2. Academic Validation
  3. Synthesis of novel 4-Boc-piperidone chalcones and evaluation of their cytotoxic activity against highly-metastatic cancer cells

Synthesis of novel 4-Boc-piperidone chalcones and evaluation of their cytotoxic activity against highly-metastatic cancer cells

  • Bioorg Med Chem Lett. 2020 Jan 1;30(1):126760. doi: 10.1016/j.bmcl.2019.126760.
Carlimar Ocasio-Malavé 1,  Metsiel J Donate 2,  María M Sánchez 3,  Jesús M Sosa-Rivera 2,  Joseph W Mooney 1,  Tomás A Pereles-De León 1,  Néstor M Carballeira 4,  Beatriz Zayas 5,  Christian E Vélez-Gerena 5,  Magaly Martínez-Ferrer 2,  David J Sanabria-Ríos 6
Affiliations

Affiliations

  • 1 Faculty of Science and Technology, Department of Natural Sciences, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, USA.
  • 2 School of Pharmacy, Department of Pharmaceutical Sciences, University of Puerto Rico, Medical Sciences Campus, PO Box 365067, San Juan, PR 00936, USA; University of Puerto Rico Comprehensive Cancer Center, PO Box 363027, San Juan, PR 00936, USA.
  • 3 University of Puerto Rico Comprehensive Cancer Center, PO Box 363027, San Juan, PR 00936, USA.
  • 4 Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, 17 Ave Universidad STE 1701, San Juan, PR 00925, USA.
  • 5 School of Science, Technology & Environment, Universidad Ana G. Méndez, Cupey Campus, PO Box 21150, San Juan, PR 00928, USA.
  • 6 Faculty of Science and Technology, Department of Natural Sciences, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, USA. Electronic address: dsanabria@intermetro.edu.
PMID: 31767266 DOI: 10.1016/j.bmcl.2019.126760
Abstract

In this study, six curcuminoids containing a tert-butoxycarbonyl (Boc) piperidone core were successfully synthesized, five of them are novel compounds reported here for the first time. These compounds were prepared through an aldolic condensation by adding tetrahydropyranyl-protected benzaldehydes or substituted benzaldehyde to a reaction mixture containing 4-Boc-piperidone and lithium hydroxide in an alcoholic solvent. A 44-94% yield was obtained supporting the developed methodology as a good strategy for the synthesis of 4-Boc-piperidone Chalcones. Cytotoxic activity against LoVo and COLO 205 human colorectal cell lines was observed at GI50 values that range from 0.84 to 34.7 μg/mL, while in PC3 and 22RV1 human prostate Cancer cell lines, GI50 values ranging from 17.1 to 22.9 μg/mL were obtained. Results from biochemical assays suggest that the cytotoxicity of the 4-Boc-piperidone Chalcones can be linked to their ability to induce Apoptosis, decrease the activity of NFκB and cellular proliferation. Our findings strongly support the potential of Boc-piperidone Chalcones as novel cytotoxic agents against highly-metastatic Cancer cells.

Keywords

Apoptosis; Cancer; Cell proliferation; Curcumin; Curcumin analogs; Cytotoxic agents.

Figures
嗨！很高兴为您提供帮助！

尊敬的 MCE 客户您好，
请您选择所在区域，我们将转接对应客服为您服务！

热门区域

A

B

C

F

G

H

J

L

N

Q

S

T

X

Y

Z

热 A B C F G H J L N Q S T X Y Z