Method and compositions for lipidization of hydrophilic molecule

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Tripeptides – e.g. – tripeptide thyroliberin – etc.

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530307, 530317, 546294, C07K 5062, C07K 5083, C07K 512, C07D21371

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059070307

ABSTRACT:
Fatty acid derivatives of sulfhydryl-containing compounds (for example, sulfhydryl-containing peptides or proteins) comprising fatty acid-conjugated products with a disulfide linkage are employed for delivery of the compounds to mammalian cells. This modification markedly increases the absorption of the compounds by mammalian cells relative to the rate of absorption of the unconjugated compounds, as well as prolonging blood and tissue retention of the compounds. Moreover, the disulfide linkage in the conjugate is quite labile in the cells and thus facilitates intracellular release of the intact compounds from the fatty acid moieties.

REFERENCES:
patent: 5599903 (1997-02-01), Kauvar et al.
patent: 5629020 (1997-05-01), Leone-Bay et al.
patent: 5635380 (1997-06-01), Naftilan et al.
patent: 5679643 (1997-10-01), Kauvar et al.
patent: 5763570 (1998-06-01), Kauvar et al.
Ubuka, T. et al., "Synthesis of disulfides related to glutathione and their detection in tissue," Chem. Abstracts 106:728, Abstract No. 156843v (1987).
Chemical Abstracts, vol. 102(2),abst. 12733d Jan. 14, 1985.
Chemical Abstracts, vol. 107(20),abst.No. 183,493h Nov. 16, 1987.
Chemical Abstracts, vol. 114 (22),abst.No. 214,316d Jun. 3, 1991.
Chu, et al., Chem. Abstr., 121(21):212, Abstract No. 246582y (1994).
Ekrami, H. M., et al., FEBS Letters, 371(3):283-286 (1995).
Ekrami, H. M. , et al., Chem. Abstr., 124(3):1042, Abstract No. 3036q (1996).
Huang, et al., Molec. Immunol., 31(15):1191-1199 (1994).
Yodoya, E., et al., J. Pharm. and Experimental Therapeutics, 271(3):1509-1513 (1994).
Chu, et al., "High-Potency Hybrid Compounds Related to Insulin and Amphioxs Insulin-like Peptide", Biochem., 33(4):10387-13092 (1994).
Ekrami, H.M., "Positively-Charged and Lipophilic Bowman-Birk Protease Inhibitor Conjugates: Synthesis and Characterization of the Pharmaceutical and Chemopreventive Properties," A Dissertation, UMI Dissertation Services, Ann Arbor, MI, Chapter II, pp. 98-226 (after Jan. 25, 1995).
Letsinger, R. et al. (1989) Proc. Natl. Acad. Sci. USA 86, 6553-6556.
Kabanov, A. et al. (1989) Protein Eng. 3, 39-42.
Hashimoto, M. et al., Pharm. Res. 6, 171-176 (1989).
Martins, M.B.F. et al., Biochimie 72, 671-675 (1990).
Muranishi, S. et al., Pharm. Res. 8,649-652 (1991).
Hughes, Richard A. et al. (1992) J. Pharm. Sci., vol. 81, No. 8, 845-848.
Hughes, Richard A. et al. (1991) J. Pharm. Sci., vol. 80, No. 12, 1103-1105.
Toth, Istvan (1994) J. Drug Targeting, vol. 2, 217-239.
Chekhonin, V.P. et al (1991) FEBS, vol. 287, 149-152.
Lee, V.H.L. (1988) CRC. Critical Rev. Ther. Drug Delivery Sys. 5, 69-97.
Artursson, P., and Magnusson, C. (1990) J. Pharm. Sci. 79, 595-600.
Gonzalez-Mariscal, L.M. et al. (1985) J. Membrane. Biol. 86, 113-125.
Vetvicka, V., and Lubor, F. (1988) CRC Critical Rev. Ther. Drug Deliv. Sys. 5, 141-170.
Shen, W.C. et al. (1992) Adv. Drug Delivery Rev. 8, 93-113.
Mostov, K.E., and Semister, N.E. (1985) Cell 43, 389-390.
Edwards, P. (1978) British Med. Bull. 34, 55-56.
Conradi, R.A. et al. (1991) Pharm. Res. 8, 1453-1460.
Kaji, H. et al. (1985) Life Sci. 37, 523-530.
Inagaki, M. et al. (1985) Rhinology 23, 213-221.
Gordon, S. et al. (1985) Proc. Natl. Acad. Sci. USA 82, 7419-7423.
Kidron, M. et al. (1982) Life Sci. 31, 2837-2841.
Takaroi, K. et al. (1986) Biochem. Biophys. Res. Comm. 137, 682-687.
Shen, W.C., and Ryser, H.J.P. (1981) Proc. Natl. Acad. Sci. USA 787589-7593.
Broadwell, R.D. et al. (1988) Proc. Natl. Acad. Sci. USA 85, 632-646.
Wan, J. et al. (1992) J. Biol. Chem. 267, 13446-13450.
Sett, R. et al. (1993) J. Infect. Diseases 168, 994-999.
Vitetta, E.S. (1990) J. Clin. Immunol. 10, 15S-18S.
Friden, P.M., and Walus, L.R. (1993) Adv. Exp. Med. Biol. 331, 129-136.
Wan, J. and Shen, W.C. (1991) Pharm. Res. 8, S-5.
Taub, M.E., and Shen, W.C. (1992) J. Cell. Physiol. 150, 283-290.
Yoshikawa, H. et al. (1985) Pharm. Res. 2, 249-251.
Fix, J.A. et al. Am. J. Physiol. 251, G332-G340.
Smith, P. et al. (1992) Adv. Drug Delivery Rev. 8, 253-290.
Wan, J. et al. (1990) J. Cell. Physiol. 145, 9-15.
Yavelow, J. et al. (1983) Cancer. Res. 43, 2454s-2459s.
McConahey, P.C., and Dixon, F.J. (1980) Meth. Enzymol. 70, 221-247.
Lowry, O.H. et al. (1951) J. Biol. Chem. 193, 265-275.
Reznikoff, C.A. et al. (1973) Cancer. Res. 33, 3239-3249; Reznikoff, C.A. et al. (1973) Cancer. Res. 33, 3231-3238.
Landolph, J.R. (1985) Transfomatin assay of established cell lines: Mechanism and Application (ed Kakunaga, T., and Yamasaki, H.) IARC Scientific Publications, Lyon, France pp. 185-201.
Lee, V.H.L. et al. (1991) Critical Reviews in Therapeutic Drug Carrier Systems, CRC Press 8, 91-19. . .

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