In vitro cytotoxicity and structure-activity relationship approaches of ent-kaurenoic acid derivatives against human breast carcinoma cell line

Costa, Rafaela Lira Mendes; Bastos, Jairo Kenupp; Costa, Maria Laura; Ferreira, Márcia M. C.; Mizuno, Cássia S.; Caramori, Giovanni F.; Nagurniak, Glaucio Régis; Simão, Marília R.; Santos, Raquel; Veneziani, Rodrigo Cássio Sola; Ambrósio, Sérgio Ricardo; Parreira, Renato L.T.

doi:10.1016/j.phytochem.2018.10.005

Cited by 22 publications

(21 citation statements)

References 49 publications

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“…The MIC, MBC, and MICB 50 values displayed by compounds 8 and 9 ( Table 1; Figure 2) denote that these natural compounds are much less efficient against MRDB than the results displayed by VAN (positive control). However, it is crucial to observe that during the development of drugs based on natural products, discovering novel biologically promising chemical entities is the first step [37] . These natural compounds represent molecular frameworks to be optimized through semi‐synthetic strategies, to access a new series of natural product analogs, and finally obtain derivatives more effective and less toxic [37,38] .…”

Section: Resultsmentioning

confidence: 99%

“…However, it is crucial to observe that during the development of drugs based on natural products, discovering novel biologically promising chemical entities is the first step [37] . These natural compounds represent molecular frameworks to be optimized through semi‐synthetic strategies, to access a new series of natural product analogs, and finally obtain derivatives more effective and less toxic [37,38] . In this sense, the results described here point out compounds 8 and 9 as starting points from BRP to develop new medicines against MRDB through medicinal chemistry approaches.…”

Section: Resultsmentioning

confidence: 99%

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Green and Red Brazilian Propolis: Antimicrobial Potential and Anti‐Virulence against ATCC and Clinically Isolated Multidrug‐Resistant Bacteria

Silva

Braun

et al. 2021

Chemistry & Biodiversity

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Brazilian green and red propolis stand out as commercial products for different medical applications. In this article, we report the antimicrobial activities of the hydroalcoholic extracts of green (EGP) and red (ERP) propolis, as well as guttiferone E plus xanthochymol (8) and oblongifolin B (9) from red propolis, against multidrug‐resistant bacteria (MDRB). We undertook the minimal inhibitory (MIC) and bactericidal (MBC) concentrations, inhibition of biofilm formation (MICB50), catalase, coagulase, DNase, lipase, and hemolysin assays, along with molecular docking simulations. ERP was more effective by displaying MIC and MBC values <100 μg mL−1. Compounds 8 and 9 displayed the lowest MIC values (0.98 to 31.25 μg mL−1) against all tested Gram‐positive MDRB. They also inhibited the biofilm formation of S. aureus (ATCC 43300 and clinical isolate) and S. epidermidis (ATCC 14990 and clinical isolate), with MICB50 values between 1.56 and 6.25 μg mL−1. The molecular docking results indicated that 8 and 9 might interact with the catalase's amino acids. Compounds 8 and 9 have great antimicrobial potential.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Green and Red Brazilian Propolis: Antimicrobial Potential and Anti‐Virulence against ATCC and Clinically Isolated Multidrug‐Resistant Bacteria

Silva

Braun

et al. 2021

Chemistry & Biodiversity

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“…Recently, the frontier orbitals, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and their energy gaps have been used to prove numerous chemical reactivity forms of the biological characters. Moreover, several biological activities such as antifungal (Joshi et al, 2018 , 2020 ), anticancer (Kumar et al, 2018 ; Hagar et al, 2019 ; Khodair et al, 2020 ), antimicrobial (Grover et al, 2000 ; Malhotra et al, 2017 ; Kumer et al, 2019 ), cytotoxic (Aljuhani et al, 2018 ; Da Costa et al, 2018 ; Rachedi et al, 2019 ) activities and a new-drug-design field (Lewis, 2003 ) could be investigated in terms of the relationship with the energy of the FMOs.…”

