# US 2020/0399304 A1 · Deoxynucleic Guanidines (DNG)- Modified Oligonucleotides and Methods of Synthesizing Deoxynucleic Guanidine Strands > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2020/0399304 A1 - Document ID: US20200399304A1 - Status: Published application - Kind: A1 - Application number: 16/906,619 - Filed: 2020-06-19 - Published: 2020-12-24 - Earliest claimed: 2019-06-21 - Assignees: Northwestern University - Applicants: Northwestern University - Inventors: Chad A. Mirkin; Kacper Skakuj; Katherine E. Bujold - Web page: https://patentgrep.com/patent/US20200399304A1 ## CPC - C07H 1/00: Processes for the preparation of sugar derivatives - C07H 21/04: with deoxyribosyl as saccharide radical - A61K 9/5115: {Inorganic compounds} - A61K 31/7125: Nucleic acids or oligonucleotides having modified internucleoside linkage, i.e. other than 3'-5' phosphodiesters - A61K 47/02: Inorganic compounds - C12N 15/11: DNA or RNA fragments; Modified forms thereof (DNA or RNA not used in recombinant technology, C07H21/00); {Non-coding nucleic acids having a biological activity} - C12N 15/113: Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; {Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing (when used in plants C12N15/8218)} - C12N 15/85: for animal cells - B82Y 5/00: Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery - C12N 2310/11: Antisense - C12N 2310/14: interfering nucleic acids [NA] - C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13) - 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) - C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00) - B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES ## Abstract Disclosed herein are spherical nucleic acids (SNAs) comprising oligonucleotides comprising one or more modified oligonucleotides, and methods of use thereof. Also disclosed are methods of synthesizing modified oligonucleotides for use in therapeutics, including deoxynucleic guanidine (DNG)-modified oligonucleotides. ## Claims ### Claim 1 A spherical nucleic acid (SNA) comprising a nanoparticle functionalized with an oligonucleotide comprising at least one deoxynucleic guanidine modification (DNG). ### Claim 2 (depends on 1) The SNA of claim 1, wherein the nanoparticle comprises an inorganic material. ### Claim 3 (depends on 1) The SNA of claim 1, wherein the nanoparticle comprises gold, silver, or platinum. ### Claim 4 (depends on 3) The SNA of claim 3, wherein the nanoparticle comprises gold. ### Claim 5 (depends on 1) The SNA of claim 1, wherein the nanoparticle comprises an organic material. ### Claim 6 (depends on 5) The SNA of claim 5, wherein the nanoparticle comprises a liposome. ### Claim 7 (depends on 1) The SNA of claim 1, wherein the oligonucleotide comprises 1 to 20 nucleotides. ### Claim 8 (canceled) ### Claim 9 (depends on 1) The SNA of claim 1, wherein the oligonucleotide comprises 1 to 10 DNGs. ### Claim 10 (canceled) ### Claim 11 (canceled) ### Claim 12 (depends on 1) The SNA of claim 1, wherein at least one DNG comprises thymine. ### Claim 13 (depends on 1) The SNA of claim 1, wherein the oligonucleotide comprises at least one DNG at the 5′ end. ### Claim 14 (depends on 1) The SNA of claim 1, wherein the oligonucleotide comprises at least one DNG at the 3′ end. ### Claim 15 (depends on 1) The SNA of claim 1, wherein the oligonucleotide comprises at least one DNG at the both the 5′ and 3′ ends. ### Claim 16 (depends on 1) A method for transfecting a cell comprising contacting the cell with the SNA of claim 1. ### Claim 17 (canceled) ### Claim 18 (depends on 1) A method for treating a disease or disorder comprising administering a therapeutically effective amount of the SNA of claim 1. ### Claim 19 A method for synthesizing a deoxynucleic guanidine oligonucleotide comprising admixing an aminonucleoside with a thiourea nucleoside in the presence of an electrophilic iodine reagent, a base, and a solvent to form a deoxynucleic guanidine oligonucleotide, wherein the base has a pKa of about 7 to about 11, lacks α-protons, or both. ### Claim 20 (depends on 19) The method of claim 19, wherein the iodine reagent comprises hydroxyl tosyloxy iodobenzene (HTIB), 2-chloro-1-methyl-pyridinium iodide (CMPI), iodine (I2)/triphenylphosphine, 1,3-diiodo-5,5-dimethylhydantoin (DIH), N-iodosuccinimide (NIS), or iodine (I2). ### Claim 21 (canceled) ### Claim 22 (depends on 19) The method of claim 19, wherein the base comprises N-methylimadazole (NMI), N,N-dimethylaminopyridine (DMAP), 2,2,6,6-tetramethylpiperidine (TMP), triethylamine (TEA), 1,2,2,6,6-pentamethylpiperidine (PMP), or 1,4-diazabicyclo[2.2.2]octane (DABCO). ### Claim 23 (canceled) ### Claim 24 (depends on 22) The method of claim 22, wherein the base comprises 2,2,6,6-tetramethylpiperidine (TMP). ### Claim 25 (depends on 19) The method of claim 19, wherein the ratio of base to electrophilic iodine is about 2:1 to about 4:1. ### Claim 26 (canceled) ### Claim 27 (depends on 19) The method of claim 19, wherein the thiourea nucleoside is present in a 1:1 ratio with respect to the electrophilic iodine. ### Claim 28 (canceled) ### Claim 29 (canceled)