Cell penetrating peptides
AssigneesOxford University Innovation Limited, United Kingdom Research and Innovation
InventorsMatthew Wood, Suzan Hammond, Melissa Bowerman, Michael Gait, Frank Adendroth, Graham McClorey
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Abstract
The present invention relates to peptides, in particular cell penetrating peptides, of 40 amino acid residues or less comprising at least one directly glycosylated amino residue and one or more arginine rich arm domains, and to conjugates of such cell penetrating peptides with a therapeutic molecule. The present invention further relates to the use of the peptides or conjugates in methods of treatment or as a medicament, especially in the treatment of genetic disorders of the central nervous system.
Claims21
A peptide comprising a sequence selected from the following sequences:
- (SEQ ID NO. 8)
- RXRRBRRXRQFLRXRBRXRS*,
- (SEQ ID NO. 11)
- S*RXRRBRRXRQFLRXRBRXR,
- (SEQ ID NO. 14)
- RXRRBRRXRS*FLRXRBRXR,
- (SEQ ID NO. 47)
- RXRRBRRXRS*FLRXRBRXRS*FL,
- (SEQ ID NO. 50)
- RXRRBRRXRS*FQRXRBRXR,
- (SEQ ID NO. 52)
- RXRRBRRXRS*WFRXRBRXR,
- and
- (SEQ ID NO. 53)
- RXRRBRRXRS*QFRXRBRXR,
- wherein X is aminohexanoic acid, B is beta-alanine, and wherein S* represents L-serine glycosylated with D-Glucose sugar.
A peptide selected from the following sequences:
- RXRRBRRXRS*FLRXRBRXR (SEQ ID NO.14), RXRRBRRFS*RBRXR (SEQ ID NO.17), RXRRBRRZS*RBRXR (SEQ ID NO.73), RXRRBRRFS11*RBRXR (SEQ ID NO.74), RBRBRS*RBRBR (SEQ ID NO.70) and RXRXRS*RXRXR (SEQ ID NO.71), wherein X is aminohexanoic acid, B is beta-alanine, Z is 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, S* represents L-serine glycosylated with D-Glucose sugar, and S1* represents D-serine glycosylated with D-Glucose sugar.
A peptide comprising a sequence selected from the following sequences:
- (SEQ ID NO. 12)
- RXRRBRRXRS*QFLS*RXRBRXR,
- (SEQ ID NO. 13)
- RXRRBRRXRS*QFLRXRBRXR,
- (SEQ ID NO. 43)
- RXRRBRRXRS*FRXRBRXR,
- and
- (SEQ ID NO. 44)
- RXRRBRRXRS*RXRBRXR,
- wherein X is aminohexanoic acid, B is beta-alanine and S* represents L-serine glycosylated with D-Glucose sugar.
A peptide comprising a sequence selected from the following sequences:
- (SEQ ID NO. 51)
- RXRRBRRFS1*RXRBR,
- (SEQ ID NO. 111)
- RXRRBRRFS2*RXRBR,
- (SEQ ID NO. 112)
- RXRRBRRFS3*RXRBR,
- (SEQ ID NO. 116)
- RXRRBRRZS*RXRBR,
- (SEQ ID NO. 157)
- RXRRBRRFS4*RXRBR,
- (SEQ ID NO. 158)
- RXRRBRRFS6*RXRBR,
- (SEQ ID NO. 160)
- RXRRBRRFS5*RXRBR,
- (SEQ ID NO. 168)
- RXRRBRRS1*RXRBR,
- (SEQ ID NO. 169)
- RXRRBRRS2*RXRBR,
- (SEQ ID NO. 170)
- RXRRBRRS3*RXRBR,
- (SEQ ID NO. 171)
- RXRRBRRS4*RXRBR,
- (SEQ ID NO. 172)
- RXRRBRRN*RXRBR,
- (SEQ ID NO. 173)
- RXRRBRRS6*RXRBR,
- and
- (SEQ ID NO. 175)
- RXRRBRRS5*RXRBR,
- wherein X is aminohexanoic acid, B is beta-alanine, Z is 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,
- S* represents L-serine glycosylated with D-Glucose sugar,
- S1* represents D-serine glycosylated with D-Glucose sugar,
- S2* represents L-serine glycosylated with an L-Glucose sugar,
- S3* represents L-serine glycosylated with a D-Mannose sugar,
- S4* represents L-serine glycosylated with a D-Lactose sugar,
- N* represents L-asparagine glycosylated with a D-2-Acetylamino Glucose sugar,
- S5* represents L-serine glycosylated with a D-2-Acetylamino Glucose sugar, and
- S6* represents L-serine glycosylated with a Galactose sugar.
