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(12) United States Patent (10) Patent No.: US 9,711,266 B2 Fu (45) Date of Patent: Jul.18, 2017

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(12) United States Patent (10) Patent No.: US 9,711,266 B2 Fu (45) Date of Patent: Jul.18, 2017 USOO9711266B2 (12) United States Patent (10) Patent No.: US 9,711,266 B2 Fu (45) Date of Patent: Jul.18, 2017 (54) LOW DENSITY, HIGHLY POROUS NANO (58) Field of Classification Search STRUCTURE None See application file for complete search history. (71) Applicant: NVIGEN, INC., Sunnyvale, CA (US) (72) Inventor: Aihua Fu, Sunnyvale, CA (US) (56) References Cited (73) Assignee: NVIGEN, Inc., Sunnyvale, CA (US) U.S. PATENT DOCUMENTS 2005/0244322 A1 11/2005 Chen et al. (*) Notice: Subject to any disclaimer, the term of this 2008, OO26217 A1 1/2008 Kim et al. patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. (Continued) (21) Appl. No.: 14/373,899 FOREIGN PATENT DOCUMENTS CN 101633505. A 1, 2010 (22) PCT Fed: Jan. 23, 2013 CN 101966.344 A 2, 2011 (86) PCT No.: PCT/US2O13/02281.8 (Continued) S 371 (c)(1), OTHER PUBLICATIONS (2) Date: Jul. 22, 2014 Woods, Teri. “Aerogels: Thinner, Lighter, Stronger'. http://www. (87) PCT Pub. No.: WO2O13A112643 nasa.gov/topics/technology/features/aerogels.html, Jul. 28, 2011. PCT Pub. Date: Aug. 1, 2013 (Continued) (65) Prior Publication Data Primary Examiner — Humera Sheikh US 2015/OO76392 A1 Mar. 19, 2015 Assistant Examiner — Elaine M. Vazquez Related U.S. Application Data (74) Attorney, Agent, or Firm — Jun He Law Offices P.C.; James J. Zhu (60) Provisional application No. 61/589,777, filed on Jan. 23, 2012. (57) ABSTRACT (51) Int. C. The present invention relates to nanostructures having low HOIF IMOI (2006.01) density and porous coatings that Surround or are associated B22F IM02 (2006.01) with at least one core nanoparticles. The structures are (Continued) capable of carrying or associating with at least one payload (52) U.S. C. within or on the surface of the nanostructures so that the CPC ........... HOIF I/01 (2013.01); A61K 49/0002 structures can be used in applications such as medical (2013.01); A61K 49/1887 (2013.01); B22F diagnosis or therapeutic treatment. I/02 (2013.01); (Continued) 17 Claims, 3 Drawing Sheets US 9,711.266 B2 Page 2 (51) Int. Cl. OTHER PUBLICATIONS A6 IK 49/00 (2006.01) A6 IK 49/18 (2006.01) Ben Lan Lin et al: “Microstructural Characterization and Properties C22C 29/00 (2006.01) of Silica Aerogels Doped with Nano-ITO Powder'. Advanced B22F I/OO (2006.01) Materials Research, vol. 284-286, Jul. 1, 2011 (Jul. 1, 2011), pp. A61 K 9/51 (2006.01) 662-666, XP055207003, ISSN: 1022-6680, DOI: 10.4028/www. (52) U.S. Cl. Scientific.net/AMR284-286.662. CPC ........... A6 IK 9/5115 (2013.01); B22F I/0018 Souza K C et al: "Study of mesoporous silica/magnetite systems in (2013.01); C22C 29/00 (2013.01) drug controlled release'. Journal of Materials Science: Materials in (56) References Cited Medicine, Kluwer Academic Publishers, BO, vol. 20, No. 2, Oct. 7, 2008 (Oct. 7, 2008), pp. 507-512, XPO19680 138, ISSN: 1573-4838. U.S. PATENT DOCUMENTS Wufeng Chen et al: "Self-Assembly and Embedding of Nanoparticles by In Situ Reduced Graphene for Preparation of a 3D 2010, 0008862 A1 1/2010 Fu et al. Graphene/Nanoparticle Aerogel', Advanced Materials, vol. 23, No. 2011/0229576 A1 9/2011 Trogler et al. 2012fOO77087 A1 3/2012 Cho et al. 47, Dec. 15, 2011 (Dec. 15, 2011), pp. 5679-5684. 2015,02524O7 A1* 9/2015 Fu ........................ C12O 1/6806 Ling Zhang et al. “Magnetic Hollow Spheres of Periodic 435/6.12 Mesoporous Organosilica and Fe3O4 Nanocrystals: Fabrication and Structure Control', Advanced Materials. 2008, 20, 805-809. FOREIGN PATENT DOCUMENTS Jian Liu et al. “Yolk-Shell Hybrid Materials with a Periodic CN 102145896. A 8, 2011 Mesoporous Organosilica Shell: Ideal Nanoreactors for Selective KR 10-2010-0113433 A 10, 2010 Alcohol Oxidation', Adv. Fund. Mater, 2012, 22, 591-599. KR 10-2011-0040006 A 4, 2011 WO 2009021286 A1 2, 2009 * cited by examiner U.S. Patent Jul.18, 2017 Sheet 1 of 3 US 9,711.266 B2 U.S. Patent Jul.18, 2017 Sheet 2 of 3 US 9,711.266 B2 fa) Fr-I is Wagen (ww.viswagestitch.com) product Öescription: EM &fnariparticles ess:aining m3gnetic TEM Isaicrograph airnessperols silica nar3.particies Systhesized core and silica she: component. This is for their from pi'of Cixisty . H:fe’s group. The Si:iceous strictre is Sodus of 113gnetic and fluorescent Banoparticles. The clearly abse:sable gilder TEM. J. A. Chain. So. 2 i, 133, silica structure is clearly observable inder TEM. 2444-(45. Esi i. i. TEM Sirugaph sluft irophist disc silica EMF iT graph silius's cell silic: Isa II particies by itico Rating nanopasticles gregated S Prof. Weifs:g fans giQup. organic fluorophies wišil a siliceo:3S structure in Prof. Sich These silica Fianop3rticles could be clearly observed Wiesner's grossp. the siliceous structure is clearly abservable irider sider SEM. Anai, Cheii. 