Multifunctional small molecules

• US 8,912,323 B2
• Filed: 09/30/2010
• Issued: 12/16/2014
• Est. Priority Date: 10/30/2009
• Status: Expired due to Fees

• Current Assignee: Board of Regents of the University of Michigan (University of Michigan)
• Original Assignee: Board of Regents of the University of Michigan (University of Michigan)
• Inventors: Baker, James R. Jr., Zong, Hong, Thomas, Thommey P.
• Primary Examiner(s): Balasubramanian, Venkataraman
• Application Number:
  US13/504,046
• Publication Number:
  US 20120259114A1
• Time in Patent Office: 1,538 Days
• Field of Search: 544/180, 544/196, 544/204, 544/215, 514/241, 514/245
• US Class Current: 544/180
• CPC Class Codes: A61K 47/551 one of the codrug's components being a vitamin, e.g. niacinamide, vitamin B3, cobalamin, vitamin B12, folate, vitamin A or retinoic acid
• CPC Class Codes: A61K 47/595 Polyamides, e.g. nylon polyamino acids A61K47/62
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C08G 83/003 Dendrimers

Abstract

The present invention relates to dendrimer synthesis. Specifically, the present invention relates to triazine scaffolds capable of click chemistry for one-step synthesis of functionalized dendrimers, and methods of making and using the same.

Claims

1. A composition comprising a PAMAM dendrimer conjugated with a triazine compound, wherein said triazine compound is selected from the group consisting of

2. The composition of claim 1, wherein said PAMAM dendrimer is conjugated with said triazine compound via a 3-azido-coumarine linkage agent.

3. The composition of claim 1, wherein said triazine compound is conjugated with one or more ligands.

4. The composition of claim 3, wherein said one or more ligands are independently selected from the group consisting of a therapeutic agent, a targeting agent, an imaging agent, and a trigger agent.

5. The composition of claim 3, wherein said one or more ligands are methotrexate, folic acid, and 3-azido-coumarine.

6. A method of synthesizing a functionalized dendrimer, said method comprising:

a) providing an alkyne-modified PAMAM dendrimer and a triazine compound, wherein said triazine compound is selected from the group consisting of

7. The method of claim 6, wherein conjugating of said alkyne-modified PAMAM dendrimer with said triazine compound occurs via a click chemistry reaction.

8. The method of claim 6, wherein said PAMAM dendrimer is conjugated with said triazine compound via a 3-azido-coumarine linkage agent.

9. The method of claim 6, further comprising step c) conjugating one or more ligands with said triazine compound.

10. The method of claim 9, wherein said one or more ligands are selected from the group consisting of a therapeutic agent, a targeting agent, an imaging agent, and a trigger agent.

11. The method of claim 9, wherein said one or more ligands are methotrexate and folic acid.