N-sulfonylaminocarbonyl containing compounds
View Patent ↗Compounds having two reactive functional groups are described that can be used to provide a connector group between a substrate and an amine-containing material. The first reactive functional group can be used to provide attachment to a surface of a substrate. The second reactive functional group is a N-sulfonylaminocarbonyl group that can be reacted with an amine-containing material, particularly a primary aliphatic amine, to form a carbonylimino-containing connector group. The invention also provides articles and methods for immobilizing amine-containing materials to a substrate.
1. A compound of Formula Ia:
wherein
R 5 is hydrogen, alkyl, or aryl;
L 1 is oxy, —NR 4 —, or —C(R 4 ) 2 —, wherein R 4 is hydrogen, alkyl, or aryl;
Z 1 is an alkyl, aryl, or —(CO)R a wherein R a together with R 1 and groups to which they are attached form a four to eight membered heterocyclic or heterobicyclic group having a nitrogen heteroatom and a sulfur heteroatom, wherein said heterocyclic or heterobicyclic group can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
R 1 is an alkyl, fluoroalkyl, chloroalkyl, aryl, NR b R c wherein R b and R c are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered cyclic group, or R 1 together with R a and the groups to which they are attached form the four to eight membered heterocyclic or heterobicyclic group that can be fused to the optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
Y 2 is a single bond or a divalent group selected from an alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NR 4 —, or combinations thereof, wherein R 4 is hydrogen, alkyl, or aryl; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
2. The compound of claim 1 , wherein the compound has a formula
wherein
D is oxygen, sulfur, or NH;
m is an integer of 1 to 200;
n is an integer of 1 to 12;
k is an integer of 2 to 4; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
3. The compound of claim 1 , where the compound is of formula
wherein said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
4. The compound of claim 1 , wherein the compound is
wherein said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
5. An article comprising:
a substrate;
a substrate-attached tethering group comprising a reaction product of a complementary functional group G on a surface of the substrate with an ethylenically unsaturated group of a compound of Formula Ia;
wherein
R 5 is hydrogen, alkyl, or aryl;
L 1 is oxy, —NR 4 —, or —C(R 4 ) 2 —, wherein R 4 is hydrogen, alkyl, or aryl;
Z 1 is an alkyl, aryl, or —(CO)R a wherein R a together with R 1 and groups to which they are attached form a four to eight membered heterocyclic or heterobicyclic group having a nitrogen heteroatom and a sulfur heteroatom, wherein said heterocyclic or heterobicyclic group can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
R 1 is an alkyl, fluoroalkyl, chloroalkyl, aryl, NR b R c wherein R b and R c are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered cyclic group, or R 1 together with R a and the groups to which they are attached form the four to eight membered heterocyclic or heterobicyclic group that can be fused to the optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
Y 2 is a single bond or a divalent group selected from an alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NR 4 —, or combinations thereof, wherein R 4 is hydrogen, alkyl, or aryl; and
said tethering group is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
6. The article of claim 5 , wherein the compound has a formula
wherein
D is oxygen, sulfur, or NH;
m is an integer of 1 to 200;
n is an integer of 1 to 12;
k is an integer of 2 to 4; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
7. The article of claim 5 , wherein the compound has a formula
wherein said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
8. The article of claim 5 , wherein the substrate comprises a polymeric material.
9. The article of claim 5 , wherein the substrate comprises a polyimide or polyester film.
10. The article of claim 5 , wherein the substrate is multilayered and has an outer layer comprising gold.
11. The article of claim 5 , wherein the substrate is multilayered and has an outer layer comprising diamond-like glass.
12. The article of claim 5 , wherein the substrate is a multilayer substrate comprising;
a support layer comprising polyimide or polyester;
an outer layer comprising diamond-like glass;
and a layer of diamond-like glass positioned between the support layer and the outer layer.
13. The article of claim 5 , wherein the substrate is in the form of a bead.
14. A method of immobilizing an amine-containing material to a substrate, said method comprising:
selecting a compound of Formula Ia,
the compound having an ethylenically unsaturated group, wherein
R 5 is hydrogen, alkyl, or aryl;
L 1 is oxy, —NR 4 —, or —C(R 4 ) 2 —, wherein R 4 is hydrogen, alkyl, or aryl;
Z 1 is an alkyl, aryl, or —(CO)R a wherein R a together with R 1 and groups to which they are attached form a four to eight membered heterocyclic or heterobicyclic group having a nitrogen heteroatom and a sulfur heteroatom, wherein said heterocyclic or heterobicyclic group can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
R 1 is an alkyl, fluoroalkyl, chloroalkyl, aryl, NR b R c wherein R b and R c are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered cyclic group, or R 1 together with R a and the groups to which they are attached form the four to eight membered heterocyclic or heterobicyclic group that can be fused to the optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
Y 2 is a single bond or a divalent group selected from an alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NR 4 —, or combinations thereof, wherein R 4 is hydrogen, alkyl, or aryl; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof;
providing a substrate having a complementary functional group capable of reacting with the ethylenically unsaturated group;
preparing a substrate-attached tethering group by reacting the ethylenically unsaturated group with the complementary functional group on the substrate resulting in an ionic bond, covalent bond, or combination thereof; and
reacting an amine-containing material with a N-sulfonylaminocarbonyl group of the substrate-attached tethering group to form a carbonylimino-containing connector group between the substrate and the amine-containing material.
15. The method of claim 14 , wherein the amine-containing material is an amine-containing analyte, an amino acid, peptide, DNA, RNA, protein, enzyme, organelle, immunoglobulin, or fragment thereof.
16. The method of claim 14 , wherein the amine-containing material is an antibody and the antibody is further bound to an antigen.
17. The method of claim 14 , wherein the amine-containing material is an antigen and the antigen is further bound to an antibody.
18. The article of claim 14 , wherein the amine-containing material is an immunoglobulin.
19. The method of claim 14 , wherein the amine-containing material is further bound to a bacterium.
20. The method of 19 , wherein the bacterium is Staphylococcus aureus.
21. The method of claim 14 , wherein the compound is of formula
wherein
D is oxygen, sulfur, or NH;
m is an integer of 1 to 200;
n is an integer of 1 to 12;
k is an integer of 2 to 4; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
22. The method of claim 14 , wherein the compound has a formula
wherein said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.