US2016095935A1PendingUtilityA1

Conjugates comprising mannan and myelin basic protein (mbp)

38
Assignee: VIANEX S APriority: Jan 25, 2008Filed: Oct 7, 2015Published: Apr 7, 2016
Est. expiryJan 25, 2028(~1.5 yrs left)· nominal 20-yr term from priority
A01K 2267/0325A61K 2039/6087A61K 47/64C07K 7/08C07K 14/4713C07K 7/64A61K 2039/627A61K 39/0008A01K 2207/10A01K 2227/105A61P 37/06A61K 47/48246
38
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Claims

Abstract

A first aspect of the invention relates to a conjugate including mannan and at least one epitope comprising a peptide fragment of a protein selected from myelin basic protein (MBP), myelin oligodentrocyte glycoprotein (MOG) and proteolipid protein (PLP), said peptide fragment being in linear or cyclic form; and wherein said epitope is linked to mannan via a [(Lys-Gly) n ] bridge, where n is an integer from 1 to 10. Further aspects of the invention relate to pharmaceutical compositions comprising said conjugates, and their use in the preparation of a medicament for treating an immune disorder.

Claims

exact text as granted — not AI-modified
1 . A conjugate comprising:
 (i) mannan; and   (ii) at least one epitope comprising a peptide fragment of myelin basic protein (MBP), said peptide fragment being in linear or cyclic form;   wherein said epitope is linked to mannan via a [(Lys-Gly) n ] bridge, where n is an integer from 1 to 10.   
     
     
         2 . (canceled) 
     
     
         3 . A conjugate according to  claim 1 , wherein the epitope comprises a peptide selected from MBP 83-99 , MBP 82-101 , [Ala 86 ]MBP 83-89 , [Ala 88 ]MBP 83-89  [Tyr 89 ]MBP 83-89  and MBP 110-118 , and variants thereof, in linear or cyclic form. 
     
     
         4 . A conjugate according to  claim 1 , wherein the epitope comprises the peptide MBP 83-99 , in linear or cyclic form. 
     
     
         5 . A conjugate according to  claim 1 , wherein the epitope corresponds to the peptide of SEQ ID NO. 1, or a variant thereof: 
       
         
           
                 
               
                   [SEQ ID NO. 1] 
                 
                   H-Glu-Asn-Pro-Val-Val-His-Phe-Phe-Lys-Asn-Ile-Val- 
                 
                     
                 
                   Thr-Pro-Arg-Thr-Pro-OH 
                 
             
                
                
                
                
               
            
           
         
       
       in linear or cyclic form. 
     
     
         6 .- 14 . (canceled) 
     
     
         15 . A conjugate according to  claim 1 , wherein the mannan is reduced mannan. 
     
     
         16 . A conjugate according to  claim 1 , wherein the mannan is oxidised mannan. 
     
     
         17 . A conjugate according to  claim 1 , wherein two or more epitopes, or cyclic counterparts thereof, are linked to mannan. 
     
     
         18 . A conjugate according to  claim 17  wherein the epitopes (or cyclic counterparts thereof) are different. 
     
     
         19 . A mixture comprising two or more conjugates according to  claim 1 . 
     
     
         20 . A mixture according to  claim 19  wherein the conjugates are different. 
     
     
         21 . A pharmaceutical preparation comprising a conjugate according to  claim 1  and a pharmaceutically acceptable carrier, diluent or excipient. 
     
     
         22 .- 26 . (canceled) 
     
     
         27 . A method of treating an immune disorder, said method comprising administering to a subject a conjugate according to  claim 1 . 
     
     
         28 . A method according to  claim 27  wherein the immune disorder is an autoimmune disease. 
     
     
         29 . A method according to  claim 27  wherein the immune disorder is multiple sclerosis (MS). 
     
     
         30 . A method according to  claim 27  wherein the immune disorder is experimental autoimmune encephalomyelitis (EAE). 
     
     
         31 . A method of immunizing a subject against an immune disorder, said method comprising administering to a subject a conjugate according to  claim 1 . 
     
     
         32 . A method according to  claim 27  wherein the conjugate is administered in an amount sufficient to cause suppression of chronic experimental autoimmune encephalomyelitis (EAE). 
     
     
         33 . (canceled) 
     
     
         34 . A process for preparing a conjugate according to  claim 1 , said process comprising the steps of:
 (i) reacting an epitope comprising a peptide fragment of myelin basic protein (MBP), said peptide fragment being in linear or cyclic form, with a peptide bridge [(Lys-Gly) n ], wherein n is an integer from 1 to 10;   (ii) reacting the product formed in step (i) with oxidized mannan; and   (iii) optionally reducing the product formed in step (ii) to form a reduced mannan conjugate.   
     
     
         35 . A vaccine comprising a conjugate according to  claim 1 . 
     
