US2014249091A1PendingUtilityA1
Delta-Opioid Receptor Selective Analgesics
Est. expiryDec 8, 2028(~2.4 yrs left)· nominal 20-yr term from priority
C07K 9/001A61P 25/00C07K 7/06A61P 29/02
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Claims
Abstract
Methods and materials are provided for the production of glycosylated peptides that exhibit high affinity and specificity for delta opioid receptors. The methods and materials of the present invention may be used for treatment of conditions involving pain, such as acute pain and nociceptic pain, neuralgia and myalgia.
Claims
exact text as granted — not AI-modified1 . A glycosylated peptide comprising the following amino acid sequence:
SEQ ID NO 1
X1-X2-X3-X4-X5-X6-X7-W
wherein:
W is selected from NH2 and OH;
X1 is Y;
X2 is selected from dAla and dMet;
X3 is F;
X4 is selected from H, E, D and Q;
X5 is selected from L, V, I, C and Y;
X6 is selected from M, A, V, I, D, L, C, P and H;
X7 is selected from S, T, D, G, N, A and K;
and wherein at least one of X3, X6 and X7 is glycosylated.
2 . A glycosylated peptide according to claim 1 , wherein at least one of X3, X6 and X7 is glycosylated with a sugar residue selected from the group consisting of glucose; galactose; xylose; fructose; mannose; fucose; ribose; deoxyribose; arabinose; rhamnose; sucrose; trehalose; saccharose; maltose; and lactose.
3 . A glycosylated peptide according to claim 1 , comprising an amino acid sequence selected from the group consisting of:
SEQ ID NO 2
Y-dMet-F-H-L-M-Ser(beta-D-Glc)NH2;
SEQ ID NO 3
Y-dAla-F-H-L-A-Ser(beta-D-Glc)NH2;
SEQ ID NO 4
Y-dMet-F-H-L-M-Thr(beta-D-Glc)NH2;
SEQ ID NO 5
Y-dAla-F-H-L-A-Thr(beta-D-Glc)NH2;
SEQ ID NO 6
Y-dMet-F-H-L-M-dSer(beta-D-Glc)NH2;
and
SEQ ID NO 7
Y-dAla-F-H-L-A-dSer(beta-D-Glc)NH2.
4 . A glycosylated peptide comprising the following amino acid sequence:
SEQ ID NO 8
X1-X2-X3-X4-X5-X6-X7-W
wherein:
W is selected from NH2 and OH;
X1 is Y;
X2 is selected from dAla and dMet;
X3 is selected from F and A;
X4 is selected from H, E, D and Q;
X5 is selected from Nva, Nle, L, V, I, C and Y;
X6 is selected from Nva, Nle, L, V, I, M, A, D, C, P and H;
X7 is selected from S, dSer, T, dThr, D, G, N, A and K;
and wherein at least one of X3, X6 and X7 is glycosylated.
5 . A glycosylated peptide according to claim 4 , wherein at least one of X3, X6 and X7 is glycosylated with a sugar residue selected from the group consisting of glucose, galactose, xylose, fructose, mannose, fucose, ribose, deoxyribose, arabinose, rhamnose, sucrose, trehalose, saccharose, maltose, and lactose.
6 . A glycosylated peptide according to claim 4 , comprising an amino acid sequence selected from the group consisting of:
SEQ ID NO 9
Y-dAla-F-E-Nva-Nva-Ser(beta-D-Glc)NH2;
SEQ ID NO 10
Y-dAla-F-E-Nle-Nle-Ser(beta-D-Glc)NH2;
SEQ ID NO 11
Y-dAla-F-E-Nva-Nva-Thr(beta-D-Glc)NH2;
SEQ ID NO 12
Y-dAla-F-H-Nle-Nle-Thr(beta-D-Glc)NH2;
SEQ ID NO 13
Y-dAla-F-H-Nva-Nva-dSer(beta-D-Glc)NH2;
and
SEQ ID NO 14
Y-dAla-F-H-Nle-Nle-dSer(beta-D-Glc)NH2.
7 . A glycosylated peptide comprising the following amino acid sequence:
SEQ ID NO 15
X1-X2-X3-X4-X5-X6-X7-Z-W
wherein:
X1 is Y;
X2 is selected from dAla and dMet;
X3 is F;
X4 is selected from H, E, D and Q;
X5 is selected from L, V, Nva, Nle, I, C and Y;
X6 is selected from L, V, Nva, Nle, I, M, A, D, L, C, P and H;
X7 is selected from S, dSer, T, dThr, D, G, N, A and K;
Z is selected from a sequence of 0 to 5 amino acids;
W is selected from NH2 and OH;
and wherein at least one of X3, X6 and X7 is glycosylated.
