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Synthesis of pyrazoline fatty chain derivatives and its effects on melanoma cells
Priscila Antiqueira-Santos1, Wystan Kreisly Othon Teixeira2, Alex Fabiani Claro Flores2
1Programa de Pós-graduação em Ciências Fisiológicas, Instituto de Ciências Biológicas, Universidade Federal do Rio Grande - FURG, Rio Grande, RS, Brazil; Laboratório de Cultura Celular, Instituto de Ciências Biológicas, Universidade Federal do Rio Grande - FURG, Rio Grande do Sul, Brazil.
Abstract:
Skin cancer is the most common type of cancer in Brazil, representing 30% of all cases. Among these, melanoma represents only 3% of malignant neoplasms; however, it is the most serious and has a high capacity for metastasis. For this reason, it is extremely important to identify more efficient compounds and treatments that stop or decrease the proliferation of melanoma, even in its more advanced stages. This work reports the synthesis and biological evaluation of two homologous series of pyrazoline fatty chain derivatives as potent antitumoral agents in the melanoma B16F10 cell line. Cells were treated with pyrazoline fatty chain compounds (3, 30, 300, and 3000 μM) for 0, 24, 48, and 72 h. Decreased cell viability was observed when using most compounds at different concentrations and times. The structure-activity relationship (SAR) between antitumoral activity and the number of carbons and lipophilicity, as well as the oxygen-sulfur bioisosteric exchange, was evaluated. Among the tested derivatives, the lipophilic compounds 5-hydroxy-5-(trifluoromethyl)-3-undecyl-4,5-dihydro-1H-pyrazole-1-carboxamide (2d) and 5-hydroxy-5-(trifluoromethyl)-3-undecyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamide (3d) showed the best results in the B16F10 cell line, as they produced the best cell viability decrease effects. The presence of fatty unbranched undecyl chain in the molecular structure appears to be important for its antimelanoma properties.
Insights
New pyrazoline fatty chain derivatives show potent antitumoral activity against melanoma cells. These compounds, particularly those with an undecyl chain, effectively decrease melanoma B16F10 cell viability, offering promising therapeutic potential.
Area of Science:
- Medicinal Chemistry
- Oncology
- Pharmacology
Background:
- Skin cancer is a prevalent malignancy in Brazil, with melanoma being the most aggressive form.
- Melanoma's high metastatic potential necessitates the development of novel therapeutic agents.
- Targeting melanoma proliferation, even in advanced stages, is crucial for effective treatment.
Purpose of the Study:
- To synthesize and evaluate pyrazoline fatty chain derivatives as potential antitumoral agents.
- To investigate the structure-activity relationship (SAR) of these compounds against melanoma.
- To identify lead compounds with significant antimelanoma activity.
Main Methods:
- Synthesis of two homologous series of pyrazoline fatty chain derivatives.
- Biological evaluation using the melanoma B16F10 cell line.
- Assessment of cell viability at various compound concentrations and time points.
- Structure-activity relationship analysis focusing on lipophilicity and chain length.
Main Results:
- Most synthesized pyrazoline derivatives demonstrated decreased melanoma cell viability.
- Compounds 2d and 3d, featuring a trifluoromethyl group and an undecyl chain, exhibited the most potent effects.
- Lipophilicity and the presence of an unbranched undecyl chain were identified as key factors for antimelanoma activity.
Conclusions:
- Pyrazoline fatty chain derivatives are effective antitumoral agents against melanoma B16F10 cells.
- Specific lipophilic derivatives, such as 2d and 3d, show significant promise for further development.
- The undecyl chain is a critical structural feature for enhancing antimelanoma efficacy.
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