Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties

Mehdi Zaghouani; Oscar Gayraud; Vincent Jactel; Sébastien Prévost; Ambre Dezaire; Michèle Sabbah; Alexandre Escargueil; Thanh Lan Lai; Christophe Le Clainche; Nathalie Rocques; Stéphane Romero; Alexis Gautreau; Florent Blanchard; Gilles Frison; Bastien Nay

doi:10.1002/chem.201804023

Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties

Mehdi Zaghouani
, Oscar Gayraud
, Vincent Jactel
, Sébastien Prévost
, Ambre Dezaire
, Michèle Sabbah
, Alexandre Escargueil
, Thanh Lan Lai
, Christophe Le Clainche
, Nathalie Rocques
, Stéphane Romero
, Alexis Gautreau
, Florent Blanchard
, Gilles Frison
, Bastien Nay

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

Abstract

An intramolecular Diels–Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels–Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines while actin polymerization is preserved.

Original language	English
Pages (from-to)	16686-16691
Number of pages	6
Journal	Chemistry - A European Journal
Volume	24
Issue number	62
DOIs	https://doi.org/10.1002/chem.201804023
Publication status	Published - 7 Nov 2018

Keywords

antitumor agents
density functional calculations
medium-ring compounds
natural products
organocatalysis

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/chem.201804023

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Zaghouani, M., Gayraud, O., Jactel, V., Prévost, S., Dezaire, A., Sabbah, M., Escargueil, A., Lai, T. L., Le Clainche, C., Rocques, N., Romero, S., Gautreau, A., Blanchard, F., Frison, G., & Nay, B. (2018). Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties. Chemistry - A European Journal, 24(62), 16686-16691. https://doi.org/10.1002/chem.201804023

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title = "Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties",

abstract = "An intramolecular Diels–Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels–Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines while actin polymerization is preserved.",

keywords = "antitumor agents, density functional calculations, medium-ring compounds, natural products, organocatalysis",

author = "Mehdi Zaghouani and Oscar Gayraud and Vincent Jactel and S{\'e}bastien Pr{\'e}vost and Ambre Dezaire and Mich{\`e}le Sabbah and Alexandre Escargueil and Lai, \{Thanh Lan\} and \{Le Clainche\}, Christophe and Nathalie Rocques and St{\'e}phane Romero and Alexis Gautreau and Florent Blanchard and Gilles Frison and Bastien Nay",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = nov,

day = "7",

doi = "10.1002/chem.201804023",

language = "English",

volume = "24",

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journal = "Chemistry - A European Journal",

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Zaghouani, M, Gayraud, O, Jactel, V, Prévost, S, Dezaire, A, Sabbah, M, Escargueil, A, Lai, TL, Le Clainche, C , Rocques, N , Romero, S , Gautreau, A, Blanchard, F, Frison, G & Nay, B 2018, 'Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties', Chemistry - A European Journal, vol. 24, no. 62, pp. 16686-16691. https://doi.org/10.1002/chem.201804023

TY - JOUR

T1 - Multifaceted Study on a Cytochalasin Scaffold

T2 - Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties

AU - Zaghouani, Mehdi

AU - Gayraud, Oscar

AU - Jactel, Vincent

AU - Prévost, Sébastien

AU - Dezaire, Ambre

AU - Sabbah, Michèle

AU - Escargueil, Alexandre

AU - Lai, Thanh Lan

AU - Le Clainche, Christophe

AU - Rocques, Nathalie

AU - Romero, Stéphane

AU - Gautreau, Alexis

AU - Blanchard, Florent

AU - Frison, Gilles

AU - Nay, Bastien

PY - 2018/11/7

Y1 - 2018/11/7

N2 - An intramolecular Diels–Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels–Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines while actin polymerization is preserved.

AB - An intramolecular Diels–Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels–Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines while actin polymerization is preserved.

KW - antitumor agents

KW - density functional calculations

KW - medium-ring compounds

KW - natural products

KW - organocatalysis

U2 - 10.1002/chem.201804023

DO - 10.1002/chem.201804023

M3 - Article

C2 - 30168631

AN - SCOPUS:85055347131

SN - 0947-6539

VL - 24

SP - 16686

EP - 16691

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 62

ER -

Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties

Abstract

Keywords

UN SDGs

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