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(12) Patent Application Publication (10) Pub. No.: US 2006/0083781 A1 Shastri Et Al US 20060083.781A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2006/0083781 A1 Shastri et al. (43) Pub. Date: Apr. 20, 2006 (54) FUNCTIONALIZED SOLID LIPID Publication Classification NANOPARTICLES AND METHODS OF MAKING AND USING SAME (51) Int. Cl. A 6LX 9/27 (2006.01) (76) Inventors: V. Prasad Shastri, Nashville, TN (US); (52) U.S. Cl. ............................................ 424/450; 977/907 Eric Sussman, Seattle, WA (US); Ashwath Jayagopal, Nashville, TN (57) ABSTRACT (US) In one aspect, the invention relates to functionalized solid lipid nanoparticles comprising a neutral lipid and a first Correspondence Address: functionalized polymer comprising at least one ionic or NEEDLE & ROSENBERG, PC. ionizable moiety and methods for providing same. In a SUTE 1 OOO further aspect, the invention relates to tumor targeting thera 999 PEACHTREE STREET peutic systems, multimodal diagnostic therapeutic systems, ATLANTA, GA 30309-3915 (US) thermoresponsive payload delivery systems, magnetic driven targeting systems, therapeutic diagnostic systems, (21) Appl. No.: 11/251,109 stabilized ink compositions, and cosmetic formulations comprising the Solid lipid nanoparticles of the invention. In (22) Filed: Oct. 14, 2005 a further aspect, the invention relates to methods of deliv ering at least one biologically active agent, pharmaceutically Related U.S. Application Data active agent, magnetically active agent, or imaging agent across the blood-brain barrier, across a cellular lipid bilayer (60) Provisional application No. 60/618,962, filed on Oct. and into a cell, and to a subcellualr structure. This abstract 14, 2004. Provisional application No. 60/658,520, is intended as a scanning tool for purposes of searching in filed on Mar. 3, 2005. Provisional application No. the particular art and is not intended to be limiting of the 60/722,132, filed on Sep. 30, 2005. present invention. Patent Application Publication Apr. 20, 2006 Sheet 1 of 27 US 2006/0083.781 A1 SLN Prepared using binary solvent systems of 1000 varying polarity 900 E S. O N Polarity (SPP) FIGURE 1 Patent Application Publication Apr. 20, 2006 Sheet 2 of 27 US 2006/0083.781 A1 Lipid-encapsulated quantum dot diameter as a function of n-methyl pyrrollidone volume fraction d) 1. S. (v. Y. O O 100 2 is S 5 O G 5 O 50 60 70 80 90 100 NMP volume 96, organic phase FIGURE 2 Patent Application Publication Apr. 20, 2006 Sheet 3 of 27 US 2006/0083.781 A1 Control of SLNSize Using Binary Solvent Systems of Varying Polarity 85 86 87 88 89 90 91 92 93 94 95 96 97 Polarity (SPP) FIGURE 3 Patent Application Publication Apr. 20, 2006 Sheet 4 of 27 US 2006/0083.781 A1 FIGURE 4 Patent Application Publication Apr. 20, 2006 Sheet 5 of 27 US 2006/0083.781 A1 FIGURES Patent Application Publication Apr. 20, 2006 Sheet 6 of 27 US 2006/0083.781 A1 FIGURE 6 Patent Application Publication Apr. 20, 2006 Sheet 7 of 27 US 2006/0083.781 A1 FIGURE 7 Patent Application Publication Apr. 20, 2006 Sheet 8 of 27 US 2006/0083.781 A1 FIGURE 8 Patent Application Publication Apr. 20, 2006 Sheet 9 of 27 US 2006/0083.781 A1 FIGURE 9 Patent Application Publication Apr. 20, 2006 Sheet 10 of 27 US 2006/0083.781 A1 CONTROL INCUBATED WITH SLN-QD 10 MINUTES FLUORESCENCE INTENSITY (A.U.) FIGURE 10 Patent Application Publication Apr. 20, 2006 Sheet 11 of 27 US 2006/0083.781 A1 100 80. i f . w - . r 1OS. 3 * O 1 O :: . * v -- FIGURE 11 Patent Application Publication Apr. 20, 2006 Sheet 12 of 27 US 2006/0083.781 A1 Poly-L-lysine is Adsorbed to the 4000 SLN-QD Surface 3500 2 O O O 480 505 530 555 58O 605 630 655 68O Emission Wavelength (nm) FIGURE 12 Patent Application Publication Apr. 20, 2006 Sheet 13 of 27 US 2006/0083.781 A1 Zeta Potential of SLN-QD-PSS 1 5 1 O 5 s 5 O s FIGURE 13 Patent Application Publication Apr. 20, 2006 Sheet 14 of 27 US 2006/0083.781 A1 bOMine enCO heal Celayer in SOated Ge. FIGURE 14 Patent Application Publication Apr. 20, 2006 Sheet 15 of 27 US 2006/0083.781 A1 Albumin transport across bovine aortic endothelial cell monolayer 2 9. 