Design, Synthesis, &amp;lt;i&amp;gt;in Vitro&amp;lt;/i&amp;gt; Antibacterial Activity, and Docking Studies of New Rhodanine Derivatives

Abusetta, Aisha; Alumairi, Jowhara; Alkaabi, Mariam Y.; Ajeil, Ruba Al; Shkaidim, Asma Abu; Akram, Dana; Pajak, J.; Ghattas, Mohammad A.; Atatreh, Noor; AlNeyadi, Shaikha S.

doi:10.4236/ojmc.2020.101002

Cited by 10 publications

(10 citation statements)

References 28 publications

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“…From many years, it is been known that rhodanine and its derivatives possess a variety of activities, such as antibacterial, antiviral, anticonvulsant, antidiabetic, antihistaminic, anticancer and hypnotic [ 14 , 15 , 16 ].…”

Section: Discussionmentioning

confidence: 99%

Impact of Polyrhodanine Manganese Ferrite Binary Nanohybrids (PRHD@MnFe2O4) on Osteoblasts and Osteoclasts Activities—A Key Factor in Osteoporosis Treatment

et al. 2022

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Osteoporosis is characterized by the reduction of bone mineral density and the weakness of the bone strength leading to fractures. Searching for new compounds that stimulate bone activity and their ability to reconstruct seems to be a promising tool in osteoporosis treatment. Here, we performed analyses comparing the impact of polyrhodanine (PRHD) and its derivatives on the viability (anti-proliferative tests), morphology and mitochondrial network (confocal microscopy) towards pre-osteoblasts (MC3T3-E1 cell line) and osteoclasts (4B12 cell line). Moreover, we assessed the expression of genes associated with the apoptosis, inflammation and osteogenic differentiation by qPCR technique. Our results clearly demonstrated that PRHD and its modification at ratio 10/90 significantly improves the pre-osteoblast’s proliferative abilities, while reducing osteoclast function. The observed effects were strongly correlated with the cytoskeleton and mitochondrial network development and arrangement. Additionally, the expression profile of genes revealed enhanced apoptosis of osteoclasts in the case of PRHD and its modification at ratio 10/90. Moreover, in this case we also observed strong anti-inflammatory properties demonstrated by decreased expression of Il1b, Tnfa and Tgfb in pre-osteoblasts and osteoclasts. On the other hand, enhanced expression of the markers associated with bone remodeling, namely, osteopontin (OPN), osteocalcin (OCL) and alkaline phosphatase (ALP), seem to confirm the role of PRHD@MnFe2O4 in the promotion of differentiation of pre-osteoblasts through the ALP-OPN-OCL axis. Based on these observations, PRHD@MnFe2O4 could be a potential agent in osteoporosis treatment in future, however, further studies are still required.

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Section: Discussionmentioning

confidence: 99%

Impact of Polyrhodanine Manganese Ferrite Binary Nanohybrids (PRHD@MnFe2O4) on Osteoblasts and Osteoclasts Activities—A Key Factor in Osteoporosis Treatment

et al. 2022

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“…In addition, 2 hodamine derivatives demonstrate a broad spectrum of pharmacological activities, such as antimicrobial [ 6 , 7 , 8 , 9 ], anticancer [ 10 , 11 , 12 ], anti-HIV [ 13 , 14 ], anti-diabetic [ 15 , 16 ], anti-tubercular [ 17 ], and immunoproteasome inhibitory activity [ 18 ], suggesting that this scaffold occupies a vital position in drug discovery.…”

Section: Introductionmentioning

confidence: 99%

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

et al. 2023

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Herein, we report the experimental evaluation of the antimicrobial activity of seventeen new (Z)-methyl 3-(4-oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylate derivatives. All tested compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin as well as streptomycin by 10–50 fold. The most sensitive bacterium was En. Cloacae, while E. coli was the most resistant one, followed by M. flavus. The most active compound appeared to be compound 8 with MIC at 0.004–0.03 mg/mL and MBC at 0.008–0.06 mg/mL. The antifungal activity of tested compounds was good to excellent with MIC in the range of 0.004–0.06 mg/mL, with compound 15 being the most potent. T. viride was the most sensitive fungal, while A. fumigatus was the most resistant one. Docking studies revealed that the inhibition of E. coli MurB is probably responsible for their antibacterial activity, while 14a–lanosterol demethylase of CYP51Ca is involved in the mechanism of antifungal activity. Furthermore, drug-likeness and ADMET profile prediction were performed. Finally, the cytotoxicity studies were performed for the most active compounds using MTT assay against normal MRC5 cells.

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“…Some of them have also shown inhibitory potential against Gramnegative organisms viz., P. aeruginosa, E. coli etc. Rhodanine and its derivatives are reported to alter vital functions involved in bacterial growth such as DNA Gyrase B, [10,11] metallo-β-lactamases, [12,13] penicillin binding protein (PBP), [14] Mur ligases, [15] RNA polymerase, [16] Enoyl ACP reductases, [17] 1-deoxy-dxylulose-5-phosphate reductoisomerase (DXR) [18] etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of Rhodanine and Its Related Heterocyclic Compounds against S. aureus and A. baumannii

Akunuri

Kaul

et al. 2022

Chemistry & Biodiversity

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Antimicrobial resistance is a serious challenge to modern medicine. Besides imposing high financial burden, multidrug resistant infections are directly responsible for high morbidity and mortality. Even though a number of antibiotics are currently available to treat infections caused by ESKAPE organisms, more and more bacterial strains are becoming resistant to these drugs. Prevailing circumstances pose an urgent unmet need for the development of newer antimicrobials to treat the infections caused by MDR organisms. Rhodanine and structurally related 5‐membered heterocycles possess wide range of pharmacological activities. A number of these derivatives have shown good to potent inhibition against various microorganisms. They are reported to alter the function of DNA gyrase B, metallo‐β‐lactamases, penicillin binding protein (PBP), Mur ligases, RNA polymerase, Enoyl ACP reductases, 1‐deoxy‐d‐xylulose‐5‐phosphate reductoisomerase. etc which are vital in bacterial growth, survival and replication. In this study, we have generated a library of Rhodanine and related 5 membered heterocyclic derivatives and screened them against a panel of pathogens. Among all the compounds, 2a–i, 3a–b, 3g, 4, 6b–c, 6e, 6g, 12a–b and 14b–c have demonstrated good to moderate inhibition against S. aureus (MIC 0.125–8 μg/mL). Further, compound 17b demonstrated moderate activity against A. baumannii (MIC 8 μg/mL). In addition, compounds 2a, 2e, 4, 6c, 6g and 14b have shown good to mild inhibition against MDR S. aureus including VRSA (MIC 0.5–16 μg/mL) with good selectivity index 20–1600. In addition, compound 2e inhibited the growth gradually after 6 h in time kill kinetic studies and not antagonized with the tested FDA approved drugs.

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Design, Synthesis, <i>in Vitro</i> Antibacterial Activity, and Docking Studies of New Rhodanine Derivatives

Cited by 10 publications

References 28 publications

Impact of Polyrhodanine Manganese Ferrite Binary Nanohybrids (PRHD@MnFe2O4) on Osteoblasts and Osteoclasts Activities—A Key Factor in Osteoporosis Treatment

Impact of Polyrhodanine Manganese Ferrite Binary Nanohybrids (PRHD@MnFe2O4) on Osteoblasts and Osteoclasts Activities—A Key Factor in Osteoporosis Treatment

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

Synthesis and Antibacterial Evaluation of Rhodanine and Its Related Heterocyclic Compounds against S. aureus and A. baumannii

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