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US 12,459,898 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.
Claims32
A composition comprising
- (i) at least one 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 and 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 or CR″;
- R″ is H or C1-C6 alkyl, wherein the alkyl group may be optionally substituted and may combine with any of Ra, Rb, and Rc to form a ring;
- each occurrence of Z is independently a counterion;
- 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 and C10-C13 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, 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 or CR″;
- R″ is H or C1-C6 alkyl, wherein the alkyl group may be optionally substituted and may combine with any of Ra, Rb, and Rc to form a ring;
- each occurrence of Z is independently a counterion;
- 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
- (ii) at least one selected from the group consisting of a pharmaceutically acceptable carrier, base material, antimicrobial agent, a second compound or a moiety, and any combination thereof.
23 more elements
A composition comprising
- (i) at least one 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 and 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, Re, 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 or CR″;
- R″ is H or C1-C6 alkyl, wherein the alkyl group may be optionally substituted and may combine with any of Ra, Rb, and Rc to form a ring;
- each occurrence of Z is independently a counterion;
- 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 and C10-C13 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, 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 or CR″;
- R″ is H or C1-C6 alkyl, wherein the alkyl group may be optionally substituted and may combine with any of Ra, Rb, and Rc to form a ring;
- each occurrence of Z is independently a counterion;
- 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
- (ii) at least one second compound or moiety selected from the group consisting of a QAC, an antimicrobial peptide, a sugar, an iron siderophore, a solid surface, a poly (alkyl ether), and a nucleophilic residue.
23 more elements
Dependencies are inferred from the claim text.