# US 12,599,677 B2 · Targeted PH sensitive liposomes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,599,677 B2 - Document ID: US12599677B2 - Status: Granted - Kind: B2 - Application number: 18/030,231 - Filed: 2021-10-04 - Published: 2023-11-23 - Granted: 2026-04-14 - Earliest claimed: 2020-10-05 - Assignees: Northwestern University - Applicants: Northwestern University - Inventors: Leo I. Gordon; Dong-Hyun Kim; Shuo Yang; Wooram Park; Taehoon Sim - Web page: https://patentgrep.com/patent/US12599677B2 ## CPC - A61K 9/1271: Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers (liposomes as conjugates {A61K47/6911}) - A61K 47/6911: {the form being a liposome} - A61K 31/365: Lactones - A61K 47/62: the modifying agent being a protein, peptide or polyamino acid - A61P 35/00: Antineoplastic agents - C07K 14/47: from mammals - Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change - 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) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00) - Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE ## Abstract Disclosed herein are synthetic nanoparticles, pharmaceutical compositions, kits, or methods for treating and/or preventing cancer. In some embodiments, the synthetic nanoparticles and/or pharmaceutical compositions comprises a pH sensitive liposome, an apolipoprotein, and andrographolide or derivative thereof. In some embodiments, the synthetic nanoparticles are delivered to a subject for treatment of cancer. In some embodiments, the cancer is T-cell lymphoma or B-cell lymphoma. ## Claims ### Claim 1 A synthetic nanoparticle comprising: a pH sensitive liposome comprising a lipid layer comprising at least one pH sensitive (a) lipid; (b) an apolipoprotein in contact with the lipid layer; and (c) a drug having a low water solubility encapsulated within the liposome; and wherein the pH sensitive liposome comprises octadecylamine-p (API-L-ASP) 10 (“pH-ADT”). ### Claim 2 (depends on 1) The synthetic nanoparticle of claim 1, wherein apolipoprotein is apolipoprotein A-I (Apo-A1), apolipoprotein A-II, or apolipoprotein E. ### Claim 3 (depends on 1) The synthetic nanoparticle of claim 1, wherein the pH sensitive liposome comprises a pH sensitive phospholipid. ### Claim 4 (depends on 1) The synthetic nanoparticle of claim 1, wherein the pH sensitive liposome further comprises egg-phosphatidylcholine, lipids egg-phosphatidylcholine (EPC), 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy (polyethylene glycol)-2000] (DSPE-PEG2000), DSPE-PEG-Cy 5, and/or a combination thereof. ### Claim 5 (depends on 1) The synthetic nanoparticle of claim 1, wherein the synthetic nanoparticle has a largest cross-sectional dimension of less than or equal to 1000 nanometers (nm). ### Claim 6 (depends on 1) The synthetic nanoparticle of claim 1, wherein the drug is andrographolide and/or derivative thereof. ### Claim 7 (depends on 1) The synthetic nanoparticle of claim 1, wherein the synthetic nanoparticle has a zeta potential between about 0 and about −5, 0 and about −4, or about −1 and about −3 in a solution of about pH 7.4. ### Claim 8 (depends on 1) The synthetic nanoparticle of claim 1, wherein the synthetic nanoparticle binds to scavenger receptor B-1 (SR-B1). ### Claim 9 (depends on 1) The synthetic nanoparticle of claim 1, wherein the synthetic nanoparticle further comprises a nanostructure core on the interior of the pH sensitive liposome. ### Claim 10 (depends on 9) The synthetic nanoparticle of claim 9, wherein the nanostructure core comprises an organic nanostructure core or an inorganic nanostructure core. ### Claim 11 (depends on 1) A method of treating a subject who has cancer, comprising, administering an effective amount of the synthetic nanoparticle of claim 1. ### Claim 12 (depends on 11) The method of claim 11, wherein the cancer is selected from: B-cell lymphoma and T-cell lymphoma. ### Claim 13 (depends on 11) The method of claim 11, wherein the effective amount of the nanoparticle comprises a sub-therapeutic amount of a drug, wherein a sub-therapeutic amount comprises an amount that is less than a minimal amount required for producing a therapeutic result, optionally wherein the effective amount of the nanoparticle comprises a sub-therapeutic amount of a drug in a buffer or alcohol carrier. ### Claim 14 (depends on 1) A method of reducing, in a population of cells, the number of live cancer cells, the method comprising: contacting the cancer cells with a synthetic nanoparticle of claim 1, wherein the synthetic nanoparticle is in an effective amount to induce apoptosis in the cancer cells. ### Claim 15 (depends on 1) A method of treating a subject who has a stroke or has suffered from a stroke, comprising, administering an effective amount of the synthetic nanoparticle of claim 1 to the subject. ### Claim 16 (depends on 1) A method for modulating an immune response in a subject, comprising, administering to the subject an effective amount to modulate an immune response of the synthetic nanoparticle of claim 1. ### Claim 17 (depends on 1) A method of inhibiting viral activity in a subject, comprising, administering to the subject an effective amount to inhibit viral activity of the synthetic nanoparticle of claim 1. ### Claim 18 (depends on 1) A method of increasing macrophage activity in a subject, comprising, administering an effective amount to inhibit viral activity of the synthetic nanoparticle of claim 1.