Lipid-modified insulin incorporated liposomes for selectively de

Details Lipid-modified insulin incorporated liposomes for selectively de Lipid-modified insulin incorporated liposomes for selectively de

1998-09-29

2000-12-12

Woodward, Michael P.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

424450, 530303, 536 6, 552201, 552202, A61K 3828, A61K 9127, C07K 1462

Patent

active

06159931&

ABSTRACT:
The present invention provides a lipid-modified insulin comprising an insulin molecule linked to an alkyl group by an amine linkage. Preferably, the alkyl group is a straight chain carbon comprising from about 14 to 20 carbon atoms. Preferably, the alkyl group is linked to the B1 phenylalanine or the B29 lysine. The present invention also provides a liposome comprising such lipid-modified insulin. Preferably, the liposomes are small unilamellar vesicles (SUVs) which have a particle size of less than 100 nm.
The present invention also provides a method for making a lipid-modified insulin. The method comprises reacting the protein with a hydrophobic aldehyde in the presence a reducing agent to provide a lipid-modified insulin in which an amino acid of the insulin is linked to an alkyl group by an amine linkage.
The present invention also relates to a method of killing hepatoma cells, particularly the hepatoma cells that are found in a hepatocellular carcinoma. The method comprises the steps of: providing liposomes containing a cytotoxic agent and having a lipid-modified insulin associated with the lipid bilayer thereof and exposing the hepatoma cells to the liposomes.

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patent: 5693609 (1997-12-01), Baker et al.
Young, Marie, "Incorporation of Insulin into a Liposomal Membrane" Master's Thesis, The Ohio State University, 1982.
Mei, Hong, "Formulation and Cell Uptake of Palmitoyl Insulin Incorporated Liposomal Phosphoramide Mustard" Master's Thesis, The Ohio State University, 1996.
"Stability Characterization and Hypoglycemic Effect of NB1-CIS-9-Hexadecenyl Insulin in Solution" by Mei, et al., Abstract on 1998 American Association of Pharmaceutical Scientists Annual Meeting in San Francisco.
"Lipid Modified Insulin: Site-Specific Synthesis, Separation, Characterization and Biological Activity" by Mei, et al., Pharmaceutical Research, 14(11):S156, 1997.
"Synthesis and Purification of NB1-Palmitoyl Insulin" by Tsai, et al., Journal of Pharmaceutical Sciences, vol. 86, No. 11, Nov. 1997, pp. 1264-1268.
"Formulation and Cell Uptake of Palmitoyl Insulin Incorporated Liposomal Phosphoramide Mustard" by Hong Mei, Master Thesis, The Ohio State University Graduate School, 1996.
"Incorporation of Insulin Into a Liposomal Membrane" by Regina Marie Young, Master Thesis, The Ohio State University , 1982.
"Palmitoyl Insulin as a Homing Ligand for Targeting Liposomes to Hepatocytes" by Yali J. Tsai, Dissertation, The University of Southern California, Aug. 1992.

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