Novel plastoquinone analogs containing benzocaine and its analogs: structure‐based design, synthesis, and structural characterization

Bayrak, Nilüfer; Yıldız, Mahmut; Yıldırım, Hatice; Mataracı-Kara, Emel; Tuyun, Amaç Fatih

doi:10.1007/s11164-020-04384-5

Cited by 11 publications

(17 citation statements)

References 44 publications

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“…A key aspect of the biological activity in our previous studies is the certain chemical modifications of 1,4-quinone moiety. Naphthoquinones [ 19 , 32 , 33 , 34 , 35 ], quinolinequinones [ 27 , 30 , 36 , 37 ], and dimethylbenzoquinones [ 28 , 38 , 39 ] are the most widely used motifs belonging to the quinone family, being biologically important lead structures, which have been extensively used over the years [ 40 , 41 ]. Some of these C2- and/or C2C3-thiolated 1,4-quinones with different side groups were more potent than the reference drug(s).…”

Section: Introductionmentioning

confidence: 99%

“…Some of these C2- and/or C2C3-thiolated 1,4-quinones with different side groups were more potent than the reference drug(s). In these studies, alkyl chain thiols were connected to a dichloronaphthoquinone [ 32 , 33 ] and dimethylbenzoquinone [ 28 , 38 , 39 , 42 ] via different substrates [ 30 , 31 ]. As seen in these studies, the used alkyl chain or aromatic thiols as substrates, connected to dimethylbenzoquinone, did not exhibit any significant antibacterial and/or antifungal activity.…”

Section: Introductionmentioning

confidence: 99%

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Promising Antibacterial and Antifungal Agents Based on Thiolated Vitamin K3 Analogs: Synthesis, Bioevaluation, Molecular Docking

et al. 2022

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In the present study, we designed and synthesized thiolated VK3 analogs (VK3a–g) along with an extensive antimicrobial study. After the evaluation of the antibacterial and antifungal activity against various bacterial and fungal strains, we presented an initial structure–activity relationship study on these VK3 analogs. In particular, four thiolated VK3 analogs exhibited superior biological potency against some Gram-positive bacterial strains, including Staphylococcus aureus (ATCC® 29213) and Enterococcus faecalis (ATCC® 29212). Next, all thiolated VK3 analogs were evaluated for their potential of cell growth inhibition on the NCI-60 cancer cell lines panel. This screening underlined that the thiolated VK3 analogs have no visible cytotoxicity on different cancer cell lines. The selected two thiolated VK3 analogs (VK3a and VK3b), having minimal hemolytic activity, which also have the lowest MIC values on S. aureus and E. faecalis, were further evaluated for their inhibition capacities on biofilm formation after evaluating their potential in vitro antimicrobial activity against each of the 20 clinically obtained resistant strains of Staphylococcus aureus. VK3b showed excellent antimicrobial activity against clinically resistant S. aureus isolates. Furthermore, the tested molecules showed nearly two log10 reduction in the viable cell count at six hours according to the time kill curve studies. Although these molecules decreased biofilm attachment about 50%, when sub-MIC concentrations were used these molecules increased the percentage of biofilm formation. The molecular docking of VK3a and VK3b in S. aureus thymidylate kinase was conducted in order to predict their molecular interactions. VK3a and VK3b exhibited excellent lead-likeness properties and pharmacokinetic profiles that qualify them for further optimization and development. In conclusion, since investigating efficient novel antimicrobial molecules is quite difficult, these studies are of high importance, especially in the present era of antimicrobial resistance.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Promising Antibacterial and Antifungal Agents Based on Thiolated Vitamin K3 Analogs: Synthesis, Bioevaluation, Molecular Docking

et al. 2022

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“…The consciousness of “round sky and place” can also be seen everywhere in life, which is also the popularization and development of circular elements. The simple simplification, multichange, perfection, resonance, and other characteristics can be accepted by everyone, and new laws can be found from these morphological laws, such as the design of the temple of heaven and the temple of the earth [ 9 , 10 ]. It is precisely because these simple elements, such as squares and circles, gradually form complex cartoon images, so as to realize the design of visual elements in different animation character modeling design, such as the character's face, eyes, and other parts [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Multimedia Character Modeling Design and Modeling of Cartoon Animation Based on Bayesian Sequence Recommendation Algorithm

