Antihelminthic anthraquinones and method of use thereof
AssigneesBoard of Trustees of Michigan State University, The Regents of the University of California
InventorsRobert H. Cichewicz, Muraleedharan G. Nair, James H. McKerrow
Life of this patent
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Abstract
Anthraquinones are described which are antihelminthic and in particular, are useful in compositions for inhibiting Schistosoma sp. in vitro or in vivo. The preferred anthraquinones have the formula: 1 wherein R1, R2, R3, and R4 are each hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, or combination thereof, R is a group containing 1 to 12 carbons such as methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, or combination thereof, and the halogen is I, F, Br, or Cl.
Claims33
A method for inhibiting a parasitic helminth which comprises:
- exposing the helminth to an inhibitory amount of an anthraquinone.
A method of inhibiting a parasitic helminth, which comprises:
- exposing the helminth to an antihelminthic amount of at least one anthraquinone of the formula:
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- wherein R1, R2, R3, and R4 are each selected from the group consisting of hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, and combinations thereof, R is a group containing 1 to 12 carbons selected from the group consisting of methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, and combinations thereof, and the halogen is selected from the group consisting of I, F, Br, and Cl.
A method of inhibiting a Schistosoma sp. which comprises:
- exposing the Schistosoma sp. to an inhibitory amount of at least one anthraquinone of the formula:
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- wherein R1, R2, R3, and R4 are each selected from the group consisting of hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, and combinations thereof, R is a group containing 1 to 12 carbons selected from the group consisting of methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, and combinations thereof, and the halogen is selected from the group consisting of I, F, Br, and Cl.
A method for inhibiting a pathogenic trematode in a warm-blooded animal or human infected with the pathogenic trematode comprising:
- (a) providing a composition containing an inhibitory amount of at least one anthraquinone selected from the group consisting of 1,2,8-trihydroxy-3-methyl anthraquinone (compound 3) and 1,2,8-trihydroxy-3-hydroxymethyl anthraquinone (compound 6) in a pharmaceutically acceptable carrier;
- and
- (b) and administering the composition to the warm-blooded animal or human to inhibit the pathogenic trematode.
A method for inhibiting a pathogenic trematode in a warm-blooded animal or human infected with the pathogenic trematode comprising:
- (a) providing a composition containing an inhibitory amount of 1,2,8-trihydroxy-3-methyl-O-β-D-glucopyranoside anthraquinone (compound 7) and at least one anthraquinone selected from the group consisting of 1,8-dihydroxy-2-O-β-D-glucopyranoside anthraquinone (compound 4) and 1,8-dihydroxy-2-O-malonyl-(1-6)-β-D-glucopyranoside anthraquinone (compound 5) in a pharmaceutically acceptable carrier;
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- (b) and administering the composition to the warm-blooded animal or human to inhibit the pathogenic trematode.
An antihelminthic composition which comprises:
- (a) at least one anthraquinone of the formula:
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- wherein R1, R2, R3, and R4 are each selected from the group consisting of hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, and combinations thereof, R is a group containing 1 to 12 carbons selected from the group consisting of methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, and combinations thereof, and the halogen is selected from the group consisting of I, F, Br, and Cl;
- and
- (b) a pharmaceutically acceptable carrier, wherein the composition contains between about 1 and 1,000 micrograms of the anthraquinone per milliliter or gram of the carrier.
An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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An isolated and purified anthraquinone which has the formula:
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Dependencies are inferred from the claim text.