# US 10,765,757 B2 · Mucosal delivery of therapeutic molecules, proteins, or particles coupled to ceramide lipids > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,765,757 B2 - Document ID: US10765757B2 - Status: Granted - Kind: B2 - Application number: 15/255,595 - Filed: 2016-09-02 - Published: 2017-04-06 - Granted: 2020-09-08 - Earliest claimed: 2008-09-08 - Assignees: Children's Medical Center Corporation - Applicants: Children's Medical Center Corporation - Inventors: Wayne I. Lencer; Daniel J F Chinnapen; Randy Mrsny - Web page: https://patentgrep.com/patent/US10765757B2 ## CPC - A61K 47/549: {Sugars, nucleosides, nucleotides or nucleic acids} - A61K 31/4164: 1,3-Diazoles - A61K 38/26: Glucagons - A61K 39/15: Reoviridae, e.g. calf diarrhea virus - A61K 47/543: {Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine} - A61K 47/544: {Phospholipids} - A61K 47/61: the organic macromolecular compound being a polysaccharide or a derivative thereof - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C12N 7/00: Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof (preparing medicinal viral antigen or antibody compositions, e.g. virus vaccines, A61K39/00) - C12N 2720/12322: New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes - C12N 2720/12334: Use of virus or viral component as vaccine, e.g. live-attenuated or inactivated virus, VLP, viral protein - 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 - C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00) ## Abstract Described herein are compositions and methods useful for allowing for the absorption (passage) of agents of interest, such as therapeutic agents, across epithelial and mucosal barriers and/or into certain subcellular compartments of the cell, such as the recycling endosome (RE), Golgi, and the endoplasmic reticulum (ER). ## Claims ### Claim 1 A method of delivering an agent into cells or across a mucosal surface, comprising contacting a complex of a delivery vehicle and the agent with the cells or the mucosal surface, under conditions appropriate for uptake of the delivery vehicle or the agent of interest into the cell or absorption of the delivery vehicle or the agent of interest across the mucosal surface, wherein the delivery vehicle comprises a glycosphingolipid that forms a complex with the agent to be delivered, wherein the glycosphingolipid comprises a ceramide consisting of a sphingosine coupled with (a) a short chain fatty acid (C4-C12) or (b) a long chain fatty acid (C14-C28) comprising at least one cis double bond between two carbon atoms and wherein the agent to be delivered is covalently attached to the oligosaccharide of the glycosphingolipid. ### Claim 2 (depends on 1) The method of claim 1, wherein the glycosphingolipid comprises a ganglioside. ### Claim 3 (depends on 2) The method of claim 2, wherein the ganglioside comprises a sialic acid. ### Claim 4 (depends on 3) The method of claim 3, wherein the ganglioside is monosialotetrahexosylganglioside (GM1). ### Claim 5 (depends on 1) The method of claim 1, wherein the glycosphingolipid comprises a globoside. ### Claim 6 (depends on 5) The method of claim 5, wherein the globoside is globotriaosyl ceramide (Gb3). ### Claim 7 (depends on 1) The method of claim 1, wherein the fatty acid is a C4-C12 fatty acid with no double bonds between carbon atoms. ### Claim 8 (depends on 1) The method of claim 1, wherein the fatty acid is a C12 fatty acid with no double bonds between carbon atoms or a C16 fatty acid comprising a cis double bond. ### Claim 9 (depends on 8) The method of claim 8, wherein the fatty acid is C16:1. ### Claim 10 (depends on 1) The method of claim 1, wherein the agent to be delivered is selected from the group consisting of proteins, peptides, nucleic acids, polysaccharides carbohydrates, lipids, glycoproteins, synthetic organic drugs, and inorganic drugs, which exerts a biological effect when administered to a subject. ### Claim 11 (depends on 1) The method of claim 1, wherein the agent to be delivered is a vaccine antigen. ### Claim 12 (depends on 11) The method of claim 11, wherein the vaccine antigen comprises rotavirus VP6 capsid protein. ### Claim 13 (depends on 1) The method of claim 1, wherein the agent to be delivered is a therapeutic agent. ### Claim 14 (depends on 13) The method of claim 13, wherein the therapeutic agent comprises active glucagon-like peptide 1(GLP1) peptide hormone. ### Claim 15 (depends on 13) The method of claim 13, wherein the therapeutic agent is an anti-inflammatory agent, a vaccine antigen, an anti-cancer drug or chemotherapeutic drug, a clotting factor, a hormone, a steroid, a cytokine, an antibiotic, or a drug for the treatment of cardiovascular disease, an infectious disease, an autoimmune disease, allergy, a blood disorder, a metabolic disorder or a skin disease. ### Claim 16 (depends on 15) The method of claim 15, wherein the anti-inflammatory agent comprises clotrimazole. ### Claim 17 A method of delivering an agent into cells or across a mucosal surface, comprising contacting a ganglioside-therapeutic agent complex with the cells or the mucosal surface, under conditions appropriate for uptake of the ganglioside-therapeutic agent complex into the cell or absorption of the ganglioside-therapeutic agent complex across the mucosal surface, wherein the ganglioside-therapeutic agent complex comprises monosialotetrahexosylganglioside (GM1) attached to a therapeutic agent, wherein the GM1 comprises a ceramide consisting of a sphingosine coupled with a fatty acid of: (a) 4-12 carbon atoms with no double bonds between carbon atoms or (b) 14-28 carbon atoms comprising at least one cis double bond between two carbon atoms, and wherein the therapeutic agent is covalently attached to the oligosaccharide of monosialotetrahexosylganglioside (GM1). ### Claim 18 A method of treating a disease or condition in an individual in need thereof, comprising administering an effective amount of a ganglioside-therapeutic agent complex to the individual, wherein the ganglioside-therapeutic agent complex comprises a glycosphingolipid and a therapeutic agent to be administered, wherein the glycosphingolipid comprises a ceramide that consists of a sphingosine coupled with: (a) a short chain fatty acid (C4-C12) or (b) a long chain fatty acid (C14-C28) comprising at least one cis double bond between two carbon atoms, and wherein the therapeutic agent to be administered is covalently attached to the oligosaccharide of the glycosphingolipid, and wherein the effective amount is an amount sufficient to ameliorate/reduce the extent to which the disease or condition occurs in the individual. ### Claim 19 (depends on 1) The method of claim 1, wherein the complex is targeted to recycling endosomes or trans Golgi-network. ### Claim 20 (depends on 17) The method of claim 17, wherein the complex is targeted to recycling endosomes or trans Golgi-network. ### Claim 21 (depends on 18) The method of claim 18, wherein the complex is targeted to recycling endosomes or trans Golgi-network of a cell in the individual.