A peptide comprising a sequence selected from the following sequences:
- (SEQ ID NO. 17)
- RXRRBRRFS*RBRXR,
- (SEQ ID NO. 45)
- RXRRBRRS*FQILYRBRXR,
- (SEQ ID NO. 46)
- RXRRBRRS*FLRBRXR,
- (SEQ ID NO. 55)
- RXRRBRRS*RBRXR,
- (SEQ ID NO. 67)
- RXRRBRRS*S*RBRXR,
- (SEQ ID NO. 68)
- RXRRBRRS*S*S*RBRXR,
- (SEQ ID NO. 73)
- RXRRBRRZS*RBRXR,
- (SEQ ID NO. 74)
- RXRRBRRFS1*RBRXR,
- (SEQ ID NO. 75)
- RXRRBRRFS2*RBRXR,
- (SEQ ID NO. 76)
- RXRRBRRFS3*RBRXR,
- (SEQ ID NO. 77)
- RXRRBRRFS4*RBRXR,
- (SEQ ID NO. 78)
- RXRRBRRFN*RBRXR,
- (SEQ ID NO. 79)
- RXRRBRRFS6*RBRXR,
- (SEQ ID NO. 159)
- RXRRBRRFS5*RBRXR,
- and
- (SEQ ID NO. 162)
- RXRRBRRS1*RBRXR,
- wherein X is aminohexanoic acid, B is beta-alanine, Z is 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,
- S* represents L-serine glycosylated with D-Glucose sugar,
- S′* represents D-serine glycosylated with D-Glucose sugar,
- S2* represents L-serine glycosylated with an L-Glucose sugar,
- S3* represents L-serine glycosylated with a D-Mannose sugar,
- S4* represents L-serine glycosylated with a D-Lactose sugar,
- N* represents L-asparagine glycosylated with a D-2-Acetylamino Glucose sugar,
- S5* represents L-serine glycosylated with a D-2-Acetylamino Glucose sugar, and
- S6* represents L-serine glycosylated with a Galactose sugar.
A peptide comprising a sequence selected from the following sequences:
- (SEQ ID NO. 18)
- RBRRBRRBRS*FLRBRBRBR,
- (SEQ ID NO. 29)
- RBRRBRRBRS*FLRBRBR,
- (SEQ ID NO. 30)
- RBRRBRRBRS*FLRBR,
- (SEQ ID NO. 31)
- RBRRBRRBRS*FLR,
- (SEQ ID NO. 32)
- RBRRBRRBRS*FL,
- (SEQ ID NO. 33)
- RBRRBRRBRS*FLRBRBRR,
- (SEQ ID NO. 34)
- RBRRBRRBRS*FLRBRRR,
- and
- (SEQ ID NO. 35)
- RBRRBRRBRS*FLRRRR,
- wherein B is beta-alanine and S* represents L-serine glycosylated with D-Glucose sugar.
A peptide comprising a sequence selected from the following sequences:
- (SEQ ID NO. 24)
- RRBRRBRS*FLRBRBRBR,
- (SEQ ID NO. 25)
- RBRRBRS*FLRBRBRBR,
- (SEQ ID NO. 26)
- RRBRS*FLRBRBRBR,
- (SEQ ID NO. 27)
- RBRS*FLRBRBRBR,
- (SEQ ID NO. 28)
- RS*FLRBRBRBR,
- (SEQ ID NO. 36)
- RBRRBRRRS*FLRBRBRBR,
- (SEQ ID NO. 37)
- RBRRRRRS*FLRBRBRBR,
- and
- (SEQ ID NO. 38)
- RRRRRRS*FLRBRBRBR,
- wherein B is beta-alanine and S* represents L-serine glycosylated with D-Glucose sugar.
Dependencies are inferred from the claim text.