Synthesis, Antimicrobial Activity and QSAR Studies of Some New Sparfloxacin Derivatives

Kumar, Ayush; Grewal, Ajmer Singh; Singh, Vikramjeet; Narang, Rakesh; Pandita, Deepti; Lather, Viney

doi:10.1007/s11094-018-1837-y

Cited by 19 publications

(5 citation statements)

References 19 publications

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“…As it can be noted, amoxicillin has the HOMO and LUMO located at different regions in the molecular structure. This behaviour in the frontier orbitals has already been reported before for antimicrobial [91,92], antimicrobial-like [93], and antiprotozoal compounds [94], asserting to be a fundamental molecular characteristic for antimicrobial activity.…”

Section: Minimum Molecular Structuressupporting

confidence: 81%

Predicting the Adsorption of Amoxicillin and Ibuprofen on Chitosan and Graphene Oxide Materials: A Density Functional Theory Study

et al. 2021

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The occurrence, persistence, and accumulation of antibiotics and non-steroidal anti-inflammatory drugs (NSAIDs) represent a new environmental problem due to their harmful effects on human and aquatic life. A suitable absorbent for a particular type of pollutant does not necessarily absorb other types of compounds, so knowing the compatibility between a particular pollutant and a potential absorbent before experimentation seems to be fundamental. In this work, the molecular interactions between some pharmaceuticals (amoxicillin, ibuprofen, and tetracycline derivatives) with two potential absorbers, chitosan and graphene oxide models (pyrene, GO-1, and coronene, GO-2), were studied using the ωB97X-D/6-311G(2d,p) level of theory. The energetic interaction order found was amoxicillin/chitosan > amoxicillin/GO-1 > amoxicillin/GO-2 > ibuprofen/chitosan > ibuprofen/GO-2 > ibuprofen/GO-1, the negative sign for the interaction energy in all complex formations confirms good compatibility, while the size of Eint between 24–34 kcal/mol indicates physisorption processes. moreover, the free energies of complex formation were negative, confirming the spontaneity of the processes. The larger interaction of amoxicillin GOs, compared to ibuprofen GOs, is consistent with previously reported experimental results, demonstrating the exceptional predictability of these methods. The second-order perturbation theory analysis shows that the amoxicillin complexes are mainly driven by hydrogen bonds, while van der Waals interactions with chitosan and hydrophobic interactions with graphene oxides are modelled for the ibuprofen complexes. Energy decomposition analysis (EDA) shows that electrostatic energy is a major contributor to the stabilization energy in all cases. The results obtained in this work promote the use of graphene oxides and chitosan as potential adsorbents for the removal of these emerging pollutants from water.

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Section: Minimum Molecular Structuressupporting

confidence: 81%

Predicting the Adsorption of Amoxicillin and Ibuprofen on Chitosan and Graphene Oxide Materials: A Density Functional Theory Study

et al. 2021

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“…More recently, the influence of the frontier orbital on biological activity has been taken into account. Studies have reported [16][17][18] the relationships between frontier orbitals and different biological activities such as antimicrobial [35][36][37][38], anticancer [39][40][41][42][43][44][45][46], antifungal [47][48][49], and cytotoxic [50][51][52][53] effects. Currently, this knowledge plays a pivotal role in the new-drug-design field [54].…”

Section: Molecular Orbitalsmentioning

confidence: 99%

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

2020

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Twenty-four cannabinoids active against MRSA SA1199B and XU212 were optimized at WB97XD/6-31G(d,p), and several molecular descriptors were obtained. Using a multiple linear regression method, several mathematical models with statistical significance were obtained. The robustness of the models was validated, employing the leave-one-out cross-validation and Y-scrambling methods. The entire data set was docked against penicillin-binding protein, iso-tyrosyl tRNA synthetase, and DNA gyrase. The most active cannabinoids had high affinity to penicillin-binding protein (PBP), whereas the least active compounds had low affinities for all of the targets. Among the cannabinoid compounds, Cannabinoid 2 was highlighted due to its suitable combination of both antimicrobial activity and higher scoring values against the selected target; therefore, its docking performance was compared to that of oxacillin, a commercial PBP inhibitor. The 2D figures reveal that both compounds hit the protein in the active site with a similar type of molecular interaction, where the hydroxyl groups in the aromatic ring of cannabinoids play a pivotal role in the biological activity. These results provide some evidence that the anti-Staphylococcus aureus activity of these cannabinoids may be related to the inhibition of the PBP protein; besides, the robustness of the models along with the docking and Quantitative Structure–Activity Relationship (QSAR) results allow the proposal of three new compounds; the predicted activity combined with the scoring values against PBP should encourage future synthesis and experimental testing.

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“…In the last twenty years, the frontier orbitals began to play a pivotal role in the medicinal chemistry field; the studies of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) have allowed the understanding of several biological activities, such as antimicrobial [ 62 , 63 , 64 , 65 ], anticancer [ 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 ], antifungal [ 74 , 75 , 76 ], and cytotoxicity [ 77 , 78 , 79 , 80 ]. More recently, the shape of frontier orbitals has been used to differentiate between active and inactive compounds against a specific disease [ 81 , 82 ].…”

Section: Resultsmentioning

confidence: 99%

In Silico Screening of the DrugBank Database to Search for Possible Drugs against SARS-CoV-2

2021

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Coronavirus desease 2019 (COVID-19) is responsible for more than 1.80 M deaths worldwide. A Quantitative Structure-Activity Relationships (QSAR) model is developed based on experimental pIC50 values reported for a structurally diverse dataset. A robust model with only five descriptors is found, with values of R2 = 0.897, Q2LOO = 0.854, and Q2ext = 0.876 and complying with all the parameters established in the validation Tropsha’s test. The analysis of the applicability domain (AD) reveals coverage of about 90% for the external test set. Docking and molecular dynamic analysis are performed on the three most relevant biological targets for SARS-CoV-2: main protease, papain-like protease, and RNA-dependent RNA polymerase. A screening of the DrugBank database is executed, predicting the pIC50 value of 6664 drugs, which are IN the AD of the model (coverage = 79%). Fifty-seven possible potent anti-COVID-19 candidates with pIC50 values > 6.6 are identified, and based on a pharmacophore modelling analysis, four compounds of this set can be suggested as potent candidates to be potential inhibitors of SARS-CoV-2. Finally, the biological activity of the compounds was related to the frontier molecular orbitals shapes.

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Synthesis, Antimicrobial Activity and QSAR Studies of Some New Sparfloxacin Derivatives

Cited by 19 publications

References 19 publications

Predicting the Adsorption of Amoxicillin and Ibuprofen on Chitosan and Graphene Oxide Materials: A Density Functional Theory Study

Predicting the Adsorption of Amoxicillin and Ibuprofen on Chitosan and Graphene Oxide Materials: A Density Functional Theory Study

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

In Silico Screening of the DrugBank Database to Search for Possible Drugs against SARS-CoV-2

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