Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1- bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase
The effect of long-chain 2-alkylaminoethyl-1,1-bisphosphonates against proliferation of the clinically more relevant form of Trypanosoma cruzi, the etiologic agent of American trypanosomiasis (Chagas' disease), and against tachyzoites of Toxoplasma gondii was investigated. Particularly, compoun...
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2011
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 13093caa a22016937a 4500 | ||
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| 001 | PAPER-10687 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204045.0 | ||
| 008 | 190411s2011 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-79953227657 | |
| 024 | 7 | |2 cas |a benznidazole, 22994-85-0; geranyltransferase, 37277-79-5, 50812-36-7; Antiprotozoal Agents; Diphosphonates; Enzyme Inhibitors; Geranyltranstransferase, 2.5.1.10 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a BMECE | ||
| 100 | 1 | |a Rosso, V.S. | |
| 245 | 1 | 0 | |a Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1- bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase |
| 260 | |c 2011 | ||
| 270 | 1 | 0 | |m Rodriguez, J. B.; Departamento de Química Orgánica and UMYMFOR (CONICET-FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EHA Buenos Aires, Argentina; email: jbr@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 520 | 3 | |a The effect of long-chain 2-alkylaminoethyl-1,1-bisphosphonates against proliferation of the clinically more relevant form of Trypanosoma cruzi, the etiologic agent of American trypanosomiasis (Chagas' disease), and against tachyzoites of Toxoplasma gondii was investigated. Particularly, compound 26 proved to be an extremely potent inhibitor against the intracellular form of T. cruzi, exhibiting IC50 values at the nanomolar range. This cellular activity was associated with a strong inhibition of the enzymatic activity of T. cruzi farnesyl diphosphate synthase (TcFPPS), which constitutes a valid target for Chagas' disease chemotherapy. Compound 26 was an effective agent against T. cruzi (amastigotes) exhibiting an IC50 value of 0.67 μM, while this compound showed an IC50 value of 0.81 μM against the target enzyme TcFPPS. This drug was less effective against the enzymatic activity of T. cruzi solanesyl diphosphate synthase TcSPPS showing an IC50 value of 3.2 μM. Interestingly, compound 26 was also very effective against T. gondii (tachyzoites) exhibiting IC50 values of 6.23 μM. This cellular activity was also related to the inhibition of the enzymatic activity towards the target enzyme TgFPPS (IC50 = 0.093 μM) As bisphosphonate- containing compounds are FDA-approved drugs for the treatment of bone resorption disorders, their potential low toxicity makes them good candidates to control different tropical diseases. © 2011 Elsevier Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: National Council for Scientific Research, PIP 1888 | ||
| 536 | |a Detalles de la financiación: Foundation for the National Institutes of Health, AI-068467, AI-082542 | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, X-191 | ||
| 536 | |a Detalles de la financiación: Ellison Medical Foundation | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 2008 #1690 | ||
| 536 | |a Detalles de la financiación: We thank Allysa Smith for help with T. gondii cultures. This work was supported by Grants from the National Research Council of Argentina ( PIP 1888 ), ANPCyT ( PICT 2008 #1690 ), and the Universidad de Buenos Aires ( X-191 ) to J.B.R., and the U.S. National Institutes of Health to R.D. ( AI-082542 ) and S.N.J.M. ( AI-068467 ). V.S.R. was supported in part by a training grant of the Ellison Medical Foundation to the Center for Tropical and Emerging Global Diseases. | ||
| 593 | |a Departamento de Química Orgánica and UMYMFOR (CONICET-FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EHA Buenos Aires, Argentina | ||
| 593 | |a Center for Tropical and Emerging Global Diseases, Department of Cellular Biology, University of Georgia, Athens, GA 30602, United States | ||
| 690 | 1 | 0 | |a CHAGAS' DISEASE |
| 690 | 1 | 0 | |a FARNESYL PYROPHOSPHATE SYNTHASE |
| 690 | 1 | 0 | |a TOXOPLASMA GONDII |
| 690 | 1 | 0 | |a TOXOPLASMOSIS |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a 1 (2 ALKYLAMINOETHYL) 1,1 BISPHOSPHONIC ACID DERIVATIVE |
| 690 | 1 | 0 | |a 1 [(BENZYLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a 1 [(N DEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a 1 [(N DODEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a 1 [(N HEXADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a 1 [(N NON 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a 1 [(N OCTADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a 1 [(N TETRADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a 1 [(N UNDEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID |
| 690 | 1 | 0 | |a ANTIPROTOZOAL AGENT |
| 690 | 1 | 0 | |a BENZNIDAZOLE |
| 690 | 1 | 0 | |a GERANYLTRANSFERASE |
| 690 | 1 | 0 | |a MICROORGANISM PROTEIN |
| 690 | 1 | 0 | |a OCTAPRENYLTRANSFERASE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(BENZYLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(N DEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(N DODEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(N HEXADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(N NON 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(N OCTADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(N TETRADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a TETRAETHYL 1 [(N UNDEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a AMASTIGOTE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHAGAS DISEASE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a DRUG SCREENING |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a DRUG TARGETING |
| 690 | 1 | 0 | |a ENZYME ACTIVITY |
| 690 | 1 | 0 | |a ENZYME INHIBITION |
| 690 | 1 | 0 | |a IC 50 |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a TACHYZOITE |
| 690 | 1 | 0 | |a TOXOPLASMA GONDII |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a ANTIPROTOZOAL AGENTS |
| 690 | 1 | 0 | |a CERCOPITHECUS AETHIOPS |
| 690 | 1 | 0 | |a DIPHOSPHONATES |
| 690 | 1 | 0 | |a ENZYME INHIBITORS |
| 690 | 1 | 0 | |a GERANYLTRANSTRANSFERASE |
| 690 | 1 | 0 | |a MOLECULAR TARGETED THERAPY |
| 690 | 1 | 0 | |a STRUCTURE-ACTIVITY RELATIONSHIP |
| 690 | 1 | 0 | |a TOXOPLASMA |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a VERO CELLS |
| 690 | 1 | 0 | |a TOXOPLASMA GONDII |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 700 | 1 | |a Szajnman, S.H. | |
| 700 | 1 | |a Malayil, L. | |
| 700 | 1 | |a Galizzi, M. | |
| 700 | 1 | |a Moreno, S.N.J. | |
| 700 | 1 | |a Docampo, R. | |
| 700 | 1 | |a Rodriguez, J.B. | |
| 773 | 0 | |d 2011 |g v. 19 |h pp. 2211-2217 |k n. 7 |p Bioorg. Med. Chem. |x 09680896 |w (AR-BaUEN)CENRE-3989 |t Bioorganic and Medicinal Chemistry | |
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| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_09680896_v19_n7_p2211_Rosso |y Handle |
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