Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity
Нема приказа
Аутори
Opsenica, Dejan M.Pocsfalvi, G
Juranić, Z.
Tinant, B
Declercq, JP
Kyle, DE
Milhous, WK
Šolaja, Bogdan A.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Извор:
Journal of Medicinal Chemistry, 2000, 43, 17, 3274-3282Издавач:
- Amer Chemical Soc, Washington
DOI: 10.1021/jm000952f
ISSN: 0022-2623
PubMed: 10966746
WoS: 000089023700010
Scopus: 2-s2.0-0034710713
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - 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 . .