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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.)

Methoxychalcones: Effect of Methoxyl Group on the Antifungal Antibacterial and Antiproliferative Activities

Full text
Author(s):
Marques, Beatriz C. [1] ; Santos, Mariana B. [1] ; Anselmo, Daiane B. [1] ; Monteiro, Diego A. [2] ; Gomes, Eleni [2] ; Saiki, Marilia F. C. [2] ; Rahal, Paula [2] ; Rosalen, Pedro L. [3] ; Sardi, Janaina C. O. [3] ; Regasini, Luis O. [1]
Total Authors: 10
Affiliation:
[1] Sao Paulo State Univ Unesp, Inst Biosci Humanities & Exact Sci, Dept Chem & Environm Sci, BR-15054000 Sao Jose Do Rio Preto, SP - Brazil
[2] Sao Paulo State Univ Unesp, Inst Biosci Humanities & Exact Sci, Dept Biol, BR-15054000 Sao Jose Do Rio Preto, SP - Brazil
[3] Univ Campinas Unicamp, Piracicaba Dent Sch, Dept Physiol Sci, BR-13083970 Piracicaba, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Medicinal Chemistry; v. 16, n. 7, p. 881-891, 2020.
Web of Science Citations: 0
Abstract

Background: Chalcones substituted by methoxyl groups have presented a broad spectrum of bioactivities, including antifungal, antibacterial and antiproliferative effects. However, a clear and unambiguous investigation about the relevance of this substituent on the chalcone framework has not been described. Objective: The purpose of this work is to assess the antibacterial, antifungal and antiproliferative activities of the two series of seventeen synthesized regioisomeric methoxychalcones. Series I and II were constituted by cbalcones substituted by methoxyl groups on rings A (5-12) and B (13-21), respectively. In addition, the library of methoxychalcones was submitted to in silico drug-likeness and pharmacokinetics properties predictions. Methods: Methoxychalcones were synthesized and their structures were confirmed by NMR spectral data analyses. Evaluations of antimicrobial activity were performed against five species of Candida, two Gram-negative and five Gram-positive species. For antiproliferative activity, methoxychalcones were evaluated against four human tumorigenic cell lines, as well as human non-tumorigenic keratinocytes. Drug-likeness and pharmacokinetics properties were predicted using Molinspiration and PreADMET toolkits. Results: In general, chalcones of series I are the most potent antifungal, antibacterial and antiproliferative agents. 3', 4', 5'-Trimethoxychalcone (12) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 mu g/mL), eight times more potent than fluconazole (reference antifungal drug). 3'-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 mu g/mL). 2',5'-Dimethoxychalcone (9) displayed potent antiproliferative effect against C-33A (cervix), A-431 (skin) and MCF-7 (breast), with IC50 values ranging from 7.7 to 9.2 mu M. Its potency was superior to curcumin (reference antiproliferative compound), which exhibited IC50 values ranging from 10.4 to 19.0 mu M. Conclusion: Our studies corroborated the relevance of methoxychalcones as antifungal, antibacterial and antiproliferative agents. In addition, we elucidated influence of the position and number of methoxyl groups toward bioactivity. In silico predictions indicated good drug-likeness and pharmacokinetics properties to the library of methoxychalcones. (AU)

FAPESP's process: 14/18330-0 - Synthesis and biological evaluation of curcumin-cinnamaldehyde hybrids as bacterial cell division inhibitors
Grantee:Luis Octávio Regasini
Support type: Regular Research Grants
FAPESP's process: 17/09245-7 - Investigation of Chalcones against Staphylococcus aureus MSSA and MRSA: evaluation of Antibacterial, Antibiofilm, Anti-adsion Activity and Toxicity on Galleria mellonella
Grantee:Beatriz de Carvalho Marques
Support type: Scholarships in Brazil - Master
FAPESP's process: 14/18577-5 - Preparation and Biological Evaluation of Curcumin-Cinnamaldehyde Hybrids as Bacterial Cell Division Inhibitors: Methoxychalcones
Grantee:Beatriz de Carvalho Marques
Support type: Scholarships in Brazil - Scientific Initiation
FAPESP's process: 09/53989-4 - Acquisition of a nuclear magnetic resonance spectrometer for studies of biomolecules
Grantee:Raghuvir Krishnaswamy Arni
Support type: Multi-user Equipment Program
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 type: Regular Research Grants
FAPESP's process: 16/08084-7 - Preparation and Biological Evaluation of Curcumin-Cinnamaldehyde Hybrids as Bacterial Cell Division Inhibitors: Methoxychalcones (Part 2)
Grantee:Beatriz de Carvalho Marques
Support type: Scholarships in Brazil - Scientific Initiation
FAPESP's process: 14/50926-0 - INCT 2014: biodiversity and natural products
Grantee:Vanderlan da Silva Bolzani
Support type: BIOTA-FAPESP Program - Thematic Grants