IP Library › Granted Patent US 12,552,933
Granted Patent B2
US 12,552,933 · App. 18/333,173 · Granted Feb 17, 2026

Polylysine polymers with antimicrobial and/or anticancer activity

Inventors: Nathaniel H. Park (San Jose, CA); James L. Hedrick (Pleasanton, CA); Victoria A. Piunova (Los Gatos, CA); Gavin Jones (San Jose, CA); Yi Yan Yang (Singapore, SG); Pang Kern Jeremy Tan (Singapore, SG); Chuan Yang (Hillington Green, SG); Cherylette Anne Alexander (Singapore, SG)
Assignees: INTERNATIONAL BUSINESS MACHINES CORPORATION; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH
C08L79/02A61K45/06
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Quick Facts
Patent No.
US 12,552,933
App. No.
18/333,173
Granted
Feb 17, 2026
Kind
B2
Abstract

Techniques regarding guanidinium functionalized polylysine polymers that can have antimicrobial and/or anticancer activity are provided. For example, one or more embodiments described herein can comprise a chemical composition, which can comprise a polymer comprising a molecular backbone covalently bonded to a pendent guanidinium functional group, wherein the molecular backbone can comprise a polylysine structure.

Claims (28)

1 . A method, comprising:

inhibiting a pathogen by contacting a cell of the pathogen with an antimicrobial polymer, wherein the antimicrobial polymer comprises a polylysine structure and comprises 50% or greater functionalization with a pendent guanidium functional group.

2 . The method of claim 1 , wherein the inhibiting is facilitated by the antimicrobial polymer via a translocation mechanism that comprises translocating the antimicrobial polymer through a membrane of the cell and precipitating a biomacromolecule within a cytosol of the cell.

3 . The method of claim 1 , wherein the antimicrobial polymer is comprised within a coacervate complex that further comprises an anionic polymer.

4 . The method of claim 3 , wherein the anionic polymer comprises another polylysine structure functionalized with a pendent anionic functional group.

5 . The method of claim 4 , wherein the pendent anionic functional group is selected from a group consisting of: a sulfonate group, a carboxylate group, a boronate group, and a phosphate group.

6 . The method of claim 1 , wherein the antimicrobial polymer is comprised within a combination therapy with an antimicrobial agent, wherein the antimicrobial polymer enhances an antimicrobial activity of the antimicrobial agent.

7 . The method of claim 1 , wherein the pathogen comprises a Gram-negative bacterium.

8 . The method of claim 1 , wherein the pathogen comprises a Gram-positive bacterium.

9 . The method of claim 1 , wherein the pathogen comprises a fungus.

10 . The method of claim 1 , wherein the pathogen comprises a yeast.

11 . The method of claim 1 , wherein the antimicrobial polymer is characterized by a chemical formula:

wherein “m” is a first number greater than or equal to 5 and less than or equal to 30; and

wherein “n” is a second number greater than or equal to 0 and less than or equal to 25.

12 . The method of claim 1 , wherein the polymer comprises 70% or greater functionalization with the pendent guanidium functional group.

13 . A method, comprising:

administering an antimicrobial polymer to a patient afflicted by a pathogen, wherein the antimicrobial polymer comprises a polylysine structure and comprises 50% or greater functionalization with a pendent guanidium functional group; and

inhibiting the pathogen as a result of the administering.

14 . The method of claim 13 , wherein the pathogen is selected from a group consisting of: a Gram-negative bacterium, a Gram-positive bacterium, a fungus, and yeast.

15 . The method of claim 13 , wherein the antimicrobial polymer is comprised within a coacervate complex that further comprises an anionic polymer.

16 . The method of claim 13 , wherein the antimicrobial polymer is characterized by a chemical formula:

wherein “m” is a first number greater than or equal to 5 and less than or equal to 30; and

wherein “n” is a second number greater than or equal to 0 and less than or equal to 25.

17 . A method, comprising:

inhibiting a pathogen by contacting a cell of the pathogen with an antimicrobial polymer, wherein the antimicrobial polymer comprises a polylysine structure functionalized with a pendent guanidinium functional group, and wherein the antimicrobial polymer is comprised within a coacervate complex that further comprises an anionic polymer.

