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US 2014/0235557 A1Published application
Small Efficient Cell Penetrating Peptides Derived From The Scorpion Toxin Maurocalcine
AssigneesCommissariat A L'energie Atomique Et Aux Energies Alternatives, Universite Joseph Fourier, Institut National De La Sante Et De La Recherche Medicale (Inserm)
InventorMichel De Waard
Life of this patent
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Abstract
The invention relates to small cell penetrating peptides (CPP) derived from the scorpion toxin maurocalcine and to their use as vectors for the intracellular delivery of various drugs and agents.
Claims20
Method of using a peptide as a vector for the intracellular delivery of a molecular cargo comprising the step of delivering a complex of said peptide and molecular cargo across a plasma membrane of a cell, wherein said peptide is a maurocalcine derived cell penetrating peptide comprising a sequence:
- Z-X1-X2-X3-X4-X5-X6-X7-Z′,
- wherein:
- X1 represents a hydrophobic amino acid chosen from 2-amino butyric acid, C, W, F, L, I, V, M and A, or another amino acid different from K and R,
- X2 represents a hydrophobic amino acid chosen from I, L, W, F, V, M, A and C,
- X3 represents a basic amino acid chosen from K and R, or another amino acid different from S, T, D and E, such as P,
- X4 represents an amino acid different from K, R, S, T, D and E, such as H, or a hydrophobic amino acid chosen from W, F, L, I, V, M, A and C,
- X5 represents a hydrophobic amino acid chosen from L, W, F, I, V, A and C,
- X6 represents an amino acid other than a basic or hydrophobic amino acid such as Q, a basic amino acid chosen from K and R, or a hydrophobic amino acid chosen from W, F, L, I, V, M, A and C, and
- X7 represents a basic amino acid chosen from R and K, a hydrophobic amino acid chosen from L, W, F, I, V, M, A and C, or another amino acid, with the proviso that the sequence X1 to X7 comprises three or four of said hydrophobic amino acids and one or two of said basic amino acids, and no more than four of said hydrophobic amino acids and two of said basic amino acids,
- Z and Z′ together represent a sequence of no more than 13 amino acids, or Z and/or Z′ are no amino acid, and
- wherein said sequence has a net charge of 0 to +2 when Z and Z′ are no amino acid or of 0 to +3 when Z and/or Z′ are present, considering that D and E have a negative charge, K and R have a positive charge and the other amino acids have no charge.
8 more elements
A peptide, which is a maurocalcine derived cell penetrating peptide comprising of a sequence:
- Z-X1-X2-X3-X4-X5-X6-X7-Z′,
- wherein:
- X1 represents a hydrophobic amino acid chosen from 2-amino butyric acid, C, W, F, L, I, V, M and A, or another amino acid different from K and R,
- X2 represents a hydrophobic amino acid chosen from I, L, W, F, V, M, A and C,
- X3 represents a basic amino acid chosen from K and R, or another amino acid different from S, T, D and E, such as P,
- X4 represents an amino acid different from K, R, S, T, D and E, such as H, or a hydrophobic amino acid chosen from W, F, L, I, V, M, A and C,
- X5 represents a hydrophobic amino acid chosen from L, W, F, I, V, A and C,
- X6 represents an amino acid other than a basic or hydrophobic amino acid such as Q, a basic amino acid chosen from K and R, or a hydrophobic amino acid chosen from W, F, L, I, V, M, A and C, and
- X7 represents a basic amino acid chosen from R and K, a hydrophobic amino acid chosen from L, W, F, I, V, M, A and C, or another amino acid, with the proviso that the sequence X1 to X7 comprises three or four of said hydrophobic amino acids and one or two of said basic amino acids, and no more than four of said hydrophobic amino acids and two of said basic amino acids,
- Z and Z′ together represent a sequence of no more than 13 amino acids, or Z and/or Z′ are no amino acid, and
- wherein said sequence has a net charge of 0 to +2 when Z and Z′ are no amino acid or of 0 to +3 when Z and/or Z′ are present, considering that D and E have a negative charge, K and R have a positive charge and the other amino acids have no charge.
8 more elements
A method to treating a subject in need comprising the step of administering a therapeutically effective amount of a complex comprising of an active agent and a peptide comprising of a sequence:
- Z-X1-X2-X3-X4-X5-X6-X7-Z′,
- wherein:
- X1 represents a hydrophobic amino acid chosen from 2-amino butyric acid, C, W, F, L, I, V, M and A, or another amino acid different from K and R,
- X2 represents a hydrophobic amino acid chosen from I, L, W, F, V, M, A and C,
- X3 represents a basic amino acid chosen from K and R, or another amino acid different from S, T, D and E, such as P,
- X4 represents an amino acid different from K, R, S, T, D and E, such as H, or a hydrophobic amino acid chosen from W, F, L, I, V, M, A and C,
- X5 represents a hydrophobic amino acid chosen from L, W, F, I, V, A and C,
- X6 represents an amino acid other than a basic or hydrophobic amino acid such as Q, a basic amino acid chosen from K and R, or a hydrophobic amino acid chosen from W, F, L, I, V, M, A and C, and
- X7 represents a basic amino acid chosen from R and K, a hydrophobic amino acid chosen from L, W, F, I, V, M, A and C, or another amino acid, with the proviso that the sequence X1 to X7 comprises three or four of said hydrophobic amino acids and one or two of said basic amino acids, and no more than four of said hydrophobic amino acids and two of said basic amino acids,
- Z and Z′ together represent a sequence of no more than 13 amino acids, or Z and/or Z′ are no amino acid, and
- wherein said sequence has a net charge of 0 to +2 when Z and Z′ are no amino acid or of 0 to +3 when Z and/or Z′ are present, considering that D and E have a negative charge, K and R have a positive charge and the other amino acids have no charge.
8 more elements
Dependencies are inferred from the claim text.