8 O E W IX FIGURE 15 Patent Application Publication Apr. 20, 2006 Sheet 16 of 27 US 2006/0083.781 A1 6-Coumarin transport across bovine aortic endothelial cell monolayer VII IX FIGURE 16 Patent Application Publication Apr. 20, 2006 Sheet 17 of 27 US 2006/0083.781 A1 FIGURE 17 Patent Application Publication Apr. 20, 2006 Sheet 18 of 27 US 2006/0083.781 A1 FIGURE 18 Patent Application Publication Apr. 20, 2006 Sheet 19 of 27 US 2006/0083.781 A1 FIGURE 19 Patent Application Publication Apr. 20, 2006 Sheet 20 of 27 US 2006/0083.781 A1 rivativ s Direct as: 175000x series is FIGURE 20 Patent Application Publication Apr. 20, 2006 Sheet 21 of 27 US 2006/0083.781 A1 1 O V {0 Ze N taP \ N ot -- en Anionic Surface Cationic Surface tia - Chemistry Chemistry FIGURE 21 Patent Application Publication Apr. 20, 2006 Sheet 22 of 27 US 2006/0083.781 A1 FIGURE 22 Patent Application Publication Apr. 20, 2006 Sheet 23 of 27 US 2006/0083.781 A1 FIGURE 23 Patent Application Publication Apr. 20, 2006 Sheet 24 of 27 US 2006/0083.781 A1 FIGURE 24 Patent Application Publication Apr. 20, 2006 Sheet 25 of 27 US 2006/0083.781 A1 FIGURE 25 Patent Application Publication Apr. 20, 2006 Sheet 26 of 27 US 2006/0083.781 A1 FIGURE 26 Patent Application Publication Apr. 20, 2006 Sheet 27 of 27 US 2006/0083.781 A1 FIGURE 27 US 2006/0083.781 A1 Apr. 20, 2006 FUNCTIONALIZED SOLID LIPID exterior, and a diameter, wherein at least a portion of the NANOPARTICLES AND METHODS OF MAKING polyether is at the exterior of the solid lipid nanoparticle; and AND USING SAME wherein the diameter of the solid lipid nanoparticle is from about 10 nm to about 1,000 nm. In a further aspect, the solid PRIORITY CLAIM lipid nanoparticle can further comprise at least one of a 0001. This application claims the benefit of U.S. appli biologically active agent, a pharmaceutically active agent, a cation Ser. No. 60/618,962, filed Oct. 14, 2004; U.S. Appli magnetically active agent, or an imaging agent, or a mixture cation No. 60/658,520, filed Mar. 3, 2005; and U.S. Appli thereof. cation No. 60/722,132, filed Sep. 30, 2005, which are all 0006. In a further aspect, the invention relates to a hereby incorporated herein by reference in their entireties. functionalized quantum dot comprising one or more quan tum dots encapsulated within the Solid lipid nanoparticle of BACKGROUND the invention. In a further aspect, the first functionalized 0002 Solid lipid nanoparticles (SLN) were developed at layer of the functionalized quantum dot can further comprise the beginning of the 1990s as an alternative carrier system at least one cysteine-rich protein, at least one metallothio to emulsions, liposomes, and polymeric nanoparticles. SLN nein-rich protein, or a mixture thereof. can provide advantages including stabilization of incorpo 0007. In a further aspect, the invention relates to tumor rated compounds, controlled release, occlusivity, and film targeting therapeutic systems comprising the Solid lipid formation on skin, including in vivo effects on the skin. SLN nanoparticle of the invention and a pharmaceutically active are conventionally prepared by a melting/solidification pro agent encapsulated within the solid lipid nanoparticles; cess, wherein the lipid is first melted, dispersed in water and wherein the biologically active agent comprises at least one then cooled to solidify the lipid particles. Alternatively, SLN enzyme. are conventionally produced using an emulsion process akin to the formation of polymeric microparticles, wherein the 0008. In a further aspect, the invention relates to multi lipids are dissolved in a solvent, emulsified, and then dis modal diagnostic therapeutic systems comprising at least persed in an aqueous Solution containing an emulsifying one solid lipid nanoparticle of the invention. agent to harden the solid lipid nanoparticles. The role of the 0009. In a further aspect, the invention relates to multi emulsifying agent is to stabilize the SLN; however, it also modal diagnostic therapeutic systems comprising a lipo precludes further functionalization of the SLN. SLN are some comprising at least one solid lipid nanoparticle of the generally known to those of skill in the art and may be invention encapsulated within the liposome, optionally fur obtained by conventional methods as described in, for ther comprising a biologically active agent, a pharmaceuti example, M. R. Gasco, Nanoparticelle Lipidiche Solide cally active agent, a magnetically active agent, imaging Quali Sistemi Terapeutici Colloidali, NCF nr. 7, 1996, pg agent, or a mixture thereof encapsulated within the lipo 71-73; Kozariara et al., In-situ Blood-Brain Barrier Trans SO. port of Nanoparticles, Pharmaceutical Research, Vol. 20, no. 11, p. 1772 (2003); and Lockman, et al., Brain Uptake of 0010. In a further aspect, the invention relates to multi Thiamine-Coated Nanoparticles, Journal of Controlled modal diagnostic therapeutic systems comprising a micro Release, 93 (2003) 271-282. sphere comprising at least one solid lipid nanoparticle of the invention encapsulated within the microsphere, optionally 0003. However, SLN prepared by conventional means further comprising a delivery package. Such as a biologically generally require the use of Surfactants or emulsifiers, typi active agent, a pharmaceutically active agent, a magnetically cally fail to achieve stable aqueous Suspensions, and/or fail active agent, imaging agent, or a mixture thereof encapsu to provide satisfactory surface functionalization.
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