     
         36 . (canceled) 
     
     
         37 . A conjugate according to  claim 1  further comprising:
 an epitope comprising a peptide fragment of myelin oligodentrocyte glycoprotein (MOG); and 
 an epitope comprising a peptide fragment of proteolipid protein (PLP); 
 each peptide fragment being in linear or cyclic form; 
 wherein each epitope is linked to mannan via a [(Lys-Gly) n ] bridge, where n is an integer from 1 to 10. 
 
     
     
         38 . A conjugate according to  claim 1  further comprising one of
 (i) epitope comprising a peptide fragment of myelin oligodentrocyte glycoprotein (MOG); and 
 (ii) an epitope comprising a peptide fragment of proteolipid protein (PLP). 
 
     
     
         39 . A conjugate according to  claim 5  wherein the epitope is linked to mannan via a [(Lys-Gly) 5 ] bridge. 
     
     
         40 . A conjugate according to  claim 1  wherein the peptide has the amino acid sequence of formula (I), 
       
         
           
                 
                 
                 
               
                     
                   ENPVVHFFK 91 NIVTP 96 RTP 
                   (I) 
                 
             
                
               
            
           
         
       
       wherein at least one of K 91  and P 96  is substituted by a natural or unnatural amino acid, wherein said peptide is in linear or cyclic form. 
     
     
         41 . A conjugate according to  claim 40  wherein K 91  is substituted by an amino acid selected from A, R, E, F and Y. 
     
     
         42 . A conjugate according to  claim 40  wherein P 96  is substituted by the amino acid A. 
     
     
         43 . A conjugate according to  claim 40  wherein the peptide is selected from: 
       
         
           
                 
                 
                 
               
                     
                   [R 91 , A 96 ]MBP 83-99   
                   ENPVVHFFRNIVTARTP; 
                 
                     
                     
                 
                     
                   [A 91 , A 96 ]MBP 83-99   
                   ENPVVHFFANIVTARTP; 
                 
                     
                     
                 
                     
                   [E 91 ]MBP 83-99   
                   ENPVVHFFENIVTPRTP; 
                 
                     
                     
                 
                     
                   [F 91 ]MBP 83-99   
                   ENPVVHFFFNIVTPRTP; 
                 
                     
                   and 
                     
                 
                     
                     
                 
                     
                   [Y 91 ]MBP 83-99   
                   ENPVVHFFYNIVTPRTP. 
                 
             
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         44 . A conjugate according to  claim 1  wherein the peptide is selected from the following: 
       
         
           
                 
                 
                 
               
                     
                 
                   peptide analogues 
                     
                   sequence 
                 
                     
                 
                   cyclo(83-99)MBP 83-99   
                   SEQ ID NO. 1 
                   cyclo(83-99)E N P V V H F F K N I V T P R T P 
                 
                     
                 
                   cyclo(83-99)[A 91 ]MBP 83-99   
                   SEQ ID NO. 18 
                   cyclo(83-99)E N P V V H F F  A  N I V T P R T P 
                 
                     
                 
                   cyclo(83-99)[R 91 ]MBP 83-99   
                   SEQ ID NO. 19 
                   cyclo(83-99)E N P V V H F F  R  N I V T P R T P 
                 
                     
                 
                   cyclo(83-99)[F 91 ]MBP 83-99   
                   SEQ ID NO. 15 
                   cyclo(83-99)E N P V V H F F  F  N I V T P R T P 
                 
                     
                 
                   cyclo(83-99)[Y 91 ]MBP 83-99   
                   SEQ ID NO. 16 
                   cyclo(83-99)E N P V V H F F  Y  N I V T P R T P 
                 
                     
                 
                   cyclo(83-99)[E 91 ]MBP 83-99   
                   SEQ ID NO. 14 
                   cyclo(83-99)E N P V V H F F  E  N I V T P R T P 
                 
                     
                 
                   cyclo(83-99)[A 91 , A 96 ]MBP 83-99   
                   SEQ ID NO. 13 
                   cyclo(83-99)E N P V V H F F  A  N I V T  A  R T P 
                 
                     
                 
                   cyclo(83-99)[R 91 , A 96 ]MBP 83-99   
                   SEQ ID NO. 12 
                   cyclo(83-99)E N P V V H F F  R  N I V T  A  R T P 
                 
                     
                 
                   cyclo(83-99)[F 91 , A 96 ]MBP 83-99   
                   SEQ ID NO. 20 
                   cyclo(83-99)E N P V V H F F  F  N I V T  A  R T P 
                 
                     
                 
                   cyclo(83-99)[Y 91 , A 96 ]MBP 83-99   
                   SEQ ID NO. 21 
                   cyclo(83-99)E N P V V H F F  Y  N I V T  A  R T P 
                 
                     
                 
                   cyclo(83-99)[S 91 , A 96 ]MBP 83-99   
                   SEQ ID NO. 22 
                   cyclo(83-99)E N P V V H F F  S  N I V T  A  R T P.

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