# US 10,864,169 B2 · Conjugated polymer nanoparticles and manufacturing method thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,864,169 B2 - Document ID: US10864169B2 - Status: Granted - Kind: B2 - Application number: 15/505,036 - Filed: 2015-03-19 - Published: 2017-09-21 - Granted: 2020-12-15 - Earliest claimed: 2014-08-20 - Assignees: Industry-Academic Cooperation Foundation, Yonsei University - Applicants: Industry-Academic Cooperation Foundation, Yonsei University - Inventors: Jae Moon Yang; Jung Hyun Kim; Jeong Hun Kim; Yoo Chan Hong; Won Seok Cho; Seung Yeon Hwang; Jin Suck Suh - Web page: https://patentgrep.com/patent/US10864169B2 ## CPC - A61K 9/5146: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides} - A61K 9/5123: {Organic compounds, e.g. fats, sugars} - A61K 9/513: {Organic macromolecular compounds; Dendrimers} - A61K 9/5192: {Processes} - A61K 31/704: attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin {(digitoxin A61K31/7048)} - A61K 41/0028: {Disruption, e.g. by heat or ultrasounds, sonophysical or sonochemical activation, e.g. thermosensitive or heat-sensitive liposomes, disruption of calculi with a medicinal preparation and ultrasounds} - A61K 41/0052: {Thermotherapy; Hyperthermia; Magnetic induction; Induction heating therapy} - A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence) - A61K 49/00: Preparations for testing in vivo - A61K 49/0054: {Macromolecular compounds, i.e. oligomers, polymers, dendrimers} - A61K 49/0093: {Nanoparticle, nanocapsule, nanobubble, nanosphere, nanobead, i.e. having a size or diameter smaller than 1 micrometer, e.g. polymeric nanoparticle} - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract Disclosed are conjugated polymer nanoparticles and a method of producing the same. The conjugated polymer nanoparticles include a conjugated polymer, fatty acid and an amphiphile polymer. The conjugated polymer nanoparticles can be doped even under a neutral environment, thus exhibiting high electrical conductivity and exerting absorbance properties in the near-infrared band even under a neutral environment such as in vivo. ## Claims ### Claim 1 Conjugated polymer nanoparticles for photothermal therapy comprising: a core consisting of a mixture of a conjugated polymer and a fatty acid, and a pharmaceutically active ingredient; and a shell surrounding the core and comprising an amphiphile polymer, wherein: the fatty acid is selected from the group consisting of oleic acid, capric acid, caprylic acid, palmitic acid, lauric acid, myristic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid and combinations thereof, the conjugated polymer is capable of being doped in the presence of HCI having a lower concentration than 10−3 M, the fatty acid is a phase change material which is present in a solid phase during production of the conjugated polymer nanoparticles and is adapted to be melted by heat emitted from the conjugated polymer absorbing light, and the conjugated polymer of the conjugated polymer nanoparticles is capable of being doped at pH 1 to 8 with a dopant. ### Claim 2 (depends on 1) The conjugated polymer nanoparticles for photothermal therapy according to claim 1, wherein the conjugated polymer nanoparticles comprise 1 to 1,000 parts by weight of the fatty acid and 1 to 1,000 parts by weight of the amphiphile polymer, with respect to 100 parts by weight of the conjugated polymer. ### Claim 3 (depends on 1) The conjugated polymer nanoparticles for photothermal therapy according to claim 1, wherein the amphiphile polymer comprises any one selected from the group consisting of a cationic surfactant, an anionic surfactant, an amphoteric surfactant, a nonionic surfactant and a mixture thereof. ### Claim 4 (depends on 3) The conjugated polymer nanoparticles for photothermal therapy according to claim 3, wherein the amphiphile polymer comprises any one selected from the group consisting of sodium cholate hydrate, n-octyl glucoside, octyl thioglycoside, N-octanoyl-N-methylglucamine, N-nonanoyl-N-methylglucamine, quillaja bark-derived saponin, polyoxyethylene sorbitan monolaurate, sodium dodecyl sulfate, tetramethylammonium hydroxide solution, hexadecyltrimethylammonium bromide (CTAB), didodecyldimethylammonium bromide (DMAB), N,N-bis(3-D-glucoamidopropyl)deoxy -cholamide (deoxy-BIGCHAP), N,N-bis(3-D-glucoamidopropyl)cholamide (BIGCHAP), polyvinyl alcohol, polyethylene glycol dodecyl ether, N-decanoyl-N-methylglucamine, nonylphenyl polyethylene glycol, Polysorbate 80, cyclohexylmethyl-β-D-maltoside (Cymal-1), 2-cyclohexylethyl-β-D-maltoside (Cymal-2), 5-cyclohexylpentyl-β-D-maltoside (Cymal-5), 6-cyclohexylhexyl-β-D-maltoside (Cymal-6), digitonin, decyl-β-D-maltopyranoside, lauryl-β-D-maltoside (DDM), n-hexadecyl-β-D-maltoside, undecyl-β-D-maltoside, decyl-β-D-1-thiomaltopyranoside, decyl-β-D-1-thioglucopyranoside, dimethyldecylphosphine oxide, dodecyldimethylphosphine oxide and a mixture thereof. ### Claim 5 (depends on 1) The conjugated polymer nanoparticles for photothermal therapy according to claim 1, wherein the conjugated polymer comprises any one selected from the group consisting of polyacetylene, polyaniline, polypyrrole, polythiophene, poly(1,4-phenylenevinylene), poly(1,4-phenylene sulfide), poly(fluorenyleneethynylene), a derivative thereof and a mixture thereof. ### Claim 6 (depends on 1) The conjugated polymer nanoparticles for photothermal therapy according to claim 1, wherein the conjugated polymer nanoparticles comprise 0.1 to 100 parts by weight of the pharmaceutically active ingredient, with respect to 100 parts by weight of the conjugated polymer. ### Claim 7 (depends on 1) The conjugated polymer nanoparticles for photothermal therapy according to claim 1, wherein the pharmaceutically active ingredient comprises any one selected from the group consisting of anticancer agents, antibiotics, hormones, hormone antagonists, interleukins, interferons, growth factors, tumor necrosis factors, endotoxins, lymphotoxins, urokinase, streptokinase, tissue plasminogen activators, protease inhibitors, alkylphosphocholine, radioisotope-labeled molecules, cardiovascular drugs, gastrointestinal drugs and neurological drugs. ### Claim 8 (depends on 1) The conjugated polymer nanoparticles for photothermal therapy according to claim 1, wherein the conjugated polymer nanoparticles have a diameter of 1 to 500 nm. ### Claim 9 A method of producing conjugated polymer nanoparticles for photothermal therapy comprising: dissolving a conjugated polymer and fatty acid in a solvent to prepare a first mix solution; mixing the first mix solution with a solution containing an amphiphile polymer to prepare a second mix solution; and conducting reaction of the second mix solution, wherein the conjugated polymer nanoparticles comprise a core consisting of the mixture of the conjugated polymer and the fatty acid, and a pharmaceutically active ingredient; and a shell surrounding the core and comprising the amphiphile polymer, and wherein: the fatty acid is selected from the group consisting of oleic acid, capric acid, caprylic acid, palmitic acid, lauric acid, myristic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, and combinations thereof, the conjugated polymer is capable of being doped in the presence of HCI having a lower concentration than 10−3 M, the fatty acid is a phase change material which is present in a solid phase during the production of the conjugated polymer nanoparticles and can be melted by heat emitted from the conjugated polymer absorbing light, and the conjugated polymer of the conjugated polymer nanoparticles is capable of being doped at pH 1 to 8 with a dopant. ### Claim 10 (depends on 9) The method according to claim 9, wherein the preparing the first mix solution comprises further adding a pharmaceutically active ingredient. ### Claim 11 (depends on 9) The method according to claim 9, wherein the solvent comprises any one selected from the group consisting of N-methyl-2-pyrrolidone, acetone, acetonitrile, carbon tetrachloride, chloroform, cyclohexane, 1,2-dichloroethane, dichloromethane, diethyl ether, dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, heptane, hexane, methanol, methyl tert-butyl ether, pentane, 1-propanol, 2-propanol, tetrahydrofuran, toluene, 2,2,4-trimethylpentane, water and a mixture thereof. ### Claim 12 (depends on 9) The method according to claim 9, wherein the reaction of the second mix solution is conducted by stirring the second mix solution at a temperature lower than or equal to a melting point of the fatty acid.