Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 13, 2003, Pages 2761-2768

  Opsenica, Dejan ^a   Angelovski, Goran ^b,f   Pocsfalvi, Gabriella ^c   Juranić, Zorica ^d   Žižak, Željko ^d   Kyle, Dennis ^e   Milhous, Wilbur K ^e   Šolaja, Bogdan A ^b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c CNR   (Italy)

^d National Cancer Research Institute   (Yugoslavia)

^e WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^f TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYCLOHEXANE DERIVATIVE; TETRAOXANE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CYTOTOXICITY; DRUG SYNTHESIS; HELA CELL; MICROSCOPY; NONHUMAN; PLASMODIUM FALCIPARUM;

PLASMODIUM FALCIPARUM;

EID: 0037871977     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00224-4     Document Type: Article

References (25)

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3. Selected references: (a) Lin A.J., Klayman D.L., Milhous W.K. J. Med. Chem. 30:1987;2147 (b) Nga T.T., Menage C., Beque J.-P., Bonnet-Delpon D., Gantier J.-C., Pradines B., Doury J.-C., Thac T.D. J. Med. Chem. 41:1998;4101 (c) Lin A.J., Miller R.E. J. Med. Chem. 38:1995;764 (d) Posner G.H., Parker M.H., Northorp J., Elias J.S., Ploypradith P., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;300 (e) Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.-W., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;4275 (f) Mekonnen B., Weiss E., Katz E., Ma J., Ziffer H., Kyle D.E. Bioorg. Med. Chem. 8:2000;1111 (g) O'Neill P.M., Miller A., Bishop P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., Park B.K. J. Med. Chem. 44:2001;58 (h) Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. J. Med. Chem. 44:2001;3054.
4. Selected references: (a) Lin A.J., Klayman D.L., Milhous W.K. J. Med. Chem. 30:1987;2147 (b) Nga T.T., Menage C., Beque J.-P., Bonnet-Delpon D., Gantier J.-C., Pradines B., Doury J.-C., Thac T.D. J. Med. Chem. 41:1998;4101 (c) Lin A.J., Miller R.E. J. Med. Chem. 38:1995;764 (d) Posner G.H., Parker M.H., Northorp J., Elias J.S., Ploypradith P., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;300 (e) Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.-W., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;4275 (f) Mekonnen B., Weiss E., Katz E., Ma J., Ziffer H., Kyle D.E. Bioorg. Med. Chem. 8:2000;1111 (g) O'Neill P.M., Miller A., Bishop P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., Park B.K. J. Med. Chem. 44:2001;58 (h) Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. J. Med. Chem. 44:2001;3054.
5. Selected references: (a) Lin A.J., Klayman D.L., Milhous W.K. J. Med. Chem. 30:1987;2147 (b) Nga T.T., Menage C., Beque J.-P., Bonnet-Delpon D., Gantier J.-C., Pradines B., Doury J.-C., Thac T.D. J. Med. Chem. 41:1998;4101 (c) Lin A.J., Miller R.E. J. Med. Chem. 38:1995;764 (d) Posner G.H., Parker M.H., Northorp J., Elias J.S., Ploypradith P., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;300 (e) Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.-W., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;4275 (f) Mekonnen B., Weiss E., Katz E., Ma J., Ziffer H., Kyle D.E. Bioorg. Med. Chem. 8:2000;1111 (g) O'Neill P.M., Miller A., Bishop P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., Park B.K. J. Med. Chem. 44:2001;58 (h) Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. J. Med. Chem. 44:2001;3054.
6. Selected references: (a) Lin A.J., Klayman D.L., Milhous W.K. J. Med. Chem. 30:1987;2147 (b) Nga T.T., Menage C., Beque J.-P., Bonnet-Delpon D., Gantier J.-C., Pradines B., Doury J.-C., Thac T.D. J. Med. Chem. 41:1998;4101 (c) Lin A.J., Miller R.E. J. Med. Chem. 38:1995;764 (d) Posner G.H., Parker M.H., Northorp J., Elias J.S., Ploypradith P., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;300 (e) Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.-W., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;4275 (f) Mekonnen B., Weiss E., Katz E., Ma J., Ziffer H., Kyle D.E. Bioorg. Med. Chem. 8:2000;1111 (g) O'Neill P.M., Miller A., Bishop P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., Park B.K. J. Med. Chem. 44:2001;58 (h) Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. J. Med. Chem. 44:2001;3054.