18 . The method of claim 17 , wherein the anionic polymer comprises another polylysine structure functionalized with a pendent anionic functional group.

19 . The method of claim 18 , wherein the pendent anionic functional group is selected from a group consisting of: a sulfonate group, a carboxylate group, a boronate group, and a phosphate group.

20 . The method of claim 17 , wherein the pathogen comprises a yeast or a fungus.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2023
From: PARK, NATHANIEL H.; HEDRICK, JAMES L.; PIUNOVA, VICTORIA A.; JONES, GAVIN
To: INTERNATIONAL BUSINESS MACHINES CORPORATION
Reel/Frame 064478/0595 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2023
From: YANG, YI YAN; TAN, PANG KERN JEREMY; YANG, CHUAN; ALEXANDER, CHERYLETTE ANNE
To: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH
Reel/Frame 064478/0675 →
Continuity (3)
Division 17241768 · Apr 27, 2021
Division 16531432 · Aug 5, 2019
Related Publication 20230331988A1 · Oct 19, 2023
References Cited (90)
US 6190650B1 · Matthews et al. · 2001 [cited by applicant]
US 7655400B2 · Maruyama · 2010 [cited by applicant]
US 9854806B2 · Chin et al. · 2018 [cited by applicant]
US 9976074B2 · Stanciu et al. · 2018 [cited by applicant]
US 10155009B2 · Nagasaki et al. · 2018 [cited by applicant]
US 11007216B2 · Hedrick et al. · 2021 [cited by applicant]
US 11028264B2 · Park et al. · 2021 [cited by applicant]
US 11725107B2 · Park et al. · 2023 [cited by applicant]
US 20020009491A1 · Rothbard et al. · 2002 [cited by applicant]
US 20080312172A1 · Giles-Komar et al. · 2008 [cited by applicant]
US 20100134904A1 · Tsai · 2010 [cited by applicant]
US 20110109151A1 · Seidinger · 2011 [cited by applicant]
US 20110311463A1 · Diamond et al. · 2011 [cited by applicant]
US 20120045400A1 · Nowak · 2012 [cited by examiner]
US 20140193517A1 · Agarwal et al. · 2014 [cited by applicant]
US 20150038671A1 · Parang et al. · 2015 [cited by applicant]
US 20160338356A1 · Chen et al. · 2016 [cited by applicant]
US 20180020669A1 · Charles et al. · 2018 [cited by applicant]
US 20180157786A1 · Dakshanamurthy et al. · 2018 [cited by applicant]
US 20190388460A1 · Hedrick et al. · 2019 [cited by applicant]
CN 1694894A · 2005 [cited by applicant]
CN 103998035A · 2014 [cited by applicant]
CN 108184852A · 2018 [cited by applicant]
CN 108430482A · 2018 [cited by applicant]
CN 108694991A · 2018 [cited by applicant]
CN 114174276A · 2022 [cited by applicant]
CN 114245740A · 2022 [cited by applicant]
DE 112020002988T5 · 2022 [cited by applicant]
DE 112020002996T5 · 2022 [cited by applicant]
EP 1466583B1 · 2008 [cited by applicant]
EP 3747932A · 2020 [cited by applicant]
FR 2851465A1 · 2004 [cited by examiner]
GB 2601667A · 2022 [cited by applicant]
GB 2601680A · 2022 [cited by applicant]
JP 2004315820A · 2004 [cited by applicant]
JP 2006070036A · 2006 [cited by applicant]
JP 2022543408A · 2022 [cited by applicant]
JP 2022543409A · 2022 [cited by applicant]
WO 2005007098A2 · 2005 [cited by applicant]
WO 2005085432A1 · 2005 [cited by applicant]
WO 2010134904A1 · 2010 [cited by applicant]
WO 2011109151A1 · 2011 [cited by applicant]
WO 2016024999A1 · 2016 [cited by applicant]
WO 2016123368A1 · 2016 [cited by applicant]
WO 2016167333A1 · 2016 [cited by applicant]
WO 20160186581A1 · 2016 [cited by applicant]
WO 2017053778A1 · 2017 [cited by applicant]
WO 2017066242A1 · 2017 [cited by applicant]
