Synthesis, characterization, in silico approach and in vitro antiproliferative activity of RPF151, a benzodioxole sulfonamide analogue designed from capsaicin scaffold

Author(s):Show less -

Tavares, Mauricio T. ^[1] ; Pasqualoto, Kerly F. M. ^[2] ; van de Streek, Jacco ^[3] ; Ferreira, Adilson K. ^[4] ; Azevedo, Ricardo A. ^[4] ; Damiao, Mariana C. F. C. B. ^[1] ; Rodrigues, Cecilia P. ^[5] ; de-Sa-Junior, Paulo L. ^[6] ; Barbuto, Jose A. M. ^{[4, 7]} ; Parise-Filho, Roberto ^[1] ; Ferreira, Fabio F. ^[8]

Affiliation

^[1] Univ Sao Paulo, Fac Pharmaceut Sci, Dept Pharm, BR-5508000 Sao Paulo, SP - Brazil

^[2] Butantan Inst, Biochem & Biophys Lab, BR-05503900 Sao Paulo, SP - Brazil

^[3] Univ Copenhagen, Dept Pharm, DK-2100 Copenhagen - Denmark

^[4] Univ Sao Paulo, Dept Immunol, Inst Biomed Sci, Lab Tumor Immunol, BR-05508900 Sao Paulo, SP - Brazil

^[5] Fed Univ Para, Fac Fis, BR-68501970 Maraba, PA - Brazil

^[6] Butantan Inst, Genet Lab, BR-05503900 Sao Paulo, SP - Brazil

^[7] Univ Sao Paulo, Fac Med, Cell & Mol Therapy Ctr NUCEL NETCEM, BR-05360120 Sao Paulo, SP - Brazil

^[8] Fed Univ ABC UFABC, Ctr Nat & Human Sci CCNH, BR-09210580 Santo Andre, SP - Brazil

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1088, p. 138-146, MAY 15 2015.
• Web of Science Citations: 8

Abstract

RPF151, an alkylsulfonamide capsaicin analogue, was synthesized by a simple and efficient one-step methodology. The compound was characterized by H-1 and C-13 NMR, elemental analysis, IR and melting point. The crystal structure of RPF151 was determined by X-ray powder diffraction and its experimental arrangement was compared to the lowest-energy conformer from molecular dynamics simulation. The computational and experimental findings regarding the RPF151 structural arrangement have corroborated with one another. The compound was also tested in vitro against human umbilical vein endothelial cells (HUVEC) in order to verify its antiproliferative activity. RPF151 has significantly reduced the growth of HUVEC cells at 10 mu M, suggesting that it probably would act on the angiogenesis process. RPF151 can be considered, then, as a promising anticancer lead for designing novel antitumor agents as potential drug candidates. (C) 2015 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 13/18160-4 - Novel anticancer candidates: design, synthesis, antitumoral activity and mode of action of novel capsaicinoids and capsinoids analogues
• Grantee: Roberto Parise Filho
• Support Opportunities: Regular Research Grants
• FAPESP's process: 08/10537-3 - Study of crystalline pharmaceuticals polymorphs by X-ray powder diffraction and the Rietveld method
• Grantee: Fabio Furlan Ferreira
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 12/23233-8 - Novel anticancer candidates: synthesis and antitumoral activity of capsaicin-like sulfonate and sulfonamide analogues
• Grantee: Maurício Temotheo Tavares
• Support Opportunities: Scholarships in Brazil - Master