Methods and Devices for Analytical Sensing of Biogenic Amines

Abstract

Disclosed herein are chromogenic response polymers and methods and devices that utilize the disclosed polymers which are suitable for use in detecting the presence of and identity of biogenic amines.

1 . A method for detecting the presence of a biogenic amine, comprising:
 a) providing a chromogenic-responsive polymer;   b) contacting the polymer in step (a) with an analyte; and   c) detecting a chromogenic response.   
     
     
         2 . A method according to  claim 1 , wherein the polymer comprises a plurality of residues chosen from:
 ii) thiophenyl;   iii) furanyl;   iv) pyrrolyl;   v) fluorenyl;   vi) 1,4-phenylene ethynylene; and   vii) 1,4-phenylene.   
     
     
         3 . A method according to  claim 1 , wherein the polymer is chosen from: 
       
         
           
           
               
               
           
         
         wherein the index n has a value such that the polymer has a molecular weight of from about 1,000 Da to about 1,000,000 Da; the indices a+b=n; 
         X is chosen from S, N, or O; 
         R and R 1  are each independently chosen from: 
         i) —H; 
         ii) —OM; 
         iii) —CO 2 M; 
         iv) —SO 3 M; 
         v) —PO 3 M 2 ; and 
         vi) —OCH 3 ; 
         R 2  is chosen from: 
         i) —H; 
         i) —OM; 
         ii) —CO 2 M; 
         iii) —SO 3 M; 
         iv) —PO 3 M 2 ; and 
         v) —OCH 3 ; 
         R 3  and R 4  are each independently chosen from: 
         i) —H; 
         ii) —OM; 
         iii) —CO 2 M; 
         iv) —SO 3 M; 
         ii) —PO 3 M 2 ; and 
         vi) —OCH 3 ; or 
         R 3  and R 4  can be taken together to form a ring together with the two phenyl rings to form a fused ring having from 5 to 7 carbon atoms; 
         M is hydrogen, an alkali metal, an alkali earth metal, a transition metal, or a lanthanide metal; 
         L, L 1 , L 3 , and L 4  are each independently chosen from: 
         i) —(CR 5a R 5b ) m —; or 
         ii) —[O(CR 5a R 5b ) m ] k —; and 
         L 2  and L 5  are each chosen from: 
         i) —(CR 5a R 5b ) m —; or 
         ii) —[O(CR 5a R 5b ) p ] k —; and 
         iii) —(CR 5a R 5b ) j (CH═CH)(CR 5a R 5b ) j —; 
         iv) —(CR 5a R 5b ) j (C≡C)(CR 5a R 5b ) j —; 
         R 5a  and R 5b  are each independently hydrogen or methyl; 
         the index j is an integer from 0 to 10; 
         the index k is an integer from 1 to 20; 
         the index m is an integer from 0 to 10; and 
         the index p is an integer from 2 to 20. 
       
     
     
         4 . A method according to  claim 1 , wherein the polymer has the formula: 
       
         
           
           
               
               
           
         
         wherein R is chosen from: 
         i) —CO 2 M; 
         ii) —SO 3 M; or 
         iii) —PO 3 M 2 ; 
         M is chosen from Na + , Co 2+ , Cu 2+ , Fe 2+ , Ni 2+ , Ln 3+ , Eu 3+ , and Tb 3+ ; 
         L is chosen from: 
         i) —CH 2 —; 
         ii) —CH 2 CH 2 —; 
         iii) —CH 2 CH 2 CH 2 —; or 
         iv) —CH 2 CH 2 CH 2 CH 2 —; and 
         the index n is an integer such that the molecular weight of the polymer is from about 2,000 Da to about 12,000 Da. 
       
     
     
         5 . A method according to  claim 1 , wherein the polymer has the formula: 
       
         
           
           
               
               
           
         
         wherein M is chosen from Na + , Co 2+ , Cu 2+ , and Ni 2+ ; and 
         the index n is an integer such that the molecular weight of the polymer is from about 5,000 Da to about 10,000 Da. 
       
     
     
         6 . A method according to  claim 1 , wherein the analyte comprises one or more amines. 
     
     
         7 . A method according to  claim 1 , wherein the analyte comprises one or more amines having the formula:
   R 12 —(CR 10a R 10b ) p —(Y) r —(CR 10c R 10d ) q —NH 2  
   wherein R 10a , R 10b , R 10c , and R 10d  are each independently chosen from:   i) hydrogen;   ii) methyl; and   iii) —NH 2 ;   the index p is an integer from 0 to 6;   the index q is an integer from 0 to 6;   Y is:   i) —NH—; or   ii) —(CR 11a R 11b ) s NH 2 ;   R 11a  and R 11b  are each independently:   i) hydrogen; or   ii) methyl;   the index r is 0 or 1;   the index s is an integer from 1 to 6; and   R 12  is chosen from:   ii) hydrogen;   iii) —NH 2 ;   iv) heterocyclic;   v) phenyl; or   vi) heteroaryl.   
     
     
         8 . A method according to  claim 1 , wherein the analyte comprises one or more amines chosen from: 
       
         
           
           
               
               
           
         
       
     
     
         9 . A method according to  claim 1 , wherein the analyte further comprises a solvent. 
     
     
         10 . A method according to  claim 9 , wherein the solvent is water. 
     
     
         11 . A method according to  claim 9 , wherein the solvent is chosen from a C 1 -C 10  alcohol, a C 3 -C 6  ester, a C 3 -C 6  ketone, a C 4 -C 8  ether, a C 1 -C 5  nitrile, a C 1 -C 4  di-alkylformamide, a C 1 -C 4  di-alkylsulfoxide, and mixtures thereof. 
     
     
         12 . A method according to  claim 1 , wherein the analyte further comprises a solvent chosen from water, acetonitrile, dimethylformamide, dimethylsulfoxide, methyl ethyl ketone, methyl acetate, ethyl acetate, and methyl tert-butyl ether. 
     
     
         13 . A method according to  claim 1 , wherein the analyte further comprises a buffer. 
     
     
         14 . A method according to  claim 1 , wherein the pH of the analyte is from about 6 to about 8. 
     
     
         15 . A method according to  claim 1 , wherein the chromogenic response is ultra violet absorption or emission. 
     
     
         16 . A method according to  claim 1 , wherein the chromogenic response is visible light absorption or emission. 
     
     
         17 . A method according to  claim 1 , wherein the analyte is taken from a food source. 
     
     
         18 - 39 . (canceled)