8 . A glycopeptide of claim 7 , wherein at least one of X3, X6 and X7 is glycosylated with a sugar residue selected from the group consisting of glucose; galactose; xylose; fructose; mannose; fucose; ribose; deoxyribose; arabinose; rhamnose; sucrose; trehalose; saccharose; maltose; and lactose.
9 . A glycosylated peptide comprising the following amino acid sequence:
SEQ ID NO 16
X1-X2-X3-X4-X5-X6-X7-Z-W
wherein:
X1 is selected from Y; Dmt and Tmt;
X2 is selected from dAla; dMet; dVal; and B;
X3 is selected from F; Tic and Nmf;
X4 is selected from H, E, D; Q and F;
X5 is selected from L, V, I, C, Y, A, Nva and Nle;
X6 is selected from M, V, I, D, L, C, P, H, A, T, Nva and Nle;
X7 is selected from D, G, N, S, A, K, T, dSer, and dThr;
Z is selected from a sequence of 0 to 5 amino acids;
W is selected from NH2 and OH;
and wherein at least one of X3, X6 and X7 is glycosylated, each of A, C, D, F, G, H, I, K, L, M, N, P, Q, S, T, V and Y are understood to represent commonly known amino acids, and wherein:
Dmt=2,5-dimethyltyrosine
Tic=tetrahydroisoquinoline-3-carboxylic acid
B=alpha-aminoisobutyric acid
Tmt=2,5,beta-trimethyltyrosine (R,S isomer)
Nmf=N-methylphenylalanine
Nva=L-norvaline
Nle=L-norleucine
10 . A glycosylated peptide according to claim 9 , wherein at least one of X3, X6 and X7 is glycosylated with a sugar residue selected from the group consisting of glucose; galactose; xylose; fructose; mannose; fucose; ribose; deoxyribose; arabinose; rhamnose; sucrose; trehalose; saccharose; maltose; and lactose.
11 . A glycosylated peptide according to claim 9 , wherein, comprising an amino acid sequence selected from the group consisting of:
SEQ ID NO 17
Y-dAla-F-E-Nle-Nle-dThr(beta-D-Glc)NH2;
SEQ ID NO 18
Y-dAla-F-E-Nle-Nle-dSer(beta-D-Glc)NH2;
SEQ ID NO 19
Y-dAla-F-E-Nle-Nle-Thr(beta-D-Rhamnoside)NH2;
SEQ ID NO 20
Y-dAla-F-E-Nle-Nle-Thr(beta-Lactoside)NH2;
SEQ ID NO 21
Y-dAla-F-E-I-I-Thr(beta-D-Glc)NH2;
SEQ ID NO 22
Y-dAla-F-E-V-V-Ser(beta-D-Glc)NH2;
SEQ ID NO 23
Dmt-dAla-F-E-Nle-Nle-Thr(beta-D-Glc)NH2;
SEQ ID NO 24
Y-dAla-Tic-E-Nle-Nle-Thr(beta-D-Glc)NH2;
SEQ ID NO 25
Y-B-F-E-Nle-Nle-Thr(beta-D-Glc)NH2;
SEQ ID NO 26
Tmt-dAla-F-E-Nle-Nle-Thr(beta-D-Glc)NH2;
and
SEQ ID NO 27
Y-dAla-Nmf-E-Nle-Nle-Thr(beta-D-Glc)NH2.
12 . A method of treating a subject suffering from a neurological disease or disorder, comprising administering the glycosylated peptide of claim 1 to the subject.
13 . The method of claim 12 , wherein the neurological disease or disorder involves acute or nociceptic pain.
14 . A method of treating a subject suffering from a neurological disease or disorder, comprising administering the glycosylated peptide of claim 4 to the subject.
15 . The method of claim 14 , wherein the neurological disease or disorder involves acute or nociceptic pain.
16 . A method of treating a subject suffering from a neurological disease or disorder, comprising administering the glycosylated peptide of claim 9 to the subject.
17 . The method of claim 16 , wherein the neurological disease or disorder involves acute or nociceptic pain.Join the waitlist — get patent alerts
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