Modified arginine containing lytic peptides and method of making

Details Modified arginine containing lytic peptides and method of making Modified arginine containing lytic peptides and method of making

1995-06-07

1999-10-19

Tsang, Cecilia J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

514 13, 530324, 530325, 930 10, 930 20, A61K 3810, A61K 3816, C07K 708, C07K 1400

Patent

active

059689048

ABSTRACT:
A non-neurotoxin, arginine residue-containing non-naturally occurring lytic peptide comprising a sequence of amino acid residues in sufficient number and arrangement to confer lytic activity to the peptide, wherein the guanido groups of the arginine residues and the .alpha.-amino group of the N-terminal amino acid are sufficiently glyoxylated to impart enhanced tryptic, chymotryptic, and aminopeptidase digestion resistance to the peptide. The compositions of the invention are suitable for in vivo administration. A method of-making the same, to impart enhanced tryptic digestion resistance thereto, comprising glyoxylating the guanido groups of the arginine residues and the .alpha.-- amino group of the N-terminal amino acid with glyoxa containing buffer for sufficient time and at sufficient conditions to glyoxylate the side chain and .alpha.-amino groups to sufficient extent to confer enhanced proteolytic digestion resistance to the peptide.

REFERENCES:
patent: 4355104 (1982-10-01), Hultmark et al.
patent: 4520016 (1985-05-01), Hultmark et al.
patent: 4810777 (1989-03-01), Zasloff
patent: 5045531 (1991-09-01), Berkowitz et al.
patent: 5070188 (1991-12-01), Njieha et al.
patent: 5242902 (1993-09-01), Murphy et al.
patent: 5294605 (1994-03-01), Houghton et al.
patent: 5411942 (1995-05-01), Widmer et al.
patent: 5424290 (1995-06-01), Maloy et al.
patent: 5561107 (1996-10-01), Jaynes et al.
Takahashi, K. J. Biochem. (Tokyo), 81(2), 403-14, Feb. 1977.
Arrowood M. et al. Antimicrob. Agents Chemother., 35(2), 224-7, Feb. 1991.
Habeeb, A.S.F.A., "Determination of Free Amino Groups in Proteins . . . Acid", Anal. Biochem., 14:328-336 (1966).
Liu et al., "Modification of Arginines in Trypsin . . . Cyclohexanedione", Biochem. 7(8) 2886-92 (1968).
Jaynes et al., "In Vitro Cytocidal Effect of Lytic Peptides . . . Cell Lines" Peptide Research, 2:157-160 (1989).
Jaynes, "Lytic Peptides Portend an Innovative Age in the Management . . . Human Disease", Drug News & Perspective, 3:69-78 (1990).
Reed et al., "Enhanced in Vitro Growth of Murine Fibroblast Cells . . . Peptide", Molecular Reproduction & Development, 31:106-113 (1992).
Akerfeldt et al., "Synthetic Peptides as Models for Ion Channel Proteins", Acc. Chem. Res., 26:191-197 (1993).
Arrowood et al., "Hemolytic Properties of Lytic Peptides Active . . . Cryptosporidium Parvum", J. Protozool., 38:161S-163S (1991).
Jaynes et al., "In vitro cytocidal effect of novel lytic peptides on . . . Trypanosoma cruzi", Faseb J., 2:2878-2883 (1988).
Graham et al., "Cytoxic Effect of Amphipathic Cationic Lytic Peptides on . . . Lines", Proc. of Amer. Assoc. for Cancer Res., 35:410 (1994).
Moore et al., "Preliminary Experimental Anti-Cancer . . . Cecropin .beta.", Proc. of Amer. Assoc. for Cancer Res., 35:410 (1994).
Means et al., "Reductive Alkylation of Amino Groups in Proteins", Biochem., 7:2192-2201 (1968).
Takahashi, "The Reaction of Phenylglyoxal with Arginine . . . ", J. Biol. Chem., 243:6171-6179 (1968).
Yankeelov et al., "Methylmaleic Anhydride as a Reversible . . . Modification", Biochem. & Biophysical Research Comm. 42(5):886-891 (1971).
Busby et al., "Chemical Modifications of Lysyl & Arginyl . . . Antitrypsin", Archives of Biochem. & Biophys., 177:552-560 (1976).
Lin et al., "Chemical Modification of Arginine . . . .alpha.-Bungarotoxin", Biochem. et Biophys. Acta., 1159:255-261 (1992).
Patthy et al., "Identification of Functional Arginine . . . Lysozyme", J. Biol. Chem. 250(2) 565-569 (1975).
Gorecki et al., "Non Cationic Substrates of Trypsin", Biochem. & Biophys. Res. Comm., 29(2):189-193 (1967).

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