7. Selected references: (a) Lin A.J., Klayman D.L., Milhous W.K. J. Med. Chem. 30:1987;2147 (b) Nga T.T., Menage C., Beque J.-P., Bonnet-Delpon D., Gantier J.-C., Pradines B., Doury J.-C., Thac T.D. J. Med. Chem. 41:1998;4101 (c) Lin A.J., Miller R.E. J. Med. Chem. 38:1995;764 (d) Posner G.H., Parker M.H., Northorp J., Elias J.S., Ploypradith P., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;300 (e) Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.-W., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;4275 (f) Mekonnen B., Weiss E., Katz E., Ma J., Ziffer H., Kyle D.E. Bioorg. Med. Chem. 8:2000;1111 (g) O'Neill P.M., Miller A., Bishop P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., Park B.K. J. Med. Chem. 44:2001;58 (h) Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. J. Med. Chem. 44:2001;3054.
8. Selected references: (a) Lin A.J., Klayman D.L., Milhous W.K. J. Med. Chem. 30:1987;2147 (b) Nga T.T., Menage C., Beque J.-P., Bonnet-Delpon D., Gantier J.-C., Pradines B., Doury J.-C., Thac T.D. J. Med. Chem. 41:1998;4101 (c) Lin A.J., Miller R.E. J. Med. Chem. 38:1995;764 (d) Posner G.H., Parker M.H., Northorp J., Elias J.S., Ploypradith P., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;300 (e) Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.-W., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;4275 (f) Mekonnen B., Weiss E., Katz E., Ma J., Ziffer H., Kyle D.E. Bioorg. Med. Chem. 8:2000;1111 (g) O'Neill P.M., Miller A., Bishop P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., Park B.K. J. Med. Chem. 44:2001;58 (h) Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. J. Med. Chem. 44:2001;3054.
9. Selected references: (a) Lin A.J., Klayman D.L., Milhous W.K. J. Med. Chem. 30:1987;2147 (b) Nga T.T., Menage C., Beque J.-P., Bonnet-Delpon D., Gantier J.-C., Pradines B., Doury J.-C., Thac T.D. J. Med. Chem. 41:1998;4101 (c) Lin A.J., Miller R.E. J. Med. Chem. 38:1995;764 (d) Posner G.H., Parker M.H., Northorp J., Elias J.S., Ploypradith P., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;300 (e) Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.-W., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S., Shapiro T.A. J. Med. Chem. 42:1999;4275 (f) Mekonnen B., Weiss E., Katz E., Ma J., Ziffer H., Kyle D.E. Bioorg. Med. Chem. 8:2000;1111 (g) O'Neill P.M., Miller A., Bishop P.D., Hindley S., Maggs J.L., Ward S.A., Roberts S.M., Scheinmann F., Stachulski A.V., Posner G.H., Park B.K. J. Med. Chem. 44:2001;58 (h) Posner G.H., Jeon H.B., Parker M.H., Krasavin M., Paik I.-H., Shapiro T.A. J. Med. Chem. 44:2001;3054.
10. (a) Dong Y., Matile H., Chollet J., Kaminsky R., Wood J.K., Vennerstrom J.L. J. Med. Chem. 42:1999;1477 (b) McCullogh K.J., Wood J.K., Bhattacharjee A.K., Dong Y., Kyle D.E., Milhous W.K., Vennerstrom J.L. J. Med. Chem. 43:2000;1246 (c) Vennerstrom J.L., Dong Y., Andersen S.L., Ager A.L. Jr., Fu H.-N., Miller R.E., Wesche D.L., Kyle D.E., Gerena L., Walters S.M., Wood J.K., Edwards G., Holme A.D., McLean W.G., Milhous W.K. J. Med. Chem. 43:2000;2753. and references cited therein (d) Vennerstrom J.L., Ager A.L., Andersen S.L., Grace J.M., Wongpanich V., Angerhofer C.K., Hu J.K., Wesche D.L. Am. J. Trop. Med. Hyg. 62:2000;573 (e) Jefford C.W., Rossier J.-C., Milhous W.K. Heterocycles. 52:2000;1345 (f) Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., McCullough K.J. J. Med. Chem. 44:2001;2357.
11. (a) Dong Y., Matile H., Chollet J., Kaminsky R., Wood J.K., Vennerstrom J.L. J. Med. Chem. 42:1999;1477 (b) McCullogh K.J., Wood J.K., Bhattacharjee A.K., Dong Y., Kyle D.E., Milhous W.K., Vennerstrom J.L. J. Med. Chem. 43:2000;1246 (c) Vennerstrom J.L., Dong Y., Andersen S.L., Ager A.L. Jr., Fu H.-N., Miller R.E., Wesche D.L., Kyle D.E., Gerena L., Walters S.M., Wood J.K., Edwards G., Holme A.D., McLean W.G., Milhous W.K. J. Med. Chem. 43:2000;2753. and references cited therein (d) Vennerstrom J.L., Ager A.L., Andersen S.L., Grace J.M., Wongpanich V., Angerhofer C.K., Hu J.K., Wesche D.L. Am. J. Trop. Med. Hyg. 62:2000;573 (e) Jefford C.W., Rossier J.-C., Milhous W.K. Heterocycles. 52:2000;1345 (f) Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., McCullough K.J. J. Med. Chem. 44:2001;2357.