Wen

Yang

2022

Computational Intelligence and Neuroscience

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With the continuous development of the social economy, cartoon animation and other multimedia and streaming media forms are becoming more and more popular and are loved by all kinds of people, such as monkey king and Nezha. However, the multimedia of these cartoon animation needs to conform to mainstream values and transmit positive energy. In view of these needs and shortcomings, this study relies on the Bayesian sequence recommendation algorithm, combs the three-tier architecture diagram of multimedia character modeling, analyzes it, respectively, from the perspectives of hierarchy, behavior, and interactive process, and tries to build corresponding animation design management documents, so as to provide corresponding decision-making basis to produce animation and develop corresponding results, provide corresponding reference mode for cartoon animation multimedia character manufacturing, complete corresponding cartoon animation multimedia characters faster, and improve cartoon animation multimedia works and efficiency. The simulation results show that the Bayesian sequence recommendation algorithm is effective and can support the design and modeling of cartoon animation multimedia characters.

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“…Then, we concluded that the presence of alkoxy group(s) especially with a short chain contributed to the biological activities of the compounds. We also analyzed the effect of hydrogen and different halogen atoms such as bromine and chlorine on the biological activity of 2‐chloro‐3‐arylamino‐5,6‐dimethyl‐1,4‐benzoquinones (Bayrak et al, 2020, 2021). As in the case with literature, change of the chlorine atom with either bromine or hydrogen atom caused a decrease in the activity (Bayrak et al, 2020; Lawrence et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

“…especially with a short chain contributed to the biological activities of the compounds. We also analyzed the effect of hydrogen and different halogen atoms such as bromine and chlorine on the biological activity of 2-chloro-3-arylamino-5,6-dimethyl-1,4-benzoquinones (Bayrak et al, 2020(Bayrak et al, , 2021. As in the case with literature, change of the chlorine…”

Section: Introductionmentioning

confidence: 99%

Discovery and s tructure–activity relationships of the quinolinequinones: Promising antimicrobial agents and mode of action evaluation

et al. 2021

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In our pursuit of developing the novel, potent, and selective antimicrobial agents, we managed to obtain the quinolinequinone for their antimicrobial profile with minimal inhibitory concentrations (MICs) determined against a panel of seven bacterial strains (three gram-positive and four gram-negative bacteria) and three fungi. The structureactivity relationship (SAR) for the quinolinequinone class of antimicrobials was determined. Interestingly, QQ1, QQ4, QQ6-9, QQ12, and QQ13 displayed equal antibacterial potential against S. aureus (MIC = 1.22 mg/L), respectively, to the standard positive control Cefuroxime-Na. QQ10 had the best inhibitory activity with the MIC value of 1.22 mg/L (fourfold more potent compared to reference standard Clotrimazole) against Candida albicans. On the other hand, while QQ10 is not too effective against gram-positive bacteria as much as the other analogs, QQ10 was the most effective quinolinequinones against fungi. Selected quinolinequinones were further evaluated for the mode of action, using in vitro antibiofilm activity, bactericidal activity by using time-kill curve assay, antibiofilm activity, and potential antimicrobial activity against each of 32 clinically obtained resistant strains of Gram-positive Bacteria. The results also revealed that the QQ14 had specific antifungal activity against fungi in particular C. albicans. Our results clearly showed that quinolinequinones are much more active in the inhibition of the biofilm attachment process than the inhibition of mature biofilm formation. Thus, as treatment options are narrowing for Methicillin-resistant Staphylococcus spp., Vancomycin-resistant Staphylococcus spp. daily, the quinolinequinones reported herein display promise as the lead candidates for further clinical applications against serious infections.

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Novel plastoquinone analogs containing benzocaine and its analogs: structure‐based design, synthesis, and structural characterization

Cited by 11 publications

References 44 publications

Promising Antibacterial and Antifungal Agents Based on Thiolated Vitamin K3 Analogs: Synthesis, Bioevaluation, Molecular Docking

Promising Antibacterial and Antifungal Agents Based on Thiolated Vitamin K3 Analogs: Synthesis, Bioevaluation, Molecular Docking

Multimedia Character Modeling Design and Modeling of Cartoon Animation Based on Bayesian Sequence Recommendation Algorithm

Discovery and s tructure–activity relationships of the quinolinequinones: Promising antimicrobial agents and mode of action evaluation

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