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dc.contributor.author
Ferrer, Mariana
dc.contributor.author
Li, Catherine
dc.contributor.author
Gallizi, Melina
dc.contributor.author
Stortz, Carlos Arturo
dc.contributor.author
Szajnman, Sergio Hernan
dc.contributor.author
Docampo, Roberto
dc.contributor.author
Moreno, Silvia N. J.
dc.contributor.author
Rodriguez, Juan Bautista
dc.date.available
2016-11-14T14:36:32Z
dc.date.issued
2014-01
dc.identifier.citation
Ferrer, Mariana; Li, Catherine; Gallizi, Melina; Stortz, Carlos Arturo; Szajnman, Sergio Hernan; et al.; New Insights into Molecular Recognition of 1,1-Bisphosphonic Acids by Farnesyl Pyrophosphate Synthase; Elsevier; Bioorganic; 22; 1; 1-2014; 398-405
dc.identifier.issn
0968-0896
dc.identifier.uri
http://hdl.handle.net/11336/8177
dc.description.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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Bisphosphonic Acid
dc.subject
Recognition
dc.subject
Molecular Modeling
dc.subject.classification
Química Orgánica
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
New Insights into Molecular Recognition of 1,1-Bisphosphonic Acids by Farnesyl Pyrophosphate Synthase
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2016-11-11T15:11:37Z
dc.journal.volume
22
dc.journal.number
1
dc.journal.pagination
398-405
dc.journal.pais
Países Bajos
dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Ferrer, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
dc.description.fil
Fil: Li, Catherine. University of Georgia; Estados Unidos
dc.description.fil
Fil: Gallizi, Melina. Georgia State University; Estados Unidos
dc.description.fil
Fil: Stortz, Carlos Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
dc.description.fil
Fil: Szajnman, Sergio Hernan. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
dc.description.fil
Fil: Docampo, Roberto. University of Georgia; Estados Unidos
dc.description.fil
Fil: Moreno, Silvia N. J.. University of Georgia; Estados Unidos
dc.description.fil
Fil: Rodriguez, Juan Bautista. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
dc.journal.title
Bioorganic
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.1016/j.bmc.2013.11.010
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0968089613009413


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