12. (a) Dong Y., Matile H., Chollet J., Kaminsky R., Wood J.K., Vennerstrom J.L. J. Med. Chem. 42:1999;1477 (b) McCullogh K.J., Wood J.K., Bhattacharjee A.K., Dong Y., Kyle D.E., Milhous W.K., Vennerstrom J.L. J. Med. Chem. 43:2000;1246 (c) Vennerstrom J.L., Dong Y., Andersen S.L., Ager A.L. Jr., Fu H.-N., Miller R.E., Wesche D.L., Kyle D.E., Gerena L., Walters S.M., Wood J.K., Edwards G., Holme A.D., McLean W.G., Milhous W.K. J. Med. Chem. 43:2000;2753. and references cited therein (d) Vennerstrom J.L., Ager A.L., Andersen S.L., Grace J.M., Wongpanich V., Angerhofer C.K., Hu J.K., Wesche D.L. Am. J. Trop. Med. Hyg. 62:2000;573 (e) Jefford C.W., Rossier J.-C., Milhous W.K. Heterocycles. 52:2000;1345 (f) Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., McCullough K.J. J. Med. Chem. 44:2001;2357.
13. (a) Dong Y., Matile H., Chollet J., Kaminsky R., Wood J.K., Vennerstrom J.L. J. Med. Chem. 42:1999;1477 (b) McCullogh K.J., Wood J.K., Bhattacharjee A.K., Dong Y., Kyle D.E., Milhous W.K., Vennerstrom J.L. J. Med. Chem. 43:2000;1246 (c) Vennerstrom J.L., Dong Y., Andersen S.L., Ager A.L. Jr., Fu H.-N., Miller R.E., Wesche D.L., Kyle D.E., Gerena L., Walters S.M., Wood J.K., Edwards G., Holme A.D., McLean W.G., Milhous W.K. J. Med. Chem. 43:2000;2753. and references cited therein (d) Vennerstrom J.L., Ager A.L., Andersen S.L., Grace J.M., Wongpanich V., Angerhofer C.K., Hu J.K., Wesche D.L. Am. J. Trop. Med. Hyg. 62:2000;573 (e) Jefford C.W., Rossier J.-C., Milhous W.K. Heterocycles. 52:2000;1345 (f) Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., McCullough K.J. J. Med. Chem. 44:2001;2357.
14. (a) Dong Y., Matile H., Chollet J., Kaminsky R., Wood J.K., Vennerstrom J.L. J. Med. Chem. 42:1999;1477 (b) McCullogh K.J., Wood J.K., Bhattacharjee A.K., Dong Y., Kyle D.E., Milhous W.K., Vennerstrom J.L. J. Med. Chem. 43:2000;1246 (c) Vennerstrom J.L., Dong Y., Andersen S.L., Ager A.L. Jr., Fu H.-N., Miller R.E., Wesche D.L., Kyle D.E., Gerena L., Walters S.M., Wood J.K., Edwards G., Holme A.D., McLean W.G., Milhous W.K. J. Med. Chem. 43:2000;2753. and references cited therein (d) Vennerstrom J.L., Ager A.L., Andersen S.L., Grace J.M., Wongpanich V., Angerhofer C.K., Hu J.K., Wesche D.L. Am. J. Trop. Med. Hyg. 62:2000;573 (e) Jefford C.W., Rossier J.-C., Milhous W.K. Heterocycles. 52:2000;1345 (f) Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., McCullough K.J. J. Med. Chem. 44:2001;2357.
15. (a) Dong Y., Matile H., Chollet J., Kaminsky R., Wood J.K., Vennerstrom J.L. J. Med. Chem. 42:1999;1477 (b) McCullogh K.J., Wood J.K., Bhattacharjee A.K., Dong Y., Kyle D.E., Milhous W.K., Vennerstrom J.L. J. Med. Chem. 43:2000;1246 (c) Vennerstrom J.L., Dong Y., Andersen S.L., Ager A.L. Jr., Fu H.-N., Miller R.E., Wesche D.L., Kyle D.E., Gerena L., Walters S.M., Wood J.K., Edwards G., Holme A.D., McLean W.G., Milhous W.K. J. Med. Chem. 43:2000;2753. and references cited therein (d) Vennerstrom J.L., Ager A.L., Andersen S.L., Grace J.M., Wongpanich V., Angerhofer C.K., Hu J.K., Wesche D.L. Am. J. Trop. Med. Hyg. 62:2000;573 (e) Jefford C.W., Rossier J.-C., Milhous W.K. Heterocycles. 52:2000;1345 (f) Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., McCullough K.J. J. Med. Chem. 44:2001;2357.
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22. For comparison, the average GI50, TGI and LC50 values of well-known cytostatic cis-platinum (NSC 119875) for cell lines given in Table 4 are 3.31, 26.26 and 424.56 (μM), respectively. For further details see: http://dtp.nci.nih.gov/docs/static_pages/compounds/119875.html.
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