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Ferrer-Casal, M.; Li, C.; Galizzi, M.; Stortz, C.A.; Szajnman, S.H.; Docampo, R.; Moreno, S.N.J.; Rodriguez, J.B. "New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase" (2014) Bioorganic and Medicinal Chemistry. 22(1):398-405
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Abstract:

As part of our project pointed at the search of new antiparasitic agents against American trypanosomiasis (Chagas disease) and toxoplasmosis a series of 2-alkylaminoethyl-1-hydroxy-1,1-bisphosphonic acids has been designed, synthesized and biologically evaluated against the etiologic agents of these parasitic diseases, Trypanosoma cruzi and Toxoplasma gondii, respectively, and also towards their target enzymes, T. cruzi and T. gondii farnesyl pyrophosphate synthase (FPPS), respectively. Surprisingly, while most pharmacologically active bisphosphonates have a hydroxyl group at the C-1 position, the additional presence of an amino group at C-3 resulted in decreased activity towards either T. cruzi cells or TcFPPS. Density functional theory calculations justify this unexpected behavior. Although these compounds were devoid of activity against T. cruzi cells and TcFPPS, they were efficient growth inhibitors of tachyzoites of T. gondii. This activity was associated with a potent inhibition of the enzymatic activity of TgFPPS. Compound 28 arises as a main example of this family of compounds exhibiting an ED50 value of 4.7 μM against tachyzoites of T. gondii and an IC50 of 0.051 μM against TgFPPS. © 2013 Published by Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase
Autor:Ferrer-Casal, M.; Li, C.; Galizzi, M.; Stortz, C.A.; Szajnman, S.H.; Docampo, R.; Moreno, S.N.J.; Rodriguez, J.B.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EHA Buenos Aires, Argentina
Center for Tropical and Emerging Global Diseases, Department of Cellular Biology, University of Georgia, Athens, GA 30602, United States
Departamento de Química Orgánica and CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EHA Buenos Aires, Argentina
Palabras clave:Antiparasitic agents; Bisphosphonates; Farnesyl pyrophosphate synthase; Toxoplasma gondii; Trypanosoma cruzi; 1 [(n alkylamino)ethyl] 1 hydroxy 1,1 bisphosphonic acid; 1 [(n decylamino)ethyl] 1 hydroxy 1,1 bisphosphonic acid; 1 [(n heptylamino)ethyl] 1 hydroxy 1,1 bisphosphonic acid; 1 [(n hexylamino)ethyl] 1 hydroxy 1,1 bisphosphonic acid; 1 [(n octylamino)ethyl] 1 hydroxy 1,1 bisphosphonic acid; 1 [(n pentylamino)ethyl] 1 hydroxy 1,1 bisphosphonic acid; 2 (decylamino)acetic acid; 2 (hexylamino)acetic acid; 2 (n heptylamino)acetic acid; 2 (n pentylamino)acetic acid; 2 (octylamino)acetic acid; 2 alkylaminoethyl 1 hydroxy 1,1 bisphosphonic acid derivative; benznidazole; bisphosphonic acid derivative; geranyltransferase; risedronic acid; unclassified drug; article; binding site; controlled study; density functional theory; drug activity; drug conformation; drug potency; drug screening; drug structure; drug synthesis; growth inhibition; hydrogen bond; Leishmania donovani; molecular recognition; nonhuman; Plasmodium falciparum; Toxoplasma gondii; Trypanosoma cruzi; Toxoplasma gondii; Trypanosoma cruzi; Antiparasitic agents; Bisphosphonates; Farnesyl pyrophosphate synthase; Toxoplasma gondii; Trypanosoma cruzi; Antiparasitic Agents; Diphosphonates; Drug Design; Geranyltranstransferase; Structure-Activity Relationship; Toxoplasma; Trypanosoma cruzi
Año:2014
Volumen:22
Número:1
Página de inicio:398
Página de fin:405
DOI: http://dx.doi.org/10.1016/j.bmc.2013.11.010
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:benznidazole, 22994-85-0; geranyltransferase, 37277-79-5, 50812-36-7; risedronic acid, 105462-24-6, 122458-82-6
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v22_n1_p398_FerrerCasal

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Citas:

---------- APA ----------
Ferrer-Casal, M., Li, C., Galizzi, M., Stortz, C.A., Szajnman, S.H., Docampo, R., Moreno, S.N.J.,..., Rodriguez, J.B. (2014) . New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase. Bioorganic and Medicinal Chemistry, 22(1), 398-405.
http://dx.doi.org/10.1016/j.bmc.2013.11.010
---------- CHICAGO ----------
Ferrer-Casal, M., Li, C., Galizzi, M., Stortz, C.A., Szajnman, S.H., Docampo, R., et al. "New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase" . Bioorganic and Medicinal Chemistry 22, no. 1 (2014) : 398-405.
http://dx.doi.org/10.1016/j.bmc.2013.11.010
---------- MLA ----------
Ferrer-Casal, M., Li, C., Galizzi, M., Stortz, C.A., Szajnman, S.H., Docampo, R., et al. "New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase" . Bioorganic and Medicinal Chemistry, vol. 22, no. 1, 2014, pp. 398-405.
http://dx.doi.org/10.1016/j.bmc.2013.11.010
---------- VANCOUVER ----------
Ferrer-Casal, M., Li, C., Galizzi, M., Stortz, C.A., Szajnman, S.H., Docampo, R., et al. New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase. Bioorg. Med. Chem. 2014;22(1):398-405.
http://dx.doi.org/10.1016/j.bmc.2013.11.010