Cytotoxicity, anticancer, and antioxidant properties of mono and bis-naphthalimido β-lactam conjugates

Borazjani, Nassim; Behzadi, Maryam; Aseman, Marzieh Dadkhah; Jarrahpour, Aliasghar; Rad, Javad Ameri; Kianpour, Sedigheh; Iraji, Aida; Nabavizadeh, S. Masoud; Ghanbari, Mohammad; Batta, Gyula; Turos, Edward

doi:10.1007/s00044-020-02552-1

Cited by 10 publications

(3 citation statements)

References 58 publications

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“…Among the tested cell lines, compound 78 showed potent activity against TC-1 cell lines with IC 50 value 85.34 µM. Gemcitabine was used as a reference drug with IC 50 values 191.57, 153.25, and 215.01 µM, respectively [ 201 ]. Nagaraju Payili et al (2018) synthesized and evaluated anticancer activity of beta-lactam based derivatives.…”

Section: Current Advances In Nitrogen Containing Heterocycles As Anti...mentioning

confidence: 99%

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

et al. 2023

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Cancer is one of the major healthcare challenges across the globe. Several anticancer drugs are available on the market but they either lack specificity or have poor safety, severe side effects, and suffer from resistance. So, there is a dire need to develop safer and target-specific anticancer drugs. More than 85% of all physiologically active pharmaceuticals are heterocycles or contain at least one heteroatom. Nitrogen heterocycles constituting the most common heterocyclic framework. In this study, we have compiled the FDA approved heterocyclic drugs with nitrogen atoms and their pharmacological properties. Moreover, we have reported nitrogen containing heterocycles, including pyrimidine, quinolone, carbazole, pyridine, imidazole, benzimidazole, triazole, β-lactam, indole, pyrazole, quinazoline, quinoxaline, isatin, pyrrolo-benzodiazepines, and pyrido[2,3-d]pyrimidines, which are used in the treatment of different types of cancer, concurrently covering the biochemical mechanisms of action and cellular targets.

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Section: Current Advances In Nitrogen Containing Heterocycles As Anti...mentioning

confidence: 99%

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

et al. 2023

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“…For example, Ezetimibe (Zetia) is a prescribed lipid‐lowering drug that selectively reduces the intestinal absorption of cholesterol [10] . They have also been reported to exhibit potent pharmacological activates such as anticancer, [11] antifungal, [9c,11c] antioxidant, [11a,b,d] anti‐inflammation, [9a,12] anti‐HIV, [13] antidepressant, [14] antitubercular, [15] antiurease, [16] antimalaria, [17] acetylcholinesterase inhibitor, [18] carbonic anhydrase inhibitor, [18b,19] K562 human leukemia cell line inhibitor, [11d] and NAAA inhibitor [20] . Moreover, they consist of a building block to synthesize different pharmacologically active compounds [5a,21] .…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking and Antibacterial Assessment of Monocyclic β‐Lactams against Broad‐Spectrum and Nosocomial Multidrug‐Resistant Pathogens

et al. 2022

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β‐Lactam antibiotics are critical antibacterial agents and have rapidly become active ingredients in modern medicine. On the other hand, in the face of increasing rate of antibacterial resistance, there are many concerns requiring the design and synthesis of new antibacterial agents. Herein, we synthesized some monocyclic β‐lactams with various substituents through the Staudinger cycloaddition reaction. The formation of cycloadducts was confirmed by elemental analysis and different spectral data, including NMR, FTIR, and Mass spectroscopy. The investigation of in vitro antibacterial activity of synthesized β‐lactams was performed against some broad‐spectrum strains, including Escherichia coli (E. coli), streptococcus aureus (S. aureus), Salmonella Typhi (S. Typhi), Enterococcus faecalis (E. faecalis), and Candida albicans (C. albicans) and also some nosocomial multidrug‐resistant pathogens such as methicillin‐resistant Staphylococcus aureus (MRSA), and vancomycin‐resistant enterococci (VRE). Penicillin Binding Proteins (PBPs) are responsible for the cell wall synthesis process as an enzymatic target for β‐lactam antibiotics. The molecular docking study exhibited a good correlation between the calculated binding affinity to PBP and the experimental data. Based on the obtained results, compound 4 d was successfully fitted in the BPB active site, and could potentially serve as a promising lead compound for the treatment of infectious diseases.

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“…[46] Some β-lactam derivatives bearing a piperazine moiety (Scheme 1) have displayed promising antimicrobial (I, II), [47,48] antitumor (III), [49] antiurease and antioxidant (IV) [50] activities as well as tryptase inhibition (V-VIII). [51][52][53][54] Here, as a part of our ongoing efforts devoted to the design of bioactive heterocycles, [40,41,[55][56][57][58] we decided to use molecular hybridization approach as a tool to synthesize the unique combination of different classes of biologically active moieties namely β-lactam, piperazine, and sulfonamide. In this study we synthesized conjugated sulfonamide-β-lactam analogues possessing a pendant piperazine moiety, and evaluated their antiinflammatory activities by the cell-based assay, cytotoxicity, and antibacterial activities.…”

Section: Introductionmentioning

confidence: 99%

Sulfonamide‐β‐lactam Hybrids Incorporating the Piperazine Moiety as Potential Antiinflammatory Agent with Promising Antibacterial Activity

et al. 2021

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Several monocyclic β-lactams have been synthesized via a [2 + 2] ketene-imine cycloaddition reaction (Staudinger reaction) and evaluated for their biological activities. The structure of synthesized products was confirmed by spectral data and elemental analyses. β-Lactams 4 b and 4 h exhibited 31 and 27 anti-inflammatory ratios, respectively, which are as well as the well-known dexamethasone corticosteroid with a 32 antiinflammatory ratio. The two most active compounds 4 b and 4 h showed IC 50 values more than 200 μM against the HepG2 cell line, in comparison with doxorubicin (IC 50 < 1 μM), indicated biocompatibility and nontoxic behavior. 4 d, 4 j, 4 k, and 4 l, were active against S. aureus and E. coli and had broad spectrum property. The tested compounds were subjected to in silico prediction of pharmacokinetics properties (ADMET) to assess the potential in vivo effectiveness. The molecular docking study confirmed that the active inhibitors 4 b and 4 h are well fitted in the iNOS active site. This data suggests that 4 b and 4 h could potentially serve as effective iNOS inhibitors, a represent promising lead compounds for treating inflammatory disorders.

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Cytotoxicity, anticancer, and antioxidant properties of mono and bis-naphthalimido β-lactam conjugates

Cited by 10 publications

References 58 publications

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Molecular Docking and Antibacterial Assessment of Monocyclic β‐Lactams against Broad‐Spectrum and Nosocomial Multidrug‐Resistant Pathogens

Sulfonamide‐β‐lactam Hybrids Incorporating the Piperazine Moiety as Potential Antiinflammatory Agent with Promising Antibacterial Activity

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