Synthesis of hyperbranched amphiphilic polyester and theranostic nanoparticles thereof

Patent metadata

Field	Value
Publication number	US-2016256402-A1
Application number	US-201615049823-A
Country	US
Kind code	A1
Filing date	Feb 22, 2016
Priority date	Apr 2, 2008
Publication date	Sep 8, 2016
Grant date	—

Abstract

A method of making a hyperbranched amphiphilic polyester compound includes drying under vacuum a mixture of 2-(4-hydroxybutyl)-malonic acid and p-toluene sulphonic acid as catalyst. The vacuum is then released with a dry inert gas after drying. The dried mixture is heated under the inert gas at a temperature sufficient for polymerization. The inert gas is evacuated while continuing to heat the mixture. The formed polymer is then dissolved in dimethylformamide and precipitated out by adding methanol. Modifications of the method yield nanoparticles of polyesters having properties suited for coencapsulating fluorescent dyes together with therapeutic drugs, resulting in theranostic nanoparticles, that is, nanoparticles useful in both therapeutic treatments and diagnostic methods.

First claim

1 - 23 . (canceled)

24 . A polymer comprising the repeating unit:

25 . A polymeric nanoparticle comprising the polymer of claim 24 .

26 . The polymeric nanoparticle of claim 25 , wherein the polymeric nanoparticle is biodegradable.

27 . The polymeric nanoparticle of claim 25 , having one or more internal hydrophobic pockets and a hydrophilic outer surface.

28 . The polymeric nanoparticle of claim 25 , having an average diameter of 115±25 nm.

29 . The polymeric nanoparticle of claim 25 , being spherical in shape.

30 . The polymeric nanoparticle of claim 25 , having a positive zeta potential.

31 . The polymeric nanoparticle of claim 25 , further comprising a hydrophobic near-infrared fluorescent dye encapsulated therein.

32 . The polymeric nanoparticle of claim 31 , wherein the dye is selected from the group consisting of DiI, DiR, DiD, and combinations thereof.

33 . The polymeric nanoparticle of claim 25 , further comprising one or more therapeutic drugs encapsulated therein.

34 . The polymeric nanoparticle of claim 33 , wherein the therapeutic drug comprises an anti-cancer drug.

35 . The polymeric nanoparticle of claim 33 , wherein the therapeutic drug comprises azidothymidine.

36 . The polymeric nanoparticle of claim 33 , wherein the therapeutic drug comprises paclitaxel.

37 . The polymeric nanoparticle of claim 33 , further comprising a fluorescent dye co-encapsulated with said therapeutic drug.

38 . The polymeric nanoparticle of claim 25 , further comprising a targeting ligand.

39 . The polymeric nanoparticle of claim 25 , further comprising folate.

40 . An aqueous suspension of the polymeric nanoparticle of claim 25 .

41 . The aqueous suspension of claim 40 , further comprising a hydrophobic near-infrared fluorescent dye.

42 . The aqueous suspension of claim 40 , further comprising a therapeutic drug.

43 . The aqueous suspension of claim 40 , further comprising a hydrophobic near-infrared fluorescent dye and a therapeutic drug.

44 . A method of functionalizing a nanoparticle, comprising: contacting the nanoparticle of claim 33 with an azide.

Assignees

• Univ Central Florida Res Found Inc

Inventors

• Perez J Manuel
• Santra Santimukul

Classifications

• C08G83/005 Primary

  Hyperbranched macromolecules · CPC title

• A61K49/0032

  Methine dyes, e.g. cyanine dyes · CPC title

• C08G83/006

  After treatment of hyperbranched macromolecules · CPC title

• A61K31/7072

  having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine · CPC title

• A61K9/5138 Primary

  obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates · CPC title