2C(, 3, 4388-3993. TEM. Nana letters, 2003, 5, 13.) {} TEM ficrograph i core'shel Sianoparticles made of TEM micrograph ; silica coated PbSe nanoparticies. She silia it 3ie coe and silica sell With frescent coating is cie3sly abseilable. Fšom pf. Jackie Yi-gs group. molecules. The siliceous coating is ciearly abservable. Chemistry of Materials, 2307, 9, Si2.) From prof. Younai Xie's group. (nati letters, 26 iS3.) Figure 4 U.S. Patent Jul.18, 2017 Sheet 3 of 3 US 9,711.266 B2 EM micrograph of silica nanoparticles as synthesized (a) and incorporated with 1sultiple magnetic nanoparticies. The siliceous structure could be clearly observed under TEM. From Dr. Taeghwan Hyeon’s group. (JACS, 2010, 132, 552. Figare 4 (continued) US 9,711,266 B2 1. 2 LOW DENSITY, HIGHLY POROUS NANO In certain embodiments, the low density, porous 3-D STRUCTURE structure is highly porous. Such low density structure further refers to a structure having at least 40% to at least 99.9% CROSS-REFERENCE TO RELATED (preferably 50% to 99.9%) of empty space or porosity in the APPLICATIONS structure. In certain embodiments, at least 80% of the pores having a size of 1 nm to 500 nm in pore radius. The present application claims the benefit of U.S. Provi In certain embodiments, the low density, porous 3-D sional Patent Application No. 61/589,777, filed on Jan. 23, structure is a structure that can not be obviously observed or 2012, which is incorporated herein by reference in their is substantially invisible under transmission electron micro entirety. 10 scope, for example, even when the feature size of the low density structure is in the 10s or 100s nanometer range. BACKGROUND In certain embodiments, the low density, porous 3-D Nanoparticles provide a wide range of applications in structure is made of silicon-containing molecules (e.g., fields such as molecular imaging, early stage diagnosis and 15 silanes, organosilanes, alkoxysilanes, silicates and deriva targeted therapy. It is challenging but desirable to design and tives thereof). For example, the silicon-containing mol prepare nanoparticles that are capable of incorporating or ecules can be amino-propyl-trimethoxysilane, mercapto carrying a large amount of payloads and performing a propyl-trimethoxysilane, carboxyl-propyl-trimethoxysilane, plurality of functions in the same nanoparticles. Therefore, amino-propyl-triethoxysilane, mercapto-propyl-triethoxysi there are needs to continue to develop Such nanoparticles. lane, carboxyl-propyl-triethoxysilane, Bis-3-(triethoxysi lyl) propyl-tetrasulfide, Bis-3-(triethoxysilyl) propyl-dis SUMMARY OF THE INVENTION ulfide, aminopropyltriethoxysilane, N-2-(aminoethyl)-3- aminopropyltrimethoxysilane, Vinyltrimethoxysilane, One aspect of the present disclosure relates to a nano Vinyl-tris(2-methoxyethoxy) silane, 3-methacryloxypropyl structure comprising at least one core nanoparticle embed 25 trimethoxy silane, 2-(3.4-epoxycyclohexy)-ethyl trimethox ded in or coated with a low density porous 3-D structure or ysilane, 3-glycidoxy-propyltriethoxysilane, 3-isocyanato coating, which is capable of carrying or associating with at propyltriethoxysilane, 3-cyanatopropyltriethoxysilane, and least one payload within or on the Surface of the nanostruc Sodium silicates. ture. In certain embodiments, the low density, porous 3-D In certain embodiments, the core nanoparticle comprises 30 structure is associated with the core nanoparticle via intra a nanoparticle or a cluster of nanoparticles. A single core molecular interaction (e.g. covalent bonds, metallic bonds nanoparticle may comprise a plurality or a cluster of mini and/or ionic bonding) or inter-molecular interaction (e.g. nanoparticles. The nanoparticles in the cluster may be made hydrogen bond, and/or non covalent bonds). by the same composition, or different compositions. In certain embodiments, the low density, porous 3-D In certain embodiments, the core nanoparticle includes, 35 structure is a stable crosslinked coating with thickness for example, a Superparamagnetic iron oxide (SPIO) nano ranging from 1 nm to 1000 nm (e.g. from 1 nm to 500 nm). particle, or a non-SPIO nanoparticle. The non-SPIO nano In certain embodiments, the thickness of the low density, particles include, for example, metallic nanoparticles (e.g., porous 3-D structure is controllable, so is the number of gold or silver nanoparticles), a metal oxide nanoparticle, payloads that could be carried. As a result, the nanostruc semiconductor nanoparticle (e.g., quantum dots with indi 40 tures when systematically applied as injectable agents into vidual or multiple components such as CdSe/ZnS, doped the blood stream of a living Subject can accumulate at a heavy metal free quantum dots or other semiconductor disease region, Such as a tumor or inflammation site. In quantum dots); polymeric nanoparticles (e.g., particles made certain embodiments, the nanostructure is capable of carry of one or a combination of PLGA (poly(lactic-co-glycolic ing or being associated with one or more payloads.
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