IP Library Granted Patent US 9,708,377
Granted Patent B2
US 9,708,377 · App. 15/032,454 · Granted Jul 18, 2017

Scorpion toxin analogue and method for treating autoimmune diseases

Inventors: Raymond S. Norton (Victoria, AU); Serdar Kuyucak (New South Wales, AU); M Harunur Rashid (New South Wales, AU); Michael Pennington (Shelbyville, KY); Christine Beeton (Pearland, TX)
Assignees: Monash University; Baylor College of Medicine; Peptides International, Inc.
C07K14/43522A61K39/00A61K38/00
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Quick Facts
Patent No.
US 9,708,377
App. No.
15/032,454
Granted
Jul 18, 2017
Kind
B2
Abstract

A novel peptide analogue of the Heterometrus spinnifer toxin HsTX1 is disclosed along with its application as, for example, a therapeutic agent for treating an autoimmune disease such as multiple sclerosis (MS) or rheumatoid arthritis (RA). The analogue comprises a peptide with an amino acid substitution at amino acid position 14 of the wild-type (WT) peptide sequence (or a position corresponding to position 14 of the WT peptide sequence). The analogue exhibits selectivity for Kv1.3 over Kv1.1 and other potassium channels relative to the WT peptide.

Claims (39)

1. A peptide analogue of Heterometrus spinnifer toxin HsTX1 comprising amino acid sequence SEQ ID NO:1, wherein the peptide analogue has an amino acid substitution corresponding to position 14 of SEQ ID NO:1 selected from the group consisting of an arginine (R) to phenylalanine (F) substitution, and an arginine (R) to 2-aminobutyric acid (Abu) substitution.

2. A method of inhibiting T lymphocyte proliferation in a subject, said method comprising administering to the subject an effective amount of a peptide analogue of Heterometrus spinnifer toxin HsTX1 comprising amino acid sequence SEQ ID NO:1, wherein the peptide analogue has an amino acid substitution corresponding to position 14 of SEQ ID NO:1, optionally in combination with a pharmaceutically acceptable carrier.

3. The method of claim 2 , wherein the amino acid substitution corresponding to position 14 of SEQ ID NO:1is selected from the group consisting of an arginine (R) to alanine (A) substitution (ie an R→A substitution), an arginine (R) to valine (V) substitution (ie an R→V substitution), an arginine (R) to phenylalanine (F) substitution (ie an R→F substitution), and an arginine (R) to 2-aminobutyric acid (Abu) substitution (ie an R→Abu substitution).

4. The method of claim 2 , wherein the amino acid substitution corresponding to position 14 of SEQ ID NO:1 is an arginine (R) to alanine (A) substitution (ie an R→A substitution).

5. The method of claim 2 , wherein the peptide analogue comprises an amino acid sequence selected from the group consisting of:

(SEQ ID NO: 2)

ASCRTPKDCADPCAKETGCPYGKCMNRKCKCNRC; 

(SEQ ID NO: 3)

ASCRTPKDCADPCVKETGCPYGKCMNRKCKCNRC; 

(SEQ ID NO: 4)

ASCRTPKDCADPCFKETGCPYGKCMNRKCKCNRC; 

and

(SEQ ID NO: 5) 

ASCRTPKDCADPCXKETGCPYGKCMNRKCKCNRC. 

where X is 2-aminobutyric acid (Abu).

6. The method of claim 2 , wherein the peptide analogue is a peptide that shows disulphide bridging between C3 and C24, C9 and C29, C13 and C31, and C19 and C34.

7. The method of claim 2 , wherein the peptide analogue consists of the amino acid sequence SEQ ID NO: 2.

8. The method of claim 2 , wherein the peptide analogue is in an isolated form.

9. The method of claim 2 , wherein the peptide analogue further comprises an amidated C-terminus.

10. A method of treating an autoimmune disease in a subject, said method comprising administering to the subject an effective amount of a peptide analogue of Heterometrus spinnifer toxin HsTX1 comprising amino acid sequence SEQ ID NO:1, wherein the peptide analogue has an amino acid substitution corresponding to position 14 of SEQ ID NO:1, optionally in combination with a pharmaceutically acceptable carrier.

11. The method of claim 10 , wherein the autoimmune disease to be treated is an autoimmune disease mediated by T EM cells.

12. The method of claim 10 , wherein the autoimmune disease to be treated is multiple sclerosis (MS) or rheumatoid arthritis (RA).

13. The method of claim 10 , wherein the amino acid substitution corresponding to position 14 of SEQ ID NO:1 is selected from the group consisting of an arginine (R) to alanine (A) substitution (ie an R→A substitution), an arginine (R) to valine (V) substitution (ie an R→V substitution), an arginine (R) to phenylalanine (F) substitution (ie an R→F substitution), and an arginine (R) to 2-aminobutyric acid (Abu) substitution (ie an R→Abu substitution).

14. The method of claim 10 , wherein the amino acid substitution corresponding to position 14 of SEQ ID NO:1 is an arginine (R) to alanine (A) substitution (ie an R→A substitution).

15. The method of claim 10 , wherein the peptide analogue comprises an amino acid sequence selected from the group consisting of:

(SEQ ID NO: 2)

ASCRTPKDCADPCAKETGCPYGKCMNRKCKCNRC;

(SEQ ID NO: 3)

ASCRTPKDCADPCVKETGCPYGKCMNRKCKCNRC;

and

(SEQ ID NO: 4)

ASCRTPKDCADPCFKETGCPYGKCMNRKCKCNRC;

(SEQ ID NO: 5)

ASCRTPKDCADPCXKETGCPYGKCMNRKCKCNRC,

where X is 2-aminobutyric acid (Abu).

16. The method of claim 10 , wherein the peptide analogue is a peptide that shows disulphide bridging between C3 and C24, C9 and C29, C13 and C31, and C19 and C34.

17. The method of claim 10 , wherein the peptide analogue consists of the amino acid sequence SEQ ID NO: 2.

18. The method of claim 10 , wherein the peptide analogue is in an isolated form.

19. The method of claim 10 , wherein the peptide analogue further comprises an amidated C-terminus.

Assignments (8)
RELEASE OF SECURITY INTEREST Recorded Apr 1, 2022
From: RENASANT BANK
To: PEPTIDES INTERNATIONAL, LLC
Reel/Frame 059470/0515 →
SECURITY INTEREST Recorded Dec 4, 2019
From: PEPTIDES INTERNATIONAL, LLC
To: RENASANT BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 051179/0411 →
ENTITY CONVERSION Recorded Dec 3, 2019
From: PEPTIDES INTERNATIONAL, INC.
To: PEPTIDES INTERNATIONAL, LLC
Reel/Frame 051280/0958 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2016
From: NORTON, RAYMOND
To: MONASH UNIVERSITY
Reel/Frame 039084/0195 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2016
From: BEETON, CHRISTINE
To: BAYLOR COLLEGE OF MEDICINE
Reel/Frame 039084/0287 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2016
From: KUYUCAK, SERDAR; RASHID, M. HARUNUR
To: THE UNIVERSITY OF SYDNEY, A BODY CORPORATE
Reel/Frame 039084/0493 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2016
From: PENNINGTON, MICHAEL
To: PEPTIDES INTERNATIONAL, INC.
Reel/Frame 039084/0536 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2016
From: THE UNIVERSITY OF SYDNEY, A BODY CORPORATE
To: MONASH UNIVERSITY
Reel/Frame 039085/0947 →
Continuity (1)
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