Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models

Žukauskas, Mindaugas; Grybaitė, Birutė; Jonutė, Paulina; Vaickelionienė, Rita; Gibieža, Paulius; Vaickelionis, Giedrius; Dragūnaitė, Bertina; Anusevičius, Kazimieras; Mickevičius, Vytautas; Petrikaitė, Vilma

doi:10.1016/j.bioorg.2021.105214

Cited by 5 publications

(4 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was found that the halogen‐substituted compounds possessed better activity than unsubstituted and hydroxy‐substituted compounds, probably due to increasing the lipophilicity of the molecule, which helps in easy penetration of the drug through the lipid membranes and therefore enhances the intercellular drug delivery. [ 54–56 ] In our case, a comparison of compounds 4 and 5 , differing only in halogen atoms, showed that compound 4 with 4‐Cl substitution has higher cytotoxic activity compared with compound 5 with 4‐Br substitution. When we compare compounds 4 and 5 with compound 2 , it is clearly observed that compound 2 with 4‐OH substitution exerted a lower inhibition activity against all tested cells than compounds 4 and 5 .…”

Section: Resultsmentioning

confidence: 59%

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Mostafa

2022

J of Physical Organic Chem

View full text Add to dashboard Cite

An operationally efficient and affordable lactone-to-lactam transformation was designed from pyrano [3,2-c]quinolinone 1 to obtain 4-hydroxybenzo [h][1,6] naphthyridine-2,5-dione 2 utilizing ammonium acetate. The newly synthesized compound 2 was subjected to different electrophilic substitution reactions such as nitration, chlorination, bromination, and N-acylation to obtain novel benzo [h][1,6]naphthyridine derivatives with different substituents at C-3, C-4, and NH. Structures of novel products were achieved by elemental analyses and spectroscopic techniques. The benzonapthyridine derivatives were screened for their antitumor activities against some cancer cell lines including HepG-2, HCT-116, and MCF-7. All the examined compounds revealed strong, good, moderate to weak anticancer activity compared with 5-fluorouracil as a reference standard. Compound (3, -3NO 2 ) was the most cytotoxic one and exhibited a higher inhibitory activity than the standard drug against HCT-116 and MCF-7 with IC 50 values of 20.7 ± 1.9 and 22.5 ± 2.1 μg/ml, respectively, and strong activity against HepG-2 with IC 50 = 15.3 ± 0.7 μg/ml. Moreover, a molecular docking study was carried out for the tested compounds against the crystallographic structure of the Topo II enzyme as a potential target to investigate their binding modes. Docking results showed that compound 6b fitted well into the active site of topoisomerase II (PDB ID: 1ZXM) with hydrogen bond interactions.

show abstract

Section: Resultsmentioning

confidence: 59%

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Mostafa

2022

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

“…[43] Previously, we have synthesized a library of N,N-disubstituted β-aminoacids derivatives containing hydrazone and azole fragments and have evaluated their biological properties, which appeared to possess the convincing anticancer effect against triple-negative breast cancer and glioblastoma cells in vitro. [44] They demonstrated promising antimicrobial, [45][46][47][48] significant antibacterial, [49][50][51][52] and in addition, antiviral and antioxidant [51,52] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Assays of Novel N,N¹‐Disubstituted 2,2′‐Dithiodianiline Derivatives

et al. 2023

Self Cite

View full text Add to dashboard Cite

A series of novel 1,2‐bissubstituted disulfanes bearing beta‐amino acid, dihydropyrimidine‐2,4‐(1H,3H)‐dione, hydrazide, hydrazone and azole moieties were synthesized. The antibacterial activity was evaluated by determining minimum inhibition (by broth microdilution) and minimum bactericidal (by growth on agar) concentrations. The assessment revealed that MIC values for L. monocytogenes varied between 3.9 and 62.5 μg/mL as well as for S. aureus ranged between 7.8 and 250 μg/mL, with the exception of one compound with much weaker MIC of 500 μg/mL. The MBC values for L. monocytogenes have been found to be of 7.8–250 μg/mL, while S. aureus demonstrated the higher resistance and MBCs varied in the range of 7.8–500 μg/mL. The determined MBC/MIC ratios showed that eleven compounds were classified bactericidal agents for all tested bacteria.

show abstract

“…Previously, we have synthesized a library of N,N-disubstituted β-aminoacids derivatives containing hydrazone and azole fragments and have evaluated their biological properties, which appeared to possess the convincing anticancer effect against triple-negative breast cancer and glioblastoma cells in vitro [35], demonstrated promising antimicrobial effect [36−39], as well as signi cant antibacterial [40−43], and in addition, antiviral and antioxidant [42,43] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antibacterial assays of new N,N 1 -disubstituted 2,2’- dithiodianiline derivatives

Skrickus

Šiugždaitė

Lelešius

et al. 2022

Preprint

Self Cite

View full text Add to dashboard Cite

A series of novel 1,2-bissubstituted disulfanes bearing beta-amino acid, dihydropyrimidine-2,4-(1H,3H)-dione, hydrazide, hydrazone and azole moieties were synthesized. These disulphides were characterised by spectral and microanalysis data. On the antibacterial evaluation, they were found to have interesting antibacterial properties over a panel of the tested Gram-positive and Gram-negative bacteria: Staphylococcus aureus subs. aureus (ATCC 9144) and zoonotic agent Listeria monocytogenes (ATCC 35152), as well as Gram-negative ones, Escherichia coli (ATCC 13076) and zoonotic agent Salmonella enterica subs. enterica serovar Enteritidis (ATCC 8739). The antibacterial activity was evaluated by determining minimum inhibition (by broth microdilution) and minimum bactericidal (by growth on agar) concentrations. The assessment revealed that MIC values for L. monocytogenes varied between 3.9 and 62.5 µg/mL as well as for S. aureus ranged between 7.8 and 250 µg/mL, with the exception of one compound with much weaker MIC of 500 µg/mL. The MBC values for L. monocytogenes have been found to be of 7.8−250 µg/mL, while S. aureus demonstrated the higher resistance and MBCs varied in the range of 7.8\(\)500 µg/mL. The determined MBC/MIC ratios showed that eleven compounds were classified bactericidal agents for all tested bacteria.

show abstract

Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models

Cited by 5 publications

References 53 publications

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Synthesis, Characterization and Antibacterial Assays of Novel N,N¹‐Disubstituted 2,2′‐Dithiodianiline Derivatives

Synthesis, characterization and antibacterial assays of new N,N 1 -disubstituted 2,2’- dithiodianiline derivatives

Contact Info

Product

Resources

About

Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models

Cited by 5 publications

References 53 publications

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Synthesis, Characterization and Antibacterial Assays of Novel N,N1‐Disubstituted 2,2′‐Dithiodianiline Derivatives

Synthesis, characterization and antibacterial assays of new N,N 1 -disubstituted 2,2’- dithiodianiline derivatives

Contact Info

Product

Resources

About

Synthesis, Characterization and Antibacterial Assays of Novel N,N¹‐Disubstituted 2,2′‐Dithiodianiline Derivatives