcalorimetric and shear studies on the effects of cholesterol on the physical stability of lipid vesicles Colloids Surf. A 172 2000 57 67
21. C. Mangit, S. Kawakami, F. Yamashita, and M. Hashida Effect of galactose density on asialoglycoprotein receptor-mediated uptake of galactosylated liposomes J. Pharm. Sci. 94 2005 2266 2275
22. L.D. Mayer, R. Nayar, R.L. Thies, N.L. Boman, P.R. Cullis, and M.B. Bally Identification of vesicle properties that enhance the antitumor activity of liposomal vincristine against murine L1210 leukemia Cancer Chemother. Pharmacol. 33 1993 17 24
23. J.R. Morgan, M.B. Williams, and C.B. Howard Technetium-labelled liposome imaging for deep-seated infection Br. J. Radiol. 58 1985 35 39
24. J.C. Perales, T. Ferkol, M. Molas, and R.W. Hanson An evaluation of receptor-mediated gene transfer using synthetic DNA-ligand complexes Eur. J. Biochem. 226 1994 255 266
25. C. Plank, K. Zatlaoukal, M. Cotton, K. Mechtler, and E. Wagner Gene transfer into hepatocytes using asialoglycoprotein receptor mediated endocytosis of DNA complexed with an artificial tetra-antennary galactose ligand Bioconjug. Chem. 3 1992 533 539
26. R.C. Rathi, P. Kopeckova, B.A. Rihova, and J. Kopecek N-(2-hydroxypropyl) methacrylamide copolymers containing pendent saccharide moieties J. Polym. Sci. A: Polym. Chem. 29 1991 1895
27. P.H. Schlessinger, T.W. Doebber, B.F. Mandell, R. White, C. Deschryver, J.S. Rodman, M.J. Miller, and P.D. Stahl Plasma clearance of glycoproteins with terminal mannose and N-acetyl glucosamine by liver non parenchymal cells Biochem J. 176 1978 103 111
28. S. Sheikh, S.M. Ali, M.U. Ahmad, A. Ahmad, M. Mushtaq, M. Paithankar, J. Mandal, D. Saptarishi, A. Sehgal, K. Maheshwar, and I. Ahmad Nanosomal amphotericin B is an efficacious alternative to ambisome for fungal therapy Int. J. Pharm. 397 2010 103 108
29. K. Shigeta, S. Kawakami, Y. Higuchi, T. Okuda, H. Yagi, F. Yamashita, and M. Hashida Novel histidine-conjugated galactosylated cationic liposomes for efficient hepatocyte-selective gene transfer in human hepatoma HepG2 cells J. Control Release 118 2007 262 270
30. J. Sparano, U. Malik, L. Rajdev, C. Sarta, U. Hopkins, and A.C. Wolff Phase I trial of pegylated liposomal doxorubicin and docetaxel in advanced breast cancer J. Clin. Oncol. 19 2001 3117 3125
31. P.D. Stahl, J.S. Rodman, M.J. Miller, and P.H. Schlesinger Evidence for receptor mediated binding of glycoproteins, glycoconjugates and lysosomal glycosidases by alveolar macrophages Proc. Natl. Acad. Sci. 75 1978 1399 1403
32. X. Sun, L. Hai, Y. Wu, and Z.R. Zhang Targeted gene delivery to hepatoma cells using galactosylated liposome-polycation-DNA complexes (LPD) J. Drug Target. 13 2005 121 128
33. J. Vaage, E. Mayhew, D. Lasic, and F. Martin Therapy of primary and metastatic mouse mammary carcinomas with doxorubicin encapsulated in long circulating liposomes Int. J. Cancer 51 1992 942 948
34. A. Varki Biological roles of oligosaccharides: all of the theories are correct Glycobiology. 3 1993 97 130
35. G.Y. Wu, and C.H. Wu Receptor-mediated in vitro gene transformation by a soluble DNA carrier system J. Biol. Chem. 262 1987 4429 4432