Section: Resultsmentioning

confidence: 99%

Novel 2-Hydroselenonicotinonitriles and Selenopheno[2, 3-b]pyridines: Efficient Synthesis, Molecular Docking-DFT Modeling, and Antimicrobial Assessment

et al. 2021

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Selenium containing heterocyclic compounds gained great interest as bioactive molecules as of late. This report explores the design, synthesis, characterization, and antimicrobial screening of new pyridine derivatives endowed with selenium moieties. A one-pot multicomponent system with a solvent-free, microwave irradiation environment was employed to afford this series. The spectroscopic techniques were exploited to verify the structures of the synthesized derivatives. Additionally, the agar diffusion method was employed to determine the antimicrobial activity of all the desired compounds. Of all the synthesized molecules, 9b, 12b, 14f, and 16d exhibited well to remarkable antibacterial and antifungal activities. Moreover, derivative 14f demonstrated the most potent antibacterial and antifungal performance. The results were also supported by molecular docking studies, utilizing the MOE (molecular operating environment) which revealed the best binding mode with the highest energy interaction within the binding pocket. Lastly, theoretical DFT calculations were carried out in a gas phase at B3LYP 6-311G (d,p) basis set to predict the molecular geometries and chemical reactivity descriptors. DFT results have been used to illustrate that molecular docking findings and biological activity assessments.

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“…[10] Among the molecular characteristics to be used for structure-pharmacological activity relationship, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies have been shown to correlate particularly well with various biological activities. [36][37][38][39][40][41][42] It is to be taken into account that biological activity or generation of the stable "rigid" structure with the receptors depends on the chemical constitution of target, including its possible electron structure.…”

Section: Introductionmentioning

confidence: 99%

“…Among the molecular characteristics to be used for structure‐pharmacological activity relationship, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies have been shown to correlate particularly well with various biological activities …”

Section: Introductionmentioning

confidence: 99%

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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A series of new 1,3‐oxazole derivatives, containing in position 5 both donor and acceptor substituents were synthesized. These substances were considered as potentially active anticancer pharmacophores in the human tumor cell line panel derived from nine cancer types, including lung, colon, melanoma, renal, ovarian, brain, leukemia, breast, and prostate. Primary in vitro one‐dose anticancer screening was shown that compounds with acceptor substituents (such as –C(O)OMe, –CN) in the position 5 inhibit the growth of most cell lines, and compounds with donor substituents (such as –NHR, −SR) in the position 5 do not practically inhibit the growth of cancer cell lines. It can be assumed that the pharmacological activity of 1,3‐oxazole derivatives depends on donor/acceptor nature of the substituents in position 5. It was proposed to evaluate the donor/acceptor ability of 1,3‐oxazole derivatives using the special parameter φ0, which takes into account the relative position of the boundary levels (HOMO end LUMO). The quantum‐chemical modeling was performed; the special parameter φ0 for 1,3‐oxazole derivatives correlates with the experimental results. Quantum‐chemical calculations of the special parameter φ0 allow modeling the pharmacological activity of 1,3‐oxazole derivatives by introducing donor or acceptor substituents at position 2 or 5. This work may be useful for chemists to develop a target synthesis of potential biologically active compounds.

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In vitro cytotoxicity and structure-activity relationship approaches of ent-kaurenoic acid derivatives against human breast carcinoma cell line

Cited by 22 publications

References 49 publications

Green and Red Brazilian Propolis: Antimicrobial Potential and Anti‐Virulence against ATCC and Clinically Isolated Multidrug‐Resistant Bacteria

Green and Red Brazilian Propolis: Antimicrobial Potential and Anti‐Virulence against ATCC and Clinically Isolated Multidrug‐Resistant Bacteria

Novel 2-Hydroselenonicotinonitriles and Selenopheno[2, 3-b]pyridines: Efficient Synthesis, Molecular Docking-DFT Modeling, and Antimicrobial Assessment

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

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