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US 9,682,100 B2Granted
Cationic polyamines for treatment of viruses
AssigneesInternational Business Machines Corporation, Agency for Science, Technology and Research, National University of Singapore
InventorsJames L. Hedrick, Ichiyama Koji, Naoki Yamamoto, Chuan Yang, Yi Yan Yang
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Abstract
Antiviral cationic polyamines were prepared by modifying polyethylenimines with N-acylating agents that introduce a side chain comprising one or more carbons and at least one alcohol hydroxy group. The cationic polyamines can have a linear or branched polyethylenimine backbone structure. Preferably, the cationic polyamines comprise pendant monosaccharide groups, which can be introduced via a cyclic carbonate comprising a pendant protected monosaccharide (e.g., mannose) group. The cationic polyamines can be active and selective against a broad spectrum of viruses at low concentrations, and are generally non-toxic.
Claims22
A method, comprising:
- treating a virus with a cationic polyamine, the virus comprising DNA and/or RNA, the virus capable of causing a viral disease in mammals, thereby forming a treated virus comprising the cationic polyamine bound by non-covalent interactions to the virus;
- wherein:
- i) the treated virus is less capable of entering a living mammalian cell and/or undergoing replication within a living mammalian cell compared to the virus before said treating,
- ii) the cationic polyamine comprises:
- a plurality of non-charged N-acylated ethylenimine units of formula (1):
- wherein each K′ comprises at least one carbon and at least one alcohol hydroxyl group, and a plurality of positive-charged secondary ethylenimine units of formula (3a):
- wherein the starred bond of the nitrogen is linked to a carbon and X⊖ is a negative-charged counterion bound by non-covalent association with the positive charged nitrogen, and
- iii) the cationic polyamine comprises the N-acylated ethylenimine units and the secondary ethylenimine units arranged in a random distribution and linked covalently head-to-tail, wherein nitrogen 1 of a given ethylenimine unit is linked to carbon 3 of a different ethylenimine unit,
- wherein the virus is selected from the group consisting of dengue fever viruses, SARS corona viruses, Chikungunya viruses, enteroviruses, influenza viruses, herpes simplex viruses, and combinations thereof.
6 more elements
A method, comprising:
- treating a living mammalian cell with a cationic polyamine, the cell comprising a cell membrane, thereby forming a treated cell comprising the cationic polyamine bound by non-covalent interactions to the cell membrane;
- wherein:
- i) the treated cell has more resistance to a virus entering the treated cell and/or replicating within the treated cell compared to the untreated cell before said treating, the virus comprising DNA and/or RNA, the virus capable of causing a viral disease in mammals,
- ii) the cationic polyamine comprises:
- a plurality of non-charged N-acylated ethylenimine units of formula (1):
- wherein each K′ comprises at least one carbon and at least one alcohol hydroxyl group, and a plurality of positive-charged secondary ethylenimine units of formula (3a):
- wherein the starred bond of the nitrogen is linked to a carbon, and X⊖ is a negative-charged counterion bound by non-covalent association with the positive charged nitrogen, and
- iii) the cationic polyamine comprises the N-acylated ethylenimine units and the secondary ethylenimine units arranged in a random distribution and linked covalently head-to-tail, wherein nitrogen 1 of a given ethylenimine unit is linked to carbon 3 of a different ethylenimine unit,
- wherein the virus is selected from the group consisting of dengue fever viruses, SARS corona viruses, Chikungunya viruses, enteroviruses, influenza viruses, herpes simplex viruses, and combinations thereof.
6 more elements
A method, comprising:
- administering to a patient infected with a virus a therapeutically effective amount of a cationic polyamine, thereby inhibiting replication of the virus, the virus comprising DNA and/or RNA, the virus capable of causing a viral disease in mammals, the cationic polyamine bound by non-covalent interactions to the virus;
- wherein:
- i) the cationic polyamine comprises:
- a plurality of non-charged N-acylated ethylenimine units of formula (1):
- wherein each K′ comprises at least one carbon and at least one alcohol hydroxyl group, and a plurality of positive-charged secondary ethylenimine units of formula (3a):
- wherein the starred bond of the nitrogen is linked to a carbon, and X⊖ is a negative-charged counterion bound by non-covalent association with the positive charged nitrogen, and
- ii) the cationic polyamine comprises the N-acylated ethylenimine units and the secondary ethylenimine units arranged in a random distribution and linked covalently head-to-tail, wherein nitrogen 1 of a given ethylenimine unit is linked to carbon 3 of a different ethylenimine unit,
- wherein the virus is selected from the group consisting of dengue fever viruses, SARS corona viruses, Chikungunya viruses, enteroviruses, influenza viruses, herpes simplex viruses, and combinations thereof.
5 more elements
Dependencies are inferred from the claim text.