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Method of preparing and use of prodrugs of betulinic acid derivatives

a technology of betulinic acid and derivatives, which is applied in the field of compositions and methods of inhibiting tumors, can solve the problems of difficult production of betulinic acid-containing pharmacological formulations, and achieve the effects of preventing or inhibiting tumor growth, preventing or inhibiting the growth of malignant tumors, and improving the bioavailability of betulinic acid

Inactive Publication Date: 2007-03-29
THE BOARD OF TRUSTEES OF THE UNIV OF ILLINOIS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013] Therefore, an important aspect of the present invention is to provide a method and composition for preventing or inhibiting tumor growth and, particularly, for preventing or inhibiting the growth of a malignant tumor using a natural product-derived compound, or a derivative thereof, in an easy-to-formulate form.
[0014] Another aspect of the present invention is to improve the bioavailability of betulinic acid and betulinic acid derivatives in an individual by administering a therapeutically effective amount of a prodrug of betulinic acid or betulinic acid derivative to an individual in need thereof.
[0016] Yet another aspect of the present invention is to overcome the problem of high mammalian toxicity associated with synthetic anticancer agents by using a natural product-derived compound, e.g., a prodrug of betulinic acid or a betulinic acid derivative.

Problems solved by technology

The physiochemical properties of betulinic acid, e.g., a high melting point and limited solubility in hydrophilic and hydrophobic solvents, make it difficult to produce betulinic acid-containing pharmacological formulations.

Method used

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  • Method of preparing and use of prodrugs of betulinic acid derivatives
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  • Method of preparing and use of prodrugs of betulinic acid derivatives

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Embodiment Construction

[0029] Betulinic acid, 3β-hydroxy-lup-20(29)-ene-28-oic acid, is a natural, pentacyclic triterpene product isolated from several genus of higher plants. Betulinic acid has demonstrated remarkable selective antitumor activity against human melanoma (E. Pisha et al., Nature Medicine, 1, pp. 1046-1051 (1995)) and anti-HIV activity (T. Fujioka et al., J. Nat. Prod., 57, pp. 243-247 (1994)).

[0030] Through a bioassay-directed fractionation of the stem bark of Ziziphus mauritiana Lam. (Rhamnaceae), betulinic acid was isolated as an active compound that showed a cytotoxicity against cultured human melanoma cells. Betulinic acid was found to be an excellent antitumor compound against human melanoma due to its unique in vitro and in vivo cytotoxicity profile. Betulinic acid showed a strong selective antitumor activity against melanoma by induction of apoptosis.

[0031] Betulinic acid also was found to have activity against the other cancer cell lines that were tested. The cytotoxicity of betu...

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Abstract

A composition and method of preventing or inhibiting tumor growth and, more particularly, of treating a malignant tumor, using prodrugs of plant-derived compounds and derivatives is disclosed. In the method, a composition containing betulinic acid or a betulinic acid derivative is administered in a prodrug form to release betulinic acid or a betulinic acid derivative in vivo at the tumor site.

Description

CROSS REFERENCE TO RELATED APPLICATION [0001] This application claims the benefit of U.S. provisional patent application No. 60 / 226,536, filed Aug. 18, 2000.FIELD OF THE INVENTION [0002] The present invention relates to compositions and methods of inhibiting tumors and, more particularly, of treating a malignant tumor, like a melanoma, using plant-derived compounds and derivatives thereof, and in particular, prodrugs of betulinic acid and betulinic acid derivatives. BACKGROUND OF THE INVENTION [0003] Over the past four decades the incidence of melanoma has been increasing at a higher rate than any other type of cancer. It is now theorized that one in ninety American Caucasians will develop malignant melanoma in their lifetime. While an increasing proportion of melanomas are diagnosed sufficiently early to respond to surgical treatment and achieve a greater than 90% ten-year survival rate, it is estimated that nearly 7,000 individuals suffering from metastatic melanoma will die in th...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/56A61K31/565A61KA61PA61P1/00A61P1/02A61P11/00A61P13/08A61P15/00A61P17/00A61P21/00A61P25/00A61P31/18A61P35/00C07B53/00C07B61/00C07JC07J1/00C07J63/00
CPCA61K31/56C07J63/008C07J1/00A61P1/00A61P1/02A61P11/00A61P13/08A61P15/00A61P17/00A61P21/00A61P25/00A61P31/18A61P35/00
Inventor PEZZUTO, JOHN M.KOSMEDER, JEROME W. IIXU, ZE-QIZHOU, NIAN E.GOLDSMITH, MIRIAM ELAINE
Owner THE BOARD OF TRUSTEES OF THE UNIV OF ILLINOIS
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