Immune response modifier conjugates
View Patent ↗The present invention provides IRM conjugates that includes an IRM moiety and a second active moiety covalently linked to the IRM moiety in which the covalent link does not depend on UV irradiation.
1. A method of making an IRM conjugate comprising:
covalently attaching a first linker having a first functional group to an IRM compound having immunomodulatory activity, at a site on the IRM compound selected to preserve at least a portion of the immunomodulatory activity of the IRM compound, thereby forming an IRM moiety; and
allowing the IRM moiety to react with a second moiety having biological activity and a second functional group,
wherein a covalent bond is formed between the first functional group and the second functional group without use of UV irradiation, thereby forming an IRM conjugate that possesses IRM activity and the biological activity of the second moiety, and wherein the covalent bond formed by the reaction of the first functional group with the second functional group comprises a disulfide linkage, a thioether linkage, a hydrazone linkage, an oxime linkage, a urea linkage, a thiourea linkage, a hydrazine linkage, a hydroxyl amine linkage, or a nitrone linkage.
2. The method of claim 1 wherein the second moiety comprises a second linker having a second functional group attached to a compound having biological activity, at a site on the compound selected to preserve at least a portion of the biological activity of the compound.
3. The method of claim 1 wherein the second moiety is an antigenic moiety.
4. The method of claim 1 wherein the second moiety is a targeting moiety.
5. The method of claim 1 wherein the second moiety comprises a solid support that includes the second functional group.
6. The method of claim 1 , wherein the covalent bond formed by the reaction of the first functional group with the second functional group comprises a disulfide linkage or a thioether linkage, and wherein the first functional group comprises a thiol.
7. The method of claim 1 , wherein the covalent bond formed by the reaction of the first functional group with the second functional group comprises a hydrazone linkage or a hydrazine linkage, and wherein the first functional group is a 1-4-dioxo-4-hydrazino-butyl.