Structure-based design, synthesis and antitumoral evaluation of enulosides

Jonh A M Santos; Cosme S Santos; Claudia L A Almeida; Thiago D S Silva; João R Freitas Filho; Gardenia C G Militão; Teresinha G da Silva; Carlos H B da Cruz; Juliano C R Freitas; Paulo H Menezes

doi:10.1016/j.ejmech.2017.01.036

Structure-based design, synthesis and antitumoral evaluation of enulosides

Eur J Med Chem. 2017 Mar 10:128:192-201. doi: 10.1016/j.ejmech.2017.01.036. Epub 2017 Jan 24.

Affiliations

¹ Departamento de Química, Universidade Federal Rural de Pernambuco, Rua Dom Manoel de Medeiros s/n, 52171-900, Recife, PE, Brazil; Departamento de Química, Universidade Federal de Pernambuco, Av. Jornalista Anibal Fernandes s/n, 50670-901, Recife, PE, Brazil.
² Departamento de Fisiologia e Farmacologia, Universidade Federal de Pernambuco, Av. Prof. Moraes Rego, 1235, 50670-901, Recife, PE, Brazil.
³ Departamento de Química, Universidade Federal Rural de Pernambuco, Rua Dom Manoel de Medeiros s/n, 52171-900, Recife, PE, Brazil.
⁴ Departamento de Antibióticos, Universidade Federal de Pernambuco, Av. Prof. Moraes Rego, 1235, 50670-901, Recife, PE, Brazil.
⁵ Departamento de Química, Universidade Federal de Pernambuco, Av. Jornalista Anibal Fernandes s/n, 50670-901, Recife, PE, Brazil.
⁶ Departamento de Química, Universidade Federal Rural de Pernambuco, Rua Dom Manoel de Medeiros s/n, 52171-900, Recife, PE, Brazil; Centro de Educação e Saúde, Universidade Federal de Campina Grande, Acesso Professora Maria Anita Furtado Coelho, s/n, 58175-000, Cuité, PB, Brazil. Electronic address: julianocrufino@yahoo.com.br.
⁷ Departamento de Química, Universidade Federal de Pernambuco, Av. Jornalista Anibal Fernandes s/n, 50670-901, Recife, PE, Brazil. Electronic address: paulo.menezes@pq.cnpq.br.

PMID: 28189083
DOI: 10.1016/j.ejmech.2017.01.036

Abstract

Enulosides, carbohydrate derivatives containing an α,β-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60 cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. 2016 Elsevier Ltd. All rights reserved.

Keywords: Antitumoral; CRM-1; Enulosides; Pseudoglycosides.

Publication types

Evaluation Study

MeSH terms

Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology*
Biological Products / chemistry
Biological Products / pharmacology*
Carbohydrates / chemistry*
Cell Proliferation / drug effects*
Drug Design*
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Neoplasms / drug therapy
Neoplasms / pathology
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

Antineoplastic Agents
Biological Products
Carbohydrates