Curcumin conjugates and methods of use thereof
AssigneeAugusta University Research Institute, Inc.
InventorSiva Panda
Life of this patent
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Abstract
Curcumin-based conjugates and methods of use thereof are provided. Pharmaceutical compositions including an effective amount of one or more curcumin conjugates are also provided. In particular embodiments, the compositions are formulated for oral delivery. The conjugates and pharmaceutical compositions thereof can be administered to a subject in need thereof to treat a host of diseases and disorders including but not limited to, cancer, inflammation, and microbial growth.
Claims12
A curcumin conjugate of the general formula
- wherein the dotted lines between A and C1, C1 and C2, C2 and C3 and C3 and D indicate that a single or double bond may be present, as valence permits,
- wherein the dotted lines between A and M, and D and Q indicate that a single bond or no bond may be present, as valence permit,
- wherein C1, C2, and C3 are carbon atoms,
- wherein A and D are oxygen atoms,
- wherein M and Q are independently absent, or hydrogen, as valence permits,
- wherein R2 and R3 can be one or more amino acids or salts thereof, nucleic acids, lipids, polysaccharides, polymers, substituted or unsubstituted alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, or other organic groups containing between C1 and C10 carbon atoms, inclusive,
- wherein R1 and R4 can be carboxybenzyl (Cbz), or fluorenylmethyloxycarbonyl (FMOC), and
- wherein L1 and L2 can be independently absent, substituted or unsubstituted alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, or other organic groups containing between C1 and C10 carbon atoms, inclusive or a combination thereof or pharmaceutically acceptable salt(s), polymorph(s), solvent(s), hydrate(s), crystal forms, and/or enantiomer(s) thereof.
A pharmaceutical composition comprising a curcumin conjugate selected from the group consisting of ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) bis(2-(((benzyloxy)carbonyl)amino)propanoate), ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2′S)-bis(2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanoate), ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) bis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)acetate), ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2'S)-bis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(methylthio)butanoate), ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2R,2′R)-bis(2-(((benzyloxy)carbonyl)amino)propanoate), and ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2R,2′R)-bis(2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanoate), or a combination thereof or pharmaceutically acceptable salt(s), polymorph(s), solvent(s), hydrate(s), crystal forms, and/or enantiomer(s) thereof.
Dependencies are inferred from the claim text.