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US 11,111,216 B2Granted
Polycationic amphiphiles as antimicrobial agents and methods using same
AssigneesTemple University of the Commonwealth System of Higher Education, Villanova University
InventorsWilliam M. Wuest, Kevin P. C. Minbiole
Life of this patent
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Abstract
The present invention includes novel polycationic amphiphilic compounds useful as antimicrobial agents. The present invention further includes methods useful for removing microorganisms and/or biofilm-embedded microorganisms from a surface. The present invention further includes compositions and methods useful for preventing or reducing the growth or proliferation of microorganisms and/or biofilm-embedded microorganisms on a surface.
Claims8
A compound selected from the group consisting of formula I-IV:
- wherein in formula I-III:
- R1, R2, and R3 are each independently selected from the group consisting of H or C1-C25 alkyl, wherein the alkyl group may be optionally substituted with —OR′, —NR′2, —NR′—C(O)R′, —C(O)NR′2, —NR′—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, halogen, benzyl, o-vinylbenzyl, m-vinylbenzyl, p-vinylbenzyl, phenyl, allyl, and substituted allyl, further wherein the alkyl group may optionally be interrupted with a —O—C(O)— group or a —C(O)O— group;
- each occurrence of Ra, Rb, Rc, Rd, and Re is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- each occurrence of R′ is independently selected from the group consisting of H and C1-4 alkyl;
- Y is N;
- each occurrence of Z− is independently selected from the group consisting of Br− and I−;
- m is an integer from 0 to 4;
- n is an integer from 0 to 4;
- and
- p is an integer from 0 to 4;
- and
- wherein in formula IV:
- R1 and R2 are each independently selected from the group consisting of H or C1-C25 alkyl, wherein the alkyl group may be optionally substituted with —OR′, —NR′2, —NR′—C(O)R′, —C(O)NR′2, —NR′—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, halogen, benzyl, o-vinylbenzyl, m-vinylbenzyl, p-vinylbenzyl, phenyl, allyl, and substituted allyl, further wherein the alkyl group may optionally be interrupted with a —O—C(O)— group or a —C(O)O— group, and each occurrence of Z− is I− when R1 and R2 are C12 alkyl;
- each occurrence of Ra and Rb is independently selected from the group consisting of C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- when each occurrence of Rc, Rd, and Re is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- or
- each occurrence of Ra and Rb is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- when each occurrence of Rc, Rd, and Re is independently selected from the group consisting of C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- each occurrence of R′ is independently selected from the group consisting of H and C1-4 alkyl;
- each occurrence of Z− is independently selected from the group consisting of Br− and I−;
- m is an integer from 0 to 4;
- and
- n is an integer from 0 to 4.
20 more elements
A compound selected from the group consisting of formula I-IV:
- wherein in formula I-III:
- R1, R2, and R3 are each independently selected from the group consisting of H or C1-C25 alkyl, wherein the alkyl group may be optionally substituted with —OR′, —NR′2, —NR′—C(O)R′, —C(O)NR′2, —NR′—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, halogen, benzyl, o-vinylbenzyl, m-vinylbenzyl, p-vinylbenzyl, phenyl, allyl, and substituted allyl, further wherein the alkyl group may optionally be interrupted with a —O—C(O)— group or a —C(O)O— group;
- each occurrence of Ra, Rb, Rc, Rd, and Re is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- each occurrence of R′ is independently selected from the group consisting of H and C1-4 alkyl;
- Y is N;
- each occurrence of Z− is independently selected from the group consisting of Br− and I−;
- m is an integer from 0 to 4;
- n is an integer from 0 to 4;
- and
- p is an integer from 0 to 4;
- and
- wherein in formula IV:
- R1 and R2 are each independently selected from the group consisting of —R4—O—C(O)—R5 and —R4—(O)C—O—R5, wherein R4 and R5 are each independently an optionally substituted alkyl chain, provided that the total number of carbon atoms in the alkyl chains of R4 and R5 is 4 to 25 carbon atoms;
- each occurrence of Ra and Rb is independently selected from the group consisting of C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- when each occurrence of Rc, Rd, and Re is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- or
- each occurrence of Ra and Rb is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- when each occurrence of Rc, Rd, and Re is independently selected from the group consisting of C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
- and
- each occurrence of R′ is independently selected from the group consisting of H and C1-4 alkyl;
- each occurrence of Z− is independently selected from the group consisting of Br− and I−;
- m is an integer from 0 to 4;
- and
- n is an integer from 0 to 4.
21 more elements
Dependencies are inferred from the claim text.