WO 2018015665A1 · 2018 [cited by applicant]
WO 2021024054A1 · 2021 [cited by applicant]
WO 2021024057A1 · 2021 [cited by applicant]
Kolpin et al., “Pharmaceuticals, Hormones and Other Organic Wastewater Contaminants in U.S. Streams, 1999-2000: A National Reconnaissance”, Environmental Science & Technology, 2002, vol. 36, No. 6, 1202-1211, 12 pages. [cited by applicant]
Hoque et al., “Broad Spectrum Antibacterial and Antifungal Polymeric Paint Materials: Synthesis, Structure-Activity Relationship, and Membrane-Active Mode of Action”, ACS Applied Materials & Interfaces, Dec. 26, 2014, v… [cited by applicant]
Harbut et al., “Auranofin Exerts Broad-spectrum Bactericidal Activities by Targeting Thiol-redox Homeostasis”, Proceedings of the National Academy of Sciences, vol. 112, No. 14, Apr. 7, 2015, 6 pages. [cited by applicant]
Padhy et al. “Drug Repositioning: Re-investigating Existing Drugs for New Therapeutic Indications”, Journal Postgraduate Medicine, vol. 57, No. 2, 2011, 7 pages. [cited by applicant]
Younis et al., “Repurposing Nonantimicrobial Drugs And Clinical Molecules to Treat Bacterial Infections”, Current Pharmaceutical Design, vol. 21, No. 28, 2015, 11 pages. [cited by applicant]
Brochado et al., “Species-specific Activity Of Antibacterial Drug Combinations”, Nature, vol. 559, No. 7713, Jul. 2018, 42 pages. [cited by applicant]
Chin et al., “A Macromolecular Approach to Eradicate Multidrug Resistant Bacterial Infections While Mitigating Drug Resistance Onset”, Nature Communications, vol. 6, No. 917, 2018, 14 pages. [cited by applicant]
Piccaro et al., “ Rifampin Induces Hydroxyl Radical Formation in Mycobacterium Tuberculosis”, Antimicrobial Agents and Chemotherapy, vol. 58, No. 12, Dec. 2014, 7527-7533, 7 pages. [cited by applicant]
Hedrick et al., “Utilizing Polymers and Antibiotics to Enhance Antimicrobial Activity and Inhibit Antibiotic Resistance”, U.S. Appl. No. 16/144,040, filed Sep. 27, 2018. 56 pages. [cited by applicant]
List of IBM Patents or Applications Treated as Related (Appendix P), 2 pages. [cited by applicant]
Non-Final Office Action received for U.S. Appl. No. 16/531,432 dated Aug. 24, 2020, 54 pages. [cited by applicant]
Non-Final Office Action received for U.S. Appl. No. 16/531,493 dated Jul. 23, 2020, 32 pages. [cited by applicant]
Cho et al., “Molecular Weight and Charge Density Effects of Guanidinylated Biodegradable Polycarbonates on Antimicrobial Activity and Selectivity”, Biomacromolecules, vol. 19, 2017, 1389-1401, 13 pages. [cited by applicant]
Ogrendik et al., “Antibiotics for the Treatment of Rheumatoid Arthritis”, International Journal of General Medicine, vol. 7, 2014, 43-47, 5 pages. [cited by applicant]
Dall et al., “Synthetic Polymers Show Promise Against Multidrugresistant Microbes”, Center for Infectious Disease Research and Policy, April, 9, 2018, 3 pages. [cited by applicant]
Thangamani et al., “Antibacterial Activity and Mechanism of Action of Auranofin Against Multi-drug Resistant Bacterial Pathogens”, Scientific Reports, 2016, vol. 6, No. 22571, 1-13, 13 pages. [cited by applicant]
International Search Report and Written Opinion received for PCT Application Serial No. PCT/IB2020/056650 dated Nov. 3, 2020, 11 pages. [cited by applicant]
Ei-Sersy et al., “Antibacterial and Anticancer Activity of E-poly-l-lysine (ϵ-pl) Produced by a Marine [cited by applicant]
