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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Curcumin-cinnamaldehyde hybrids as antiproliferative agents against women's cancer cells

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Author(s):
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Anselmo, Daiane B. [1] ; Polaquini, Carlos R. [1] ; Marques, Beatriz C. [1] ; Ayusso, Gabriela M. [1] ; Assis, Leticia R. [1] ; Torrezan, Guilherme S. [1] ; Rahal, Paula [2] ; Fachin, Ana L. [3] ; Calmon, Marilia F. [2] ; Marins, Mozart A. [3] ; Regasini, Luis O. [1]
Total Authors: 11
Affiliation:
[1] Sao Paulo State Univ Unesp, Inst Biosci Humanities & Exact Sci, Dept Chem & Environm Sci, Lab Antibiot & Chemotherapeut, BR-15054000 Sao Jose Do Rio Preto, SP - Brazil
[2] Sao Paulo State Univ Unesp, Inst Biosci Humanities & Exact Sci, Dept Biol, Lab Genom Studies, BR-15054000 Sao Jose Do Rio Preto, SP - Brazil
[3] Univ Ribeirao Preto Unaerp, Biotechnol Unit, Lab Mol Genet & Bioinformat, BR-14096900 Ribeirao Preto, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: MEDICINAL CHEMISTRY RESEARCH; v. 30, n. 11 AUG 2021.
Web of Science Citations: 0
Abstract

Curcumin and cinnamaldehyde are natural products whose antineoplastic activity has been well explored in biological evaluations. However, their poor chemical stability under physiological conditions has been an obstacle to their use as therapeutic agents. Herein, we designed and synthesized two series of curcumin-cinnamaldehyde hybrids by removing reactive functionalities, including beta-diketone and aldoxyl moieties. All compounds were evaluated by the MTT assay to determine their antiproliferative activity against women's cancer cells. Compound 5a (3 `-hydroxychalcone) demonstrated potent antiproliferative activity against all cancer cell lines tested, with IC50 values ranging from 2.7 to 36.5 mu M. Compound 5a was more active and selective than curcumin and cinnamaldehyde (parent compounds) against the CaSki, SiHa, C33, and A431 cell lines, displaying a higher selectivity index (SI = 8.5) than curcumin (SI = 0.8) toward the non-tumorigenic HaCaT cell line. Clonogenic experiments indicated that compound 5a inhibited A431 colony formation in a concentration-dependent manner. In addition, 5a was more stable than its parent compounds in pH 7.4 at 37 degrees C. In silico investigations suggested that 5a has good drug-likeness properties. In conclusion, our results indicate the use of curcumin and cinnamaldehyde as parent compounds for the design of hybrids with attractive antiproliferative activity and chemical stability. (AU)

FAPESP's process: 18/15083-2 - Synthesis and biological evaluation of isobavachalcone (IBC) and analogs as potential agents against tuberculosis
Grantee:Luis Octávio Regasini
Support Opportunities: Regular Research Grants
FAPESP's process: 14/50880-0 - INCT 2014: comparative and functional genomics and citrus-assisted breeding
Grantee:Marcos Antonio Machado
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 14/18330-0 - Synthesis and biological evaluation of curcumin-cinnamaldehyde hybrids as bacterial cell division inhibitors
Grantee:Luis Octávio Regasini
Support Opportunities: Regular Research Grants
FAPESP's process: 09/53989-4 - Acquisition of a nuclear magnetic resonance spectrometer for studies of biomolecules
Grantee:Raghuvir Krishnaswamy Arni
Support Opportunities: Multi-user Equipment Program
FAPESP's process: 14/50926-0 - INCT 2014: biodiversity and natural products
Grantee:Vanderlan da Silva Bolzani
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants