Synthesis, Characterization, and Antimalarial Activity of the Glucuronides of the Hydroxylated Metabolites of Arteether

Journal of Medicinal Chemistry

Volumn 38, Issue 11, 1995, Pages 1911-1921

  Ramu, Kumar ^a   Baker, John K ^b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b ALCON RESEARCH LTD   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTEETHER; ARTEMISININ; DIHYDROARTEMISININ; DRUG METABOLITE; GLUCURONIDE;

ANTIMALARIAL ACTIVITY; ARTICLE; BRAIN MALARIA; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG HYDROXYLATION; DRUG SOLUBILITY; DRUG SYNTHESIS; DRUG TRANSFORMATION; FERMENTATION; LIVER MICROSOME; MALARIA FALCIPARUM; MOLECULAR MODEL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLASMODIUM FALCIPARUM; STEREOCHEMISTRY; STREPTOMYCES LAVENDULAE;

ANIMAL; ANTIMALARIALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMPARATIVE STUDY; GLUCURONATES; HYDROLYSIS; HYDROXYLATION; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; PLASMODIUM FALCIPARUM; SESQUITERPENES; STEREOISOMERISM; SUPPORT, NON-U.S. GOV'T;

EID: 0029071407     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00011a011     Document Type: Article

References (33)

1. Klayman, D. L.; et al. Isolation of Artemisinin (Qinghaosu) from Artemisia Annua Growing in the United States. J. Nat. Prod. 1984, 47, 715-717.
2. Li, G. Q.; Guo, X. B.; Jin, R.; Wang, Z. C.; Jian, H. X.; Li, Z. Y. Clinical Studies on Treatment of Cerebral Malaria with Qinghaosu and its Derivatives. J. Tradit. Chinese Med. 1982, 2, 125-130.
3. Luo, X.; Shen, C. The Chemistry, Pharmacology and Clinical Applications of Qinghaosu (Artemisinin) and its Derivatives. Med. Res. Rev. 1987, 7, 29-52.
4. China Cooperative Research Group on Quinghaosu and its Derivatives as Antimalarials. The Chemistry and Synthesis of Qinghaosu Derivatives. J. Tradit. Chinese Med. 1982, 2, 9-16.
5. Baker, J. K.; Yarber, R. H.; Hufford, C. D.; Lee, I.; ElSohly, H. N.; McChesney, J. D. Thermospray Mass Spectroscopy / High Performance Liquid Chromatographic Identification of the Metabolites formed from Arteether using a Rat Liver Microsome Preparation. Biomed. Environ. Mass Spectrom. 1988, 18, 337-351.
6. Hufford, C. D.; Lee, I.; ElSohly, H. N.; Chi, H. T.; Baker, J. K. Structure Elucidiation and Thermospray High-Performance Liquid Chromatography/Mass Spectroscopy (HPLC/MS) of the Microbial and Mammalian Metabolites of the Antimalarial Arteether. Pharm. Res. 1990, 7, 923-927.
7. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology, 1st ed.; John Wiley & Sons: New York, Chichester, Brisbane, Toronto, 1979.
8. Chi, H. T.; et al. Identification of the In Vivo Metabolites of the Antimalarial Arteether By Thermospray High-Performance Liquid Chromatography/Mass Spectrometry. Biol. Mass Spectrom. 1991, 20, 609-628.
9. Abbot, F. V.; Franklin, B. J. Morphine-6-Glucuronide Contributes to Rewarding Effects of Opiates. Life Sci. 1991, 48, 1157-1163.
10. Mattammal, M. B.; Lakshmi, V. M.; Dawley, R. M.; Zenser, T. V.; Davis, B. B.; Hsu, F. Thermospray High Performance Liquid Chromatography/Mass Spectrometric Identification of a Bladder Carcinogen Metabolite Isolated from Guinea Pig Urine. Biomed. Environ. Mass Spectrom. 1990, 19, 601-608.
11. Brossi, A.; et al. Arteether, a New Antimalarial Drug: Synthesis and Antimalarial Properties. J. Med. Chem. 1988, 31, 645-650.
