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Covalent conjugates between artemisinin-related endoperoxides and iron-carrying proteins and methods of use

A peroxide, correlation technology, applied in the direction of animal/human protein, transferrin, peptide/protein composition, etc.

Inactive Publication Date: 2005-09-14
UNIV OF WASHINGTON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently, there is no vaccine available for the N. meningitidis type B strain, the most prevalent strain in the Western world

Method used

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  • Covalent conjugates between artemisinin-related endoperoxides and iron-carrying proteins and methods of use
  • Covalent conjugates between artemisinin-related endoperoxides and iron-carrying proteins and methods of use
  • Covalent conjugates between artemisinin-related endoperoxides and iron-carrying proteins and methods of use

Examples

Experimental program
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Embodiment 1

[0088] This example describes the preparation of representative compositions of the invention comprising one or more artemisinin-related endoperoxide molecules covalently linked to a holotransferrin molecule.

[0089] Synthesis of Artelinic acid hydrazide (ART-NH-NH 2 ): Attempts to prepare hydrazide derivatives of artesunate were unsuccessful, resulting in the formation of dihydroartemisinin due to a cyclization reaction. Atriptyline esters were synthesized from dihydroartemisinin as described above (Shrimali et al. (1998) Indian J Chem. 37B: 1161-1163). Artelinic acid (0.1 g, 0.24 mmol) was dissolved in anhydrous acetonitrile (0.48 mL). To this solution was added 1-hydroxybenzotriazole (HOBt) (0.038 g, 0.29 mmol), followed by ethyldimethylethylcarbodiimide (0.055 g, 0.29 mmol). The reaction mixture was stirred at room temperature and monitored by thin layer chromatography (TLC) until all the acid was converted to the HOBt ester.

[0090] A solution of hydrazine (0.46 mL, ...

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Abstract

In one aspect, the invention provides covalent conjugates between artemisinin related endoperoxides and iron-carrying proteins. In some embodiments, the covalent conjugates comprise artelinate and holotransferrin. In another aspect, the invention provides methods for administering the covalent conjugates of the invention to treat cancer and infections by pathogens that bind iron-carrying proteins.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Application No. 60 / 386,928 filed June 6, 2002 under 35 U.S.C. 119. field of invention [0003] The present invention relates to covalent conjugates between artemisinin-associated endoperoxides and iron-carrying proteins and the usefulness of these conjugates in the treatment of cancer and disease caused by pathogens that bind iron-carrying proteins. application in infections. Background of the invention [0004] Artemisinins are sesquiterpene lactones isolated from the plant Artemisia annua L, the extract of which has been used to treat malaria for at least 1600 years. Artemisinin molecules contain endoperoxide bridges, which react with iron atoms to form free radicals. The antimalarial effect of artemisinin is due to its reaction with the heme in the parasite to form free radicals, resulting in cell dea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/14A61K38/16A61K9/20A61K9/48A61K31/00A61K31/295A61K31/335A61K31/357A61K31/366A61K31/555A61K38/00A61P31/00A61P31/04A61P35/00A61P39/06C07D493/18C07K14/79C07K14/795C07K14/805
CPCA61K38/40A61K31/00A61K31/555A61K31/357A61K31/335A61K31/295A61P31/00A61P31/04A61P33/00A61P35/00A61P39/06A61K2300/00
Inventor H·C·莱T·佐佐木N·P·辛格
Owner UNIV OF WASHINGTON
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