Anti-inflammatory and antiallergic cyclic peptides
AssigneeCristalia Produtos Quimicos Farmaceuticos Ltda.
InventorsMônica Ferreiera, Carla Silva, Daniel Pimenta, Fernanda Portaro, Katia Conceição, Marilene Demasi
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Abstract
The present invention refers to synthetic, cyclic peptides containing a sequence of 13 L-amino acids in their primary structure which present anti-inflammatory and antiallergic activities, useful for the treatment of acute or chronic inflammation and/or allergies, being particularly useful for the treatment of acute or chronic allergic asthma. The invention also describes a pharmaceutical composition containing said peptides, its use and a method to treat or prevent acute and/or chronic inflammatory and/or allergic disorders.
Claims14
1- Synthetic, cyclic peptides characterized by comprising 13 amino acids, presenting the amino acid cysteine at positions 4 and 13 and the amino acid lysine at position 11 of the peptide chain and a disulfide bridge between the thiol groups of cysteine residues 4 and 13 which possess ant-inflammatory and/or anti-allergic activity.
2- Peptides according to claim 1 characterized by comprising the consensus sequences selected from the group consisting of:
- (Seq. ID No. 1)
- Ile1-Pro2-Arg3-Cys4-Arg5-Lys6-Met7-Pro8-Gly9-
- Val10-Lys11-Met12-Cys13
- (Seq. ID No. 2)
- Val1-Glu2-Gln3-Cys4-Thr5-Ile6-Ile7-Gly8-Asp9-
- Glu10-Lys11-Asp12-Cys13
- (Seq. ID No. 3)
- Val1-Glu2-Gln3-Cys4-Thr5-Ile6-Ile7-Gly8-Asp9-
- Ala10-Lys11-Asp12-Cys13
- (Seq. ID No. 4)
- Val1-Gln2-Gln3-Cys4-Ser5-Glu6-Ile7-Ala8-Gly9-
- Ala10-Lys11-Pro12-Cys13
- (Seq. ID No. 5)
- Leu1-His2-Arg3-Cys4-Asp5-Lys6-Ile7-Ala8-Asp9-
- Ala10-Lys11-Pro12-Cys13
- (Seq. ID No. 6)
- Ile1-Pro2-Arg3-Cys4-Arg5-Ala6-Met7-Pro8-Gly9-
- Val10-Lys11-Met12-Cys13
- (Seq. ID No. 7)
- Ile1-Pro2-Arg3-Cys4-Arg5-Lys6-Met7-Pro8-Gly9-
- Val10-Lys11-Met12-Cys13-NH2
- (Seq. ID No. 8)
- Ac-Ile1-Pro2-Arg3-Cys4-Arg5-Lys6-Met7-Pro8-Gly9-
- Val10-Lys11-Met12-Cys13
- (Seq. ID No. 9)
- Ac-Ile1-Pro2-Arg3-Cys4-Arg5-Lys6-Met7-Pro8-Gly9-
- Val10-Lys11-Met12-Cys13-NH2
3- Peptides according to claim 1 characterized by the fact that the amino acids are L-amino acids.
4- Peptides according to claim 2 characterized by the fact that the proline residues are individually, alternately or in conjunction substituted by hydroxyproline residues.
5- Peptides according to claim 2 characterized by the fact that the methionine residues are individually, alternately or in conjunction substituted by residues of oxidized methionine.
6- Peptides, according to claim 2, characterized by the fact that the L-amino acids are individually, alternately or in conjunction substituted by D-amino acids.
7- Peptides, according to claim 1 or 2, characterized by being anti-inflammatory and/or anti-allergic.
8- Peptides, according to claim 1 or 2, characterized by being anti-asthmatic.
9- Peptides, according to claim 1, characterized by being inhibitors of trypsin.
10- A pharmaceutical composition characterized by containing a peptide of claim 1 or 2, alone or in combination with at least two of said peptides, or their pharmaceutically acceptable salts, and one or more pharmaceutically acceptable excipient where the peptide is present in a dose effective to treat or prevent acute and/or chronic inflammatory and/or allergic disorders.
11- Pharmaceutical compositions, according to claim 10, characterized by being administered orally, intranasally, intramuscularly or intravenously.
12- Use of at least 1 of the peptides as described in claim 1 or 2, characterized by being employed in the manufacture of a medicine for the treatment or prevention, in a mammal, of acute and/or chronic inflammatory and/or allergic diseases, asthma, rhinitis, arthritis, atopic dermatitis, immune system disturbances, lymphocytic dysfunction during an immune response, tumors, cellular adhesion and/or parasitic diseases.
13- A method to treat or prevent acute and/or chronic inflammatory and/or allergic disorders, characterized by comprising the step of administering, to a mammal, of an effective quantity of at least one of the peptides of claim 1 or 2.
14- A method, according to claim 13, characterized by the fact that the peptides are administered orally, intranasally, intramuscularly or intravenously.