12. 13C NMR Assignments of Arteethers. Spectrosc. Lett. 1987, 20, 439-444.
13. Lee, I.; ElSohly, H. N.; Hufford, C. D. Microbial Metabolism Studies of the Antimalarial Drug Arteether. Pharm. Res. 1990, 7, 199-203.
14. Kaspersen, F. M.; Van Boeckel, C. A. A. A Review of the Methods of Chemical Synthesis of Sulphate and Glucuronide Conjugates. Xenobiotica 1987, 17, 1451-1471.
15. Koenigs, W.; Knorr, E. Über einege Derivative des Traubenzuk-ers und der Galactose. (About another derivative from grape sugar and galactose.) Chem. Ber. 1901, 34, 957-981.
16. Igarashi, K. The Koenigs-Knorr reaction. Adv. Carbohyr. Chem. Biochem. 1977, 34, 243-283.
17. Conchie, J.; Lewy, G. A. [86], Methyl Glycopyranosides by the Koenigs-Knorr Method. Methods Carbohyr. Chem. 1963, 2, 332-335.
18. Gerpe, L. D.; Yeh, H. J. C.; Yu, Q.; Brossi, A.; Flippen-Anderson, J. L. C-(ll)-Epi-Deoxyarteether: Formation and Structure. Heterocycles 1988, 27, 897-901.
19. Lee, I.; ElSohly, H. N.; Croom, E. M.; Hufford, C. D. Microbial Metabolism Studies of the Antimalarial Sesquiterpene Artemisinin. J. Nat. Prod. 1989, 52, 337-341.
20. Smith, C. P.; Benet, L. Z. Characterization of the Isomeric Esters of Zomepirac Glucuronide by Proton NMR. Drug Metab. Dispos. 1986, 14, 503-505.
21. 3Jhh Coupling Measurements in the Determination of the Conformation of the Sesquiterpene Antimalarial Arteether in Solution. Spectrosc. Lett. 1990, 23, 111-122.
22. Karplus, M. Contact Electron-Spin Coupling of Nuclear Magnetic Moments. J. Chem. Phys. 1959, 30, 11.
23. Colucci, W. J.; Jungk, S. J.; Gandour, R. D. An Equation Utilizing Emperically Derived Substituent Constants in Substituted Ethanes. Magn. Reson. Chem. 1985, 23, 335.
24. Colucci, W. J.; Gandour, R. D.; Mooberry, E. A. Conformational Analysis of Charged Flexible Molecules in Water by Application of a New Karplus Equation Combined with MM2 Computations. J. Am. Chem. Soc. 1986, 108, 7141.
25. Baker, J. K.; Ma, C. Y. Retention Index Scale for Liquid-Liquid Chromatography. J. Chromatogr. 1979, 169, 107-115.
26. Baker, J. K. Estimation of High-Performance Liquid Chromatographic Retention Indices of Glucuronide Metabolites. J. Liq. Chromatogr. 1981, 4, 271-278.
27. Kar, K.; Nath, A.; Bajipai, R.; Dutta, G. P.; Vishwakarma, R. A. Pharmacology of α/β Arteether -A potential Antimalarial Drug. J. Ethnopharmacol. 1989, 27, 297-305.
28. Pravdic, N.; Keglevic, D. Glucuronic Esters. Part I. Synthesis of Methyl 2, 3, 4-Tri-O-acetyl-1-O-acyl-D-glucopyranuronates, by use of Carbodiimide. J. Chem. Soc. 1964, 4633-4635.
29. Luo, X.; Yeh, H. J. C.; Brossi, A.; Flippen-Anderson, J. L.; Gilardi, R. The Chemistry of Drugs, IV. Configurations of Antimalarials Derived from Qinghaosu: Dihydroqinghaosu, Artemether, and Artesunic Acid. Helv. Chim. Acta 1984, 67, 1515-1522.
30. Schnur, D. M.; Grieshaber, M. V.; Bowen, J. P. Development of an Internal Searching Algorithm for Parameterization of the MM2/MM3 Force Fields. J. Comput. Chem. 1991, 12, 844-849.
31. Trager, W.; Jensen, J. B. Human Malaria Parasites in Continuous Culture. Science 1976, 190, 673-675.
32. Lambros, C.; Vanderberg, J. P. Synchronization of Plasmodium faliparum erythrocytic stages in culture. J. Parasitol. 1979, 65, 418-420.
33. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative Assessment of Antimalarial Activity In Vitro by a Semi-Automated Microdilution Technique. Antimicrob. Agents Chemother. 1979, 16, 710-718.