Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro

Tumosienė, Ingrida; Jonuškienė, Ilona; Kantminienė, Kristina; Mickevičius, Vytautas; Petrikaitė, Vilma

doi:10.3390/ijms22157799

Cited by 30 publications

(30 citation statements)

References 86 publications

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“…Naturally occurring indole, quinoline and indoloquinoline heterocyclic cores are particularly important due to their diverse biological activities, which inspire many researchers to synthesize series of hybrid systems with different spacers [ 8 , 9 , 10 , 11 ]. Natural and synthetic isatin scaffolds have received much attention from many researchers due to their wide pharmaceutical application as antimicrobial, antioxidant, anticancer and antimalarial agents [ 12 , 13 , 14 , 15 ]. On the other hand, quinoline’s core structure represents a promising surrogate in drug design and development.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening

et al. 2022

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Isatin–quinoline conjugates 10a–f and 11a–f were assembled by the reaction of N-(bromobutyl) isatin derivatives 3a, b with aminoquinolines 6a–c and their corresponding hydrazinyl 9a–c in good yields. The structures of the resulting conjugates were established by spectroscopic tools and showed data consistent with the proposed structures. In vitro antibacterial activity against different bacterial strains was evaluated. All tested conjugates showed significant biocidal activity with lower MIC than the first line drugs chloramphenicol and ampicillin. Conjugates 10a, 10b and 10f displayed the most potent activity against all clinical isolates. The antibiofilm activity for all tested conjugates was screened against the reference drug vancomycin using the MRSA strain. The results revealed that all conjugates had an inhibitory activity against biofilm formation and conjugate. Conjugate 11a showed 83.60% inhibition at 10 mg/mL. In addition, TEM studies were used to prove the mechanism of antibacterial action of conjugates 10a and 11a against (MRSA). Modeling procedures were performed on 10a–f and 11a–f and interestingly the results were nearly consistent with the biological activities. In addition, in silico pharmacokinetic evaluation was performed and revealed that the synthesized compounds 10a–f and 11a–f were considered drug-like molecules with promising bioavailability and high GI absorption. The results confirmed that the title compounds caused the disruption of bacterial cell membranes and could be used as potential leads for the further development and optimization of antibacterial agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening

et al. 2022

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“…Compound effect on cell colony formation and growth was established by clonogenic assay, as previously published [ 45 ]. Briefly, MIA PaCa-2 and PANC-1 cells were seeded into 12-well plates (Corning) at a density of 200 cells/well in 1 mL of medium and treated with sunitinib derivatives at the concentrations representing 10% and 90% of calculated EC 50 value.…”

Section: Methodsmentioning

confidence: 99%

Anticancer Activity of Sunitinib Analogues in Human Pancreatic Cancer Cell Cultures under Normoxia and Hypoxia

Skaraitė

Maccioni

Petrikaitė

2023

IJMS

Self Cite

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Pancreatic cancer remains one of the deadliest cancer types. It is usually characterized by high resistance to chemotherapy. However, cancer-targeted drugs, such as sunitinib, recently have shown beneficial effects in pancreatic in vitro and in vivo models. Therefore, we chose to study a series of sunitinib derivatives developed by us, that were proven to be promising compounds for cancer treatment. The aim of our research was to evaluate the anticancer activity of sunitinib derivatives in human pancreatic cancer cell lines MIA PaCa-2 and PANC-1 under normoxia and hypoxia. The effect on cell viability was determined by the MTT assay. The compound effect on cell colony formation and growth was established by clonogenic assay and the activity on cell migration was estimated using a ‘wound healing’ assay. Six out of 17 tested compounds at 1 µM after 72 h of incubation reduced cell viability by 90% and were more active than sunitinib. Compounds for more detailed experiments were chosen based on their activity and selectivity towards cancer cells compared to fibroblasts. The most promising compound EMAC4001 was 24 and 35 times more active than sunitinib against MIA PaCa-2 cells, and 36 to 47 times more active against the PANC-1 cell line in normoxia and hypoxia. It also inhibited MIA PaCa-2 and PANC-1 cell colony formation. Four tested compounds inhibited MIA PaCa-2 and PANC-1 cell migration under hypoxia, but none was more active than sunitinib. In conclusion, sunitinib derivatives possess anticancer activity in human pancreatic adenocarcinoma MIA PaCa-2 and PANC-1 cell lines, and they are promising for further research.

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“…Further the important 20 amino acids have been connected to a number of substrates to achieve the potent biological activities like antibacterial (Kaminski and Feix, 2011), antifungal (Sakıyan et al, 2004), anticancer(Abd-Elhamid et al, 2021), inhibitors of Type B Monoamine Oxidase (Leonetti et al, 2007), antibrotic (Li et al, 2021). It was also observed that N-Substituted amino acids are more potent against a number of activities like PPARγ agonist activity (Peiretti et al, 2020), hyperalphalipoproteinaemic activity (Baggaley et al, 1988), anti-in ammatory activity (Sakıyan et al, 2004), anti-phlogistic activity(Abd-Elhamid et al, 2021), anti-hypertensive (Stanton et al, 1983), anti-oxidant activity (Tumosienė et al, 2021), and anti-phlogistic activity (Bruno et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis and Antimicrobial Evaluation of some N-Phenyl α-Amino Acids

Singh

Goswami

et al. 2023

Preprint

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In the present report, authors described a new synthetic route for the generation of N-phenyl amino acid derivatives using CO2 by C-C coupling reaction in an undivided cell containing a combination of Mg-Pt electrodes. The reactions were completed in a short time without the formation of any other side product. The final products were purified by a simple recrystallization procedure. The structures of newly prepared compounds were established by advanced spectroscopic techniques like 1H, 13C NMR, IR, & ESI-MS. All the prepared derivatives have shown well to excellent resistance tested bacterial and fungal strains. Interestingly, it was observed that the presence of polar groups (capable of forming H-bonds) like -OH (4d) and -NO2 (4e) at the para position of the phenyl ring show activity equivalent to the standard drugs.

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Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro

Cited by 30 publications

References 86 publications

Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening

Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening

Anticancer Activity of Sunitinib Analogues in Human Pancreatic Cancer Cell Cultures under Normoxia and Hypoxia

Electrochemical Synthesis and Antimicrobial Evaluation of some N-Phenyl α-Amino Acids

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