Santos et al., “Recent Developments in Antimicrobial Polymers: A Review”, Materials, vol. 9, Jul. 20, 2016, 33 pages. [cited by applicant]
Pantos et al., “Guanidinium Group: A Versatile Moiety Inducing Transport and Multicompartmentalization in Complementary Membranes”, Biochimica et Biophysica Acta, vol. 1778, 2008, pp. 811-823, 13 pages. [cited by applicant]
Exley et al., “Antimicrobial Peptide Mimicking Primary Amine and Guanidine Containing Methacrylamide Copolymers Prepared by Raft Polymerization”, Biomacromolecules, vol. 16, Nov. 11, 2015, pp. 3845-3852, 8 pages. [cited by applicant]
International Search Report and Written Opinion received for PCT Application Serial No. PCT/IB2020/056644 dated Nov. 3, 2020, 11 pages. [cited by applicant]
Song et al., “β-methasone-containing Biodegradable Poly(Lactide-coglycolide) Acid Microspheres for Intraarticular Injection: Effect of Formulation Parameters on Characteristics and in Vitro Release”, Pharmaceutical Deve… [cited by applicant]
Pearson et al., “Glycopolymer Self-Assemblies with Gold(I)Complexed to the Core as a Delivery System for Auranofin”, Macromolecules, 2015, 12 pages. [cited by applicant]
Dangol et al., “Innovative Polymeric System (Ips) for Solvent-free Lipophilic Drug Transdermal Delivery Via Dissolving Microneedle”, Journal of Controlled Release, vol. 223, 2015, 26 pages. [cited by applicant]
Examination Report Under Section 18(3) received for GB patent Application Serial No. GB2202615.7 dated Sep. 12, 2022, 4 pages. [cited by applicant]
Reply to Examination Report under Section 18(3) for GB Application No. GB2202615.7 dated Oct. 5, 2022, 2 pages. [cited by applicant]
Office Action received for German Patent Application Serial No. DE112020002996.4 dated Jan. 26, 2023, 7 pages. [cited by applicant]
Wagner et al., “Properties of Basic Amino-Acid Residues”, European Journal of Biochemistry, vol. 46, 1974, pp. 27-34. [cited by applicant]
Notice of Allowance received for U.S. Appl. No. 17/241,768 dated Mar. 22, 2023, 38 pages. [cited by applicant]
Notice of Allowance received for U.S. Appl. No. 16/531,493 dated Apr. 23, 2023, 13 pages. [cited by applicant]
Office Action received for Chinese Patent Application Serial No. 202080052897.6 dated Jul. 22, 2023, 9 pages. [cited by applicant]
Notice of Reasons for Refusal for Japanese Patent Application No. 2022-506794 dated Nov. 14, 2023, 14 pages. [cited by applicant]
First Office Action received for Chinese Patent Application Serial No. 202080053659.7 dated Dec. 29, 2023, 13 pages(Including English Translation). [cited by applicant]
Second Office Action received for Chinese Patent Application Serial No. 202080052897.6 dated Jun. 1, 2024, 11 pages(Including English Translation). [cited by applicant]
Notice of Reasons for Refusal for Japanese Patent Application No. 2022-506793 dated Nov. 8, 2023. [cited by applicant]
Yanagawa, et al., “Anti-bacterial and anti-fungal effect of several anti-rheumatic drugs,” Journal of Inflammation, 1995, vol. 15, No. 3, pp. 261-264. [cited by applicant]
Chin, et al., “A macromolecular approach to eradicate multidrug resistant bacterial infections while mitigating drug resistance onset,” Nature Communications, 2018, vol. 9, pp. 1-14. [cited by applicant]
German Patent and Trademark Office, “Office Action,” Jan. 30, 2025, 10 Pages, DE Application No. 112020002996.4. [cited by applicant]