Cyclic beta-sheet peptides useful as apoptotic/cytotoxic cancer agents
AssigneeThe University of Toledo
InventorsChanning L. Hinman, Charles A. Smith
Life of this patent
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Abstract
Peptides and pharmaceutical compositions of matter useful as cytotoxic compositions particularly for, but not limited to, treatment of cancers, that includes a synthetic peptide whose amino acid sequence is different from an initial loop of cobra cardiotoxin.
Claims28
A pharmaceutical composition of matter useful as a cytotoxic agent, comprising a synthetic peptide whose amino acid sequence differs from loop 1 of a cobra cardiotoxin in which a disulfide bond occurs between two Cys residues.
A pharmaceutical composition comprising a therapeutic amount of the peptide at least one of Seq. ID Nos. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and 12 in which a disulfide bond occurs between the Cys and Cys residues.
A pharmaceutical composition of matter useful as a cytotoxic agent comprising a peptide whose amino acid sequence comprises one of the following sequences:
- Leu-Lys-Cys4-Lys-Leu-7-Pro-Leu-10-Tyr-Lys-Thr-Cys, where 4 is Asn or Gln;
- 7is Val or Ile;
- 10 is Phe or Ala.
A cytotoxic composition that induces apoptosis comprising at least one of the Seq. ID Nos. 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10.
A peptide composition of Seq. ID No. 1, comprising L-amino acids, having a cyclic structure and a disulfide bond between residues 3 and 14.
A peptide composition comprising Seq. ID No. 6 synthesized with and composed of D-amino acids, having a cyclic structure due to the presence of a disulfide bond between the Cys residues.
A peptide composition comprising Seq. ID No. 2 comprising L-amino acids, having a cyclic structure and a disulfide bond between residues 3 and 14.
A peptide composition comprising Seq. ID No. 7 comprising D-amino acids, having a cyclic structure due to the presence of a disulfide bond between the Cys residues.
A peptide composition comprising Seq. ID No. 3 comprising L-amino acids, having a cyclic structure and a disulfide bond between residues 3 and 14.
A peptide composition comprising Seq. ID No. 8 comprising D-amino acids, having a cyclic structure due to the presence of a disulfide bond between the Cys residues.
A peptide composition comprising Seq. ID No. 4 comprising L-amino acid, having a cyclic structure and a disulfide bond between residues 3 and 14.
A peptide composition comprising Seq. ID No. 9 comprising D-amino acids, having a cyclic structure due to the presence of a disulfide bond, between the Cys residues.
A peptide composition comprising Seq. ID No. 5 comprising L-amino acids, having a cyclic structure and a disulfide bond between residues 3 and 14.
A peptide composition comprising Seq. ID No. 10 comprising D-amino acids, having a cyclic structure due to the presence of a disulfide bond between the Cys residues.
A peptide composition comprising Seq. ID No. 12 comprising L-amino acids, having a cyclic structure and a disulfide bond between residues 3 and 14.
A method of making the D-amino acid peptides of Seq. ID Nos. 6, 7, 8, 9, and 10 in which the D-amino acid peptide is synthesized sequentially in an opposite direction from that of a corresponding L-amino acid peptide of Seq. ID Nos. 1, 2, 3, 4 and 5, respectively, wherein the opposite direction is from amino terminus to carboxyl terminus.
Dependencies are inferred from the claim text.