Surface modifying composition

• US 20050255582A1
• Filed: 05/06/2005
• Published: 11/17/2005
• Est. Priority Date: 10/11/2000
• Status: Abandoned Application

• Current Assignee: University of Chicago
• Original Assignee: ARCH Development Corporation (University of Chicago)
• Inventors: Mrksich, Milan, Luk, Yan-Yeung
• Application Number:
  US11/124,022
• Publication Number:
  US 20050255582A1
• Time in Patent Office: Days
• US Class Current: 435/287.200
• CPC Class Codes: B05D 1/185 applying monomolecular layers B05D1/204 takes precedence
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C07C 323/12 the carbon skeleton being acyclic and saturated

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)
R¹ and R² 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.

Claims

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_AR_A′

)—

, —

C(R_BR_B′

)—

, —

C(R_ER_E′

)—

, and —

C(R_DR_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)

R¹ and R² 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 —

CH₂— and

16. A method of making the alkanethiol of claim 1, comprising:

hydrolyzing a thioester, to form the alkanethiol of formula (1).

18. A method of making a substrate, comprising contacting a surface with the alkanethiol of claim 1;

where the surface comprises gold.

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_AR_A′

)—

, —

C(R_BR_B′

)—

, —

C(R_ER_E′

)—

, and —

C(R_DR_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)

R¹ and R² 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 —

(CH₂)_c(OCH₂CH₂)_nOH; 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 —

CH₂—

.

17. A method of making the disulfide of claim 4, comprising:

oxidizing a first alkanethiol, to form the disulfide of formula (3).

19. A method of making a substrate, comprising contacting a surface with the disulfide of claim 4;

where the surface comprises gold.

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_AR_A′

)—

, —

C(R_BR_B′

)—

, —

C(R_ER_E′

)—

, and —

C(R_DR_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)

R¹ and R² 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 —

CH₂—

.

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.

20. A method of making a cell chip, comprising:

contacting cells with the substrate of claim 9.