Structure-activity relationship of hybrids of Cinchona alkaloids and bile acids with in vitro antiplasmodial and antitrypanosomal activities
In this work, a series of hybrid compounds were tested as antiparasitic substances. These hybrids were prepared from bile acids and a series of antiparasitic Cinchona alkaloids by the formation of a covalent C-C bond via a decarboxylative Barton-Zard reaction between the two entities. The bile acids...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
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Elsevier Masson SAS
2015
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 10664caa a22014897a 4500 | ||
|---|---|---|---|
| 001 | PAPER-13752 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204410.0 | ||
| 008 | 190411s2015 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84937208428 | |
| 024 | 7 | |2 cas |a artemisinin, 63968-64-9; camptothecin, 7689-03-4; chloroquine, 132-73-0, 3545-67-3, 50-63-5, 54-05-7; suramin, 129-46-4, 145-63-1; Antimalarials; Bile Acids and Salts; Cinchona Alkaloids; Trypanocidal Agents | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a EJMCA | ||
| 100 | 1 | |a Leverrier, A. | |
| 245 | 1 | 0 | |a Structure-activity relationship of hybrids of Cinchona alkaloids and bile acids with in vitro antiplasmodial and antitrypanosomal activities |
| 260 | |b Elsevier Masson SAS |c 2015 | ||
| 270 | 1 | 0 | |m Palermo, J.A.; UMYMFOR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. 2, Argentina |
| 506 | |2 openaire |e Política editorial | ||
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| 520 | 3 | |a In this work, a series of hybrid compounds were tested as antiparasitic substances. These hybrids were prepared from bile acids and a series of antiparasitic Cinchona alkaloids by the formation of a covalent C-C bond via a decarboxylative Barton-Zard reaction between the two entities. The bile acids showed only weak antiparasitic properties, but all the hybrids exhibited high in vitro activities (IC<inf>50</inf>: 0.48-5.39 μM) against Trypanosoma brucei. These hybrids were more active than their respective parent alkaloids (up to a 135 fold increase in activity), and displayed good selectivity indices. Aditionally, all these compounds inhibited the in vitro growth of a chloroquine-sensitive strain of Plasmodium falciparum (3D7: IC<inf>50</inf>: 36.1 nM to 8.72 μM), and the most active hybrids had IC<inf>50</inf>s comparable to that of artemisinin (IC<inf>50</inf>: 36 nM). Some structure-activity relationships among the group of 48 hybrids are discussed. The increase in antiparasitic activity may be explained by an improvement in bioavailability, since the more lipophilic derivatives showed the lowest IC<inf>50</inf>s. © 2015 Published by Elsevier Masson SAS. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Secretaría de Ciencia y Técnica, Universidad de Buenos Aires, 20020100100123 | ||
| 536 | |a Detalles de la financiación: Applied Scientific Research Fund, N° 3.4533.10 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP No. 516-2009 | ||
