Surface modifying composition

Abstract

Alkanethiols of formula (1) and the enantimomers of the alkanethiol of formula (1): HS-L-Q-T  (1), and disulfides of formula (3) and the enantimomers of the disulfide of formula (3): T-Q-L-S—S-J  (3), where -T is a moiety of formula (2) R 1 and R 2 are each individually selected from the group consisting of H and OH; a is 0 to 3; b is 0 to 3; and indicates that the chirality of the carbon atom to which it is attached is either R or S; may form inert surfaces that prevent the unwanted adsorption of proteins and cells.

1 . An alkanethiol of formula (1) and the enantimomers of the alkanethiol of formula (1):  
         HS-L-Q-T  (1),  where -L- is -(A x -B y -E z -D) w -;    each A, B, E and D are individually C(R A R A ′)—, —C(R B R B ′)—, —C(R E R E ′)—, and —C(R D R D ′)—, respectively;    each R A , R B , R E  and R D  are individually H, or any two of R A , R B , R E  and R D  together form a bond, or R A , R B , R E  and R D  together with the atoms to which they are bonded form a six-membered aromatic ring;    each R A ′, R B ′, R E ′ and R D ′ are individually H, or any two of R A ′, R B ′, R E ′ and R D ′ together form a bond, or R A ′, R B ′, R E ′ and R D ′ together with the atoms to which they are bonded form a six-membered aromatic ring;    each x, y and z are individually either 0 or 1;    w is 1 to 5;    -Q- is selected from the group consisting of                          -T is a moiety of formula (2)                          R 1  and R 2  are each individually selected from the group consisting of H and OH;    a is 0 to 3;    b is 0 to 3; and       indicates that the chirality of the carbon atom to which it is attached is either R or S.    
     
     
         2 . The alkanethiol of  claim 1 , where -T is a moiety of formula (2′)  
       
         
           
           
               
               
           
         
       
     
     
         3 . The alkanethiol of  claim 2 , where -Q- is —O— or —CH 2 — and  
     
     
         4 . A disulfide of formula (3) and the enantimomers of the disulfide of formula (3):  
         T-Q-L-S—S-J  (3),  where -L- is -(A x -B y -E z -D) w -;    each A, B, E and D are individually C(R A R A ′)—, —C(R B R B ′)—, —C(R E R E ′)—, and —C(R D R D ′)—, respectively;    each R A , R B , R E  and R D  are individually H, or any two of R A , R B , R E  and R D  together form a bond, or R A , R B , R E  and R D  together with the atoms to which they are bonded form a six-membered aromatic ring;    each R A ′, R B ′, R E ′ and R D ′ are individually H, or any two of R A ′, R B ′, R E ′ and R D ′ together form a bond, or R A ′, R B ′, R E ′ and R D ′ together with the atoms to which they are bonded form a six-membered aromatic ring;    each x, y and z are individually either 0 or 1;    w is 1 to 5;    -Q- is selected from the group consisting of                          -T is a moiety of formula (2)                          R 1  and R 2  are each individually selected from the group consisting of H and OH;    a is 0 to 3;    b is 0 to 3;       indicates that the chirality of the carbon atom to which it is attached is either R or S;    -J is selected from the group consisting of H, halogen, R, —OR, —NRR′, —C(O)R, and —C(O)OR;    R is selected from the group consisting of alkyl, alkenyl, alkynyl, aryl and heterocyclic radical; and    R′ is selected from the group consisting of H, alkyl, alkenyl, alkynyl, aryl and heterocyclic radical.    
     
     
         5 . The disulfide of  claim 4 , where -J is a moiety of formula (4):  
         -L′-Q′-T′  (4),  an alkyl having 1 to 4 carbon atoms, or —(CH 2 ) c (OCH 2 CH 2 ) n OH; and    where -L′- is -(A x -B y -E z -D) w -;    -Q′- is selected from the group consisting of                          -T′ is a moiety of formula (2)                          c is 2 to 20, and    n is 1 to 3.    
     
     
         6 . The disulfide of  claim 5 , where -J is a moiety of formula (4′):  
         -L-Q-T  (4′).  
     
     
         7 . The disulfide of  claim 6 , where -T is a moiety of formula (2′)  
       
         
           
           
               
               
           
         
       
     
     
         8 . The disulfide of  claim 7 , where -Q- is —O— or —CH 2 —.  
     
     
         9 . A substrate, comprising: 
 (i) a surface layer comprising gold, and    (ii) a plurality of moieties, on at least a portion of the surface layer,    where the moieties are alkanethiolate moieties of formula (5) and enantimomers of the alkanethiolate moieties of formula (5):      Surf-S-L-Q-T  (5);    -L- is -(A x -B y -E z -D) w -;    each A, B, E and D are individually C(R A R A ′)—, —C(R B R B ′)—, —C(R E R E ′)—, and —C(R D R D ′)—, respectively;    each R A , R B , R E  and R D  are individually H, or any two of R A , R B , R E  and R D  together form a bond, or R A , R B , R E  and R D  together with the atoms to which they are bonded form a six-membered aromatic ring;    each R A ′, R B ′, R E ′ and R D ′ are individually H, or any two of R A ′, R B ′, R E ′ and R D ′ together form a bond, or R A ′, R B ′, R E ′ and R D ′ together with the atoms to which they are bonded form a six-membered aromatic ring;    each x, y and z are individually either 0 or 1;    w is 1 to 5;    -Q- is selected from the group consisting of                          -T is a moiety of formula (2)                          R 1  and R 2  are each individually selected from the group consisting of H and OH;    a is 0 to 3;    b is 0 to 3;       indicates that the chirality of the carbon atom to which it is attached is either R or S; and    Surf designates where the moiety attaches to the surface.    
     
     
         10 . The substrate of  claim 9 , further comprising: 
 (iii) a monolayer comprising the moieties,    where the monolayer does not fail a cell patterning test at 12 days.    
     
     
         11 . The substrate of  claim 9 , further comprising: 
 (iv) a base,    where the surface layer is on the base.    
     
     
         12 . The substrate of  claim 11 , where -T is a moiety of formula (2′)  
       
         
           
           
               
               
           
         
       
     
     
         13 . The substrate of  claim 12 , where -Q- is —O— or —CH 2 —.  
     
     
         14 . The substrate of  claim 9 , where the monolayer does not fail a cell patterning test at 12 days.  
     
     
         15 . A cell chip, comprising: 
 (A) the substrate of  claim 9 , and    (B) cells, on the substrate.    
     
     
         16 . A method of making the alkanethiol of  claim 1 , comprising: 
 hydrolyzing a thioester, to form the alkanethiol of formula (1).    
     
     
         17 . A method of making the disulfide of  claim 4 , comprising: 
 oxidizing a first alkanethiol, to form the disulfide of formula (3).    
     
     
         18 . A method of making a substrate, comprising contacting a surface with the alkanethiol of  claim 1;   where the surface comprises gold.    
     
     
         19 . A method of making a substrate, comprising contacting a surface with the disulfide of  claim 4;   where the surface comprises gold.    
     
     
         20 . A method of making a cell chip, comprising: 
 contacting cells with the substrate of  claim 9.