Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii

Melissa D'Ascenzio; Bruna Bizzarri; Celeste De Monte; Simone Carradori; Adriana Bolasco; Daniela Secci; Daniela Rivanera; Nathan Faulhaber; Claudia Bordón; Lorraine Jones-Brando

doi:10.1016/j.ejmech.2014.08.046

Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii

Melissa D'Ascenzio, Bruna Bizzarri, Celeste De Monte, Simone Carradori, Adriana Bolasco, Daniela Secci, Daniela Rivanera, Nathan Faulhaber, Claudia Bordón, Lorraine Jones-Brando

School of Medicine

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition.

Original language	English (US)
Pages (from-to)	17-30
Number of pages	14
Journal	European Journal of Medicinal Chemistry
Volume	86
DOIs	https://doi.org/10.1016/j.ejmech.2014.08.046
State	Published - Aug 19 2014

Keywords

Cytotoxicity
Host cell invasion
Parasite growth inhibition
Thiazolidin-4-one
Toxoplasma

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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D'Ascenzio, M., Bizzarri, B., De Monte, C., Carradori, S., Bolasco, A., Secci, D., Rivanera, D., Faulhaber, N., Bordón, C., & Jones-Brando, L. (2014). Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii. European Journal of Medicinal Chemistry, 86, 17-30. https://doi.org/10.1016/j.ejmech.2014.08.046

D'Ascenzio, M, Bizzarri, B, De Monte, C, Carradori, S, Bolasco, A, Secci, D, Rivanera, D, Faulhaber, N, Bordón, C & Jones-Brando, L 2014, 'Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii', European Journal of Medicinal Chemistry, vol. 86, pp. 17-30. https://doi.org/10.1016/j.ejmech.2014.08.046

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title = "Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii",

abstract = "We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition.",

keywords = "Cytotoxicity, Host cell invasion, Parasite growth inhibition, Thiazolidin-4-one, Toxoplasma",

author = "Melissa D'Ascenzio and Bruna Bizzarri and {De Monte}, Celeste and Simone Carradori and Adriana Bolasco and Daniela Secci and Daniela Rivanera and Nathan Faulhaber and Claudia Bord{\'o}n and Lorraine Jones-Brando",

note = "Funding Information: This work was supported by Filas (research project n° ASR2, Regione Lazio, Italy) and the Stanley Medical Research Institute. ",

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doi = "10.1016/j.ejmech.2014.08.046",

language = "English (US)",

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AU - D'Ascenzio, Melissa

AU - Bizzarri, Bruna

AU - De Monte, Celeste

AU - Carradori, Simone

AU - Bolasco, Adriana

AU - Secci, Daniela

AU - Rivanera, Daniela

AU - Faulhaber, Nathan

AU - Bordón, Claudia

AU - Jones-Brando, Lorraine

N1 - Funding Information: This work was supported by Filas (research project n° ASR2, Regione Lazio, Italy) and the Stanley Medical Research Institute.

PY - 2014/8/19

Y1 - 2014/8/19

N2 - We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition.

AB - We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition.

KW - Cytotoxicity

KW - Host cell invasion

KW - Parasite growth inhibition

KW - Thiazolidin-4-one

KW - Toxoplasma

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ER -

Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii

Abstract

Keywords

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