| 536 | |a Detalles de la financiación: Research at the University of Buenos Aires was supported by Grants from CONICET (PIP No. 516-2009 ), UBACYT ( 20020100100123 , Prog. 2011-2014), and ANPCYT ( PICT 2010-1808 ). A.L. thanks CONICET for a postdoctoral fellowship. We thank Dr. Gabriela Cabrera (UMYMFOR–CONICET) for recording the mass spectra and Eng. José Gallardo and Lic. Gernot Eskuche (UMYMFOR–CONICET) for some of the NMR spectra. This work was partly supported by the Belgian Fund for Scientific Research (grants N° 3.4533.10 , FRFC2.4555.08 and T.0190.13 ). The authors thank MINCyT (Argentina) and FNRS (Belgium) for the Bilateral Cooperation Project N° V4/325M-NR/DeM-14.702 – BE1208. Appendix A | ||
| 593 | |a UMYMFOR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. 2, Buenos Aires, 1428, Argentina | ||
| 593 | |a Pharmacognosy Research Group, Louvain Drug Research Institute, Université Catholique de Louvain, Avenue E. Mounier B1.72.03, Brussels, B-1200, Belgium | ||
| 593 | |a Laboratory of Pharmacognosy, Drug Research Center (CIRM), University of Liège, Avenue de l'Hôpital 1, B36, Liège, B-4000, Belgium | ||
| 690 | 1 | 0 | |a ANTIPARASITIC ACTIVITY |
| 690 | 1 | 0 | |a BARTON-ZARD REACTION |
| 690 | 1 | 0 | |a BILE ACIDS |
| 690 | 1 | 0 | |a CINCHONA ALKALOIDS |
| 690 | 1 | 0 | |a HYBRIDS |
| 690 | 1 | 0 | |a ARTEMISININ |
| 690 | 1 | 0 | |a BILE ACID |
| 690 | 1 | 0 | |a CAMPTOTHECIN |
| 690 | 1 | 0 | |a CHLOROQUINE |
| 690 | 1 | 0 | |a CINCHONA ALKALOID |
| 690 | 1 | 0 | |a SURAMIN |
| 690 | 1 | 0 | |a ANTIMALARIAL AGENT |
| 690 | 1 | 0 | |a ANTITRYPANOSOMAL AGENT |
| 690 | 1 | 0 | |a BILE ACID |
| 690 | 1 | 0 | |a CINCHONA ALKALOID |
| 690 | 1 | 0 | |a ANTIMALARIAL ACTIVITY |
| 690 | 1 | 0 | |a ANTIPLASMODIAL ACTIVITY |
| 690 | 1 | 0 | |a ANTIPROTOZOAL ACTIVITY |
| 690 | 1 | 0 | |a ANTITRYPANOSOMAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a DRUG BIOAVAILABILITY |
| 690 | 1 | 0 | |a DRUG CYTOTOXICITY |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a FIBROBLAST |
| 690 | 1 | 0 | |a HETERONUCLEAR MULTIPLE BOND CORRELATION |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a HUMAN CELL |
| 690 | 1 | 0 | |a HYBRID |
| 690 | 1 | 0 | |a IC50 |
| 690 | 1 | 0 | |a IN VITRO STUDY |
| 690 | 1 | 0 | |a LIPOPHILICITY |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a PLASMODIUM FALCIPARUM |
| 690 | 1 | 0 | |a STRUCTURE ACTIVITY RELATION |
| 690 | 1 | 0 | |a TRYPANOSOMA BRUCEI |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a CONFORMATION |
| 690 | 1 | 0 | |a DOSE RESPONSE |
| 690 | 1 | 0 | |a DRUG EFFECTS |
| 690 | 1 | 0 | |a DRUG SENSITIVITY |
| 690 | 1 | 0 | |a STRUCTURE ACTIVITY RELATION |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a TRYPANOSOMA BRUCEI BRUCEI |
| 690 | 1 | 0 | |a ANTIMALARIALS |
| 690 | 1 | 0 | |a BILE ACIDS AND SALTS |
| 690 | 1 | 0 | |a CINCHONA ALKALOIDS |
| 690 | 1 | 0 | |a DOSE-RESPONSE RELATIONSHIP, DRUG |
| 690 | 1 | 0 | |a MOLECULAR CONFORMATION |
| 690 | 1 | 0 | |a PARASITIC SENSITIVITY TESTS |
| 690 | 1 | 0 | |a PLASMODIUM FALCIPARUM |
| 690 | 1 | 0 | |a STRUCTURE-ACTIVITY RELATIONSHIP |
| 690 | 1 | 0 | |a TRYPANOCIDAL AGENTS |
| 690 | 1 | 0 | |a TRYPANOSOMA BRUCEI BRUCEI |
| 700 | 1 | |a Bero, J. | |
| 700 | 1 | |a Cabrera, J. | |
| 700 | 1 | |a Frédérich, M. | |
| 700 | 1 | |a Quetin-Leclercq, J. | |
| 700 | 1 | |a Palermo, J.A. | |
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