TY  - JOUR
AU  - Opsenica, Dejan M.
AU  - Pocsfalvi, G
AU  - Juranić, Z.
AU  - Tinant, B
AU  - Declercq, JP
AU  - Kyle, DE
AU  - Milhous, WK
AU  - Šolaja, Bogdan A.
PY  - 2000
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/441
AB  - Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be similar to 2 times as active as the trans against Plasmodium falciparum DG and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity
VL  - 43
IS  - 17
SP  - 3274
EP  - 3282
DO  - 10.1021/jm000952f
ER  - 

@article{
author = "Opsenica, Dejan M. and Pocsfalvi, G and Juranić, Z. and Tinant, B and Declercq, JP and Kyle, DE and Milhous, WK and Šolaja, Bogdan A.",
year = "2000",
abstract = "Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be similar to 2 times as active as the trans against Plasmodium falciparum DG and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity",
volume = "43",
number = "17",
pages = "3274-3282",
doi = "10.1021/jm000952f"
}

Opsenica, D. M., Pocsfalvi, G., Juranić, Z., Tinant, B., Declercq, J., Kyle, D., Milhous, W.,& Šolaja, B. A.. (2000). Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 43(17), 3274-3282.
https://doi.org/10.1021/jm000952f

Opsenica DM, Pocsfalvi G, Juranić Z, Tinant B, Declercq J, Kyle D, Milhous W, Šolaja BA. Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry. 2000;43(17):3274-3282.
doi:10.1021/jm000952f .

Opsenica, Dejan M., Pocsfalvi, G, Juranić, Z., Tinant, B, Declercq, JP, Kyle, DE, Milhous, WK, Šolaja, Bogdan A., "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity" in Journal of Medicinal Chemistry, 43, no. 17 (2000):3274-3282,
https://doi.org/10.1021/jm000952f . .

TY  - JOUR
AU  - Todorović, Nevena M.
AU  - Stefanović, Milutin
AU  - Tinant, B
AU  - Declercq, JP
AU  - Makler, MT
AU  - Šolaja, Bogdan A.
PY  - 1996
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2582
AB  - Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5 alpha- and 5 beta-cholestan-3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5 beta-cholestane-3 alpha,3 beta-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (W2) malaria clones. All compounds were inactive to both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC50 = 155 nM. (C) 1996 by Elsevier Science Inc.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity
VL  - 61
IS  - 12
SP  - 688
EP  - 696
DO  - 10.1016/S0039-128X(96)00203-6
ER  - 

@article{
author = "Todorović, Nevena M. and Stefanović, Milutin and Tinant, B and Declercq, JP and Makler, MT and Šolaja, Bogdan A.",
year = "1996",
abstract = "Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5 alpha- and 5 beta-cholestan-3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5 beta-cholestane-3 alpha,3 beta-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (W2) malaria clones. All compounds were inactive to both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC50 = 155 nM. (C) 1996 by Elsevier Science Inc.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity",
volume = "61",
number = "12",
pages = "688-696",
doi = "10.1016/S0039-128X(96)00203-6"
}

Todorović, N. M., Stefanović, M., Tinant, B., Declercq, J., Makler, M.,& Šolaja, B. A.. (1996). Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. in Steroids
Elsevier Science Inc, New York., 61(12), 688-696.
https://doi.org/10.1016/S0039-128X(96)00203-6

Todorović NM, Stefanović M, Tinant B, Declercq J, Makler M, Šolaja BA. Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. in Steroids. 1996;61(12):688-696.
doi:10.1016/S0039-128X(96)00203-6 .

Todorović, Nevena M., Stefanović, Milutin, Tinant, B, Declercq, JP, Makler, MT, Šolaja, Bogdan A., "Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity" in Steroids, 61, no. 12 (1996):688-696,
https://doi.org/10.1016/S0039-128X(96)00203-6 . .