Citation: Hua Nie, Yi Cheng, Pin-Jing Zheng, Li-Hua Luo, Sheng-Yuan Zhang. Lipase-catalyzed synthesis of novel galactosylated cholesterol[J]. Chinese Chemical Letters, ;2015, 26(5): 543-546. doi: 10.1016/j.cclet.2015.01.005 shu

Lipase-catalyzed synthesis of novel galactosylated cholesterol

1.
a College of Traditional Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China;
2.
b Medical College of Jiaying University, Meizhou 514031, China

Corresponding author: Yi Cheng,
Received Date: 31 January 2014
Available Online: 19 December 2014
Fund Project: This work was financially supported by the Ph.D. Programs FoundationofMinistry ofEducationofChina (No.20134425110010) (No.20134425110010)

In an organic phase system, an enzymes lipase was used as a catalyst to synthesize galactosylated cholesterol, (5-cholesten-3b-yl)[(4-O-β-D-galactopyranosyl)D-glucitol-6] sebacate (CHS-SE-LA), which contains galactose residues. Its chemical structure was characterized by ESI-MS, and NMR. For HepG2 cells, the cellular fluorescence intensities of liposomes modified with CHS-SE-LA (GAL-FL) were as much as 2.6-fold (p < 0.01) control liposomes (FL). Moreover, the presence of excess galactose significantly inhibited the uptake of GAL-FL suggesting ASGPR mediated uptake. In conclusion, the novel galactosylated ligand CHS-SE-LA was synthesized by lipase-catalyzation and revealed a great potential as drug carrier materials for hepatocyte-selective targeting.
- Cholesterol derivative,
- Liposomes,
- Asialoglycoprotein receptor,
- Lipase-catalyzed
1. [1]
  [1] A.N. Zelensky, J.E. Gready, The C-type lectin-like domain superfamily, FEBS J. 272 (2005) 6179-6217.
2. [2]
  [2] G.J. Bernardes, R. Kikkeri, M. Maglinao, et al., Design, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte- specific targeting, Org. Biomol. Chem. 8 (2010) 4987-4996.
3. [3]
  [3] S.L. Wang, F.B. Yu, T.Y. Jiang, et al., Design and synthesis of novel galactosylated polymers for liposomes as gene drug carriers targeting the hepatic asialoglycoprotein receptor, J. Drug Target. 16 (2008) 233-242.
4. [4]
  [4] M. Yamamoto, K. Ichinose, N. Ishii, et al., Utility of liposomes coated with polysaccharide bearing 1-amino-lactose as targeting chemotherapy for AH66 hepatoma cells, Oncol. Rep. 7 (2000) 107-111.
5. [5]
  [5] D.B. Rozema, D.L. Lewis, D.H. Wakefield, et al., Dynamic polyConjugates for targeted in vivo delivery of siRNA to hepatocytes, Proc. Natl. Acad. Sci. U. S. A. 104 (2007) 12982-12987.
6. [6]
  [6] Y. Miura, T. Ikeda, K. Kobayashi, Chemoenzymatically synthesized glycoconjugate polymers, Biomacromolecules 4 (2003) 410-415.
7. [7]
  [7] L.A. Sliedregt, P.C. Rensen, E.T. Rump, et al., Design and synthesis of novel amphiphilic dendritic galactosides for selective targeting of liposomes to the hepatic asialoglycoprotein receptor, J. Med. Chem. 42 (1999) 609-618.
8. [8]
  [8] S. Kawakami, J. Wong, A. Sato, et al., Biodistribution characteristics of mannosylated, fucosylated, and galactosylated liposomes in mice, Biochim. Biophys. Acta 1524 (2000) 258-265.
9. [9]
  [9] P.C. Rensen, L.A. Sliedregt, M. Ferns, et al., Determination of the upper size limit for uptake and processing of ligands by the asialoglycoprotein receptor on hepatocytes in vitro and in vivo, J. Biol. Chem. 276 (2001) 37577-37584.
10. [10]
  [10] S.N. Wang, Y.H. Deng, H. Xu, et al., Synthesis of a novel galactosylated lipid and its application to the hepatocyte-selective targeting of liposomal doxorubicin, Eur. J. Pharm. Biopharm. 62 (2006) 32-38.
11. [11]
  [11] N. Turan, J.F. Kennedy, in: Munishwar Nath Gupta (Ed.), Methods in Non-aqueous Enzymology, 47, Birkhäuser Verlag, Basel, 2002, , x + 218 pp., sFr. 228, Carbohydrate Polymers 47 (2002) 88.
12. [12]
  [12] E.A. Biessen, D.M. Beuting, H.C. Roelen, et al., Synthesis of cluster galactosides with high affinity for the hepatic asialoglycoprotein receptor, J. Med. Chem. 38 (1995) 1538-1546.
13. [13]
  [13] R.T. Lee, M.H. Wang, W.J. Lin, Y.C. Lee, New and more efficient multivalent glycoligands for asialoglycoprotein receptor of mammalian hepatocytes, Bioorg. Med. Chem. 19 (2011) 2494-2500.
14. [14]
  [14] S. Kawakami, F. Yamashita, M. Nishikawa, Y. Takakura, M. Hashida, Asialoglycoprotein receptor-mediated gene transfer using novel galactosylated cationic liposomes, Biochem. Biophys. Res. Commun. 252 (1998) 78-83.
15. [15]
  [15] C. Managit, S. Kawakami, F. Yamashita, M. Hashida, Effect of galactose density on asialoglycoprotein receptor-mediated uptake of galactosylated liposomes, J. Pharm. Sci. 94 (2005) 2266-2275.
16. [16]
  [16] S. Kawakami, C. Munakata, S. Fumoto, F. Yamashita, M. Hashida, Novel galactosylated liposomes for hepatocyte-selective targeting of lipophilic drugs, J. Pharm. Sci. 90 (2001) 105-113.
17. [17]
  [17] M. Wei, Y. Xu, Q. Zou, et al., Hepatocellular carcinoma targeting effect of PEGylated liposomes modified with lactoferrin, Eur. J. Pharm. Sci. 46 (2012) 131-141.
18. [18]
  [18] J. Chopineau, F.D. McCafferty, M. Therisod, A.M. Klibanov, Production of biosurfactants from sugar alcohols and vegetable oils catalyzed by lipases in a nonaqueous medium, Biotechnol. Bioeng. 31 (1988) 208-214.
19. [19]
  [19] A. Halldorsson, C.D. Magnusson, G.G. Haraldsson, Chemoenzymatic synthesis of structured triacylglycerols, Tetrahedron Lett. 42 (2001) 7675-7677.
20. [20]
  [20] F. Yu, T. Jiang, J. Zhang, L. Cheng, S. Wang, Galactosylated liposomes as oligodeoxynucleotides carrier for hepatocyte-selective targeting, Pharmazie 62 (2007) 528-533.
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沈阳化工大学材料科学与工程学院沈阳 110142