Mutual Prodrugs of Piroxicam

Imran, Mohd; Asif, Mohammad

doi:10.31080/asps.2019.03.0305

Cited by 5 publications

(2 citation statements)

References 4 publications

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“…The antibacterial properties of different phthalimide derivatives of N-alkyl, N-alkyloxy, N-acyl, butyl, and N-hydroxyl have been reported against both Gram-positive ( Streptococcus pneumoniae , Micrococcus luteus , and Listeria monocytogenes) and Gram-negative ( Pseudomonas aeruginosa , Salmonella typhimurium , and Escherichia coli) bacterial strains which have shown promising results because of their smaller size and high potency in disease control management ( Othman et al, 2019 ). Similarly, the derivatives of chiral phthalimides with N-alkyloxy and N-alkyl substitution in combination with maleimide have shown antifungal activity against fungi ( Candida albicans and Aspergillus fumigatus) ( Imran et al, 2019 ). One of the reasons for inflammatory diseases is the denaturation of the protein present in tissues that leads to the development of autoantigens.…”

Section: Introductionmentioning

confidence: 99%

Chiral phthalimides against penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus: molecular docking and in vitro analysis

Khan,

Khan

et al. 2024

Front. Pharmacol.

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Staphylococcus aureus (S. aureus) is a commensal bacterium and an opportunistic pathogen causing a wide variety of infections ranging from localized skin and soft tissue infections to life-threatening severe bacteremia, osteomyelitis, endocarditis, atopic dermatitis, prosthetic joint infection, staphylococcal food poisoning, medical device-related infections, and pneumonia. It is attributed to an acquired resistant gene, mecA, encoding penicillin-binding protein 2a (PBP2a). PBP2a is an essential protein responsible for the resistivity of methicillin-resistant S. aureus (MRSA) to various beta-lactam antibiotics. The antimicrobial treatment alternatives for MRSA are increasingly limited. Therefore, developing alternative therapeutic options for its treatment is the need of the day. Phthalimides and their N-substituted derivatives are of biological importance as they possess extensive biological and pharmaceutical properties and can serve as an excellent therapeutic option for MRSA. This study uses three chiral phthalimides (FIA, FIB, and FIC) to check their in silico and in vitro inhibitory effects. Molecular docking of these chiral phthalimides against PBP2a of MRSA was performed initially. After promising results, these novel compounds were screened through the agar-well diffusion method and micro-broth dilution assay to investigate their in vitro inhibitory activities with FIB being the strongest anti-staphylococcal agent yielding a 21 mm zone of inhibition and a minimum inhibitory concentration (MIC) of 0.022 ug, respectively. The zones of inhibition obtained through the in vitro activity showed that these chiral phthalimides possess substantial anti-MRSA activities and have the potential to be considered as alternative chemotherapeutics to treat the infections caused by MRSA after the confirmation of their cytotoxic and pharmacokinetic studies.

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Section: Introductionmentioning

confidence: 99%

Chiral phthalimides against penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus: molecular docking and in vitro analysis

Khan,

Khan

et al. 2024

Front. Pharmacol.

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“…The free carboxylic group of the NSAID was condensed with another pharmacologically active drug. To name a few mutual prodrugs, Mefenamic acid-PGA to overcome poor solubility 12 , Etodolic and Thymol with reduced ulcerogenic activity 13 , Piroxican with Aceclofenac, Ibuprofen and Mefenamic acid to reduce gastric side effects 14 , esters of Mefenamic acid with thymol and sesamol with enhanced antiinflammatory activity and reduced gastric toxicity 15 , Mefenamic acid with a tocopherol and a tocopherol acetate to reduce the CNS toxicity and enhance therapeutic efficacy 16 , Galifloxacin -Paracetamol to enhance therapeutic action 17 , p-Aminosalicyclic acid and alkyl, alkoxy carbonyl to increase oral bioavailability 18 , xylitol-ibuprofen ester for enhanced water solubility 19 , Ibuprofensulphanilamide with an improved toxicity profile 20 . NSAIDs with 4-(1H-benzo[d] imidazole 2-yl)phenol (BZ) with better anti-inflammatory potential 21 , Febuxostat-NSAIDs with gastrointestinal safety profile 22 .…”

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confidence: 99%

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2023

IJPSR

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Inflammation and pain have all been successfully treated using nonsteroidal anti-inflammatory drugs. Today's nonsteroidal anti-inflammatory drugs (NSAIDs) are typically taken with restriction due to the gastric intolerance they create. The prodrug approach is quite effective in reducing the side effects caused by NSAIDs. Many nonsteroidal anti-inflammatory drug molecules have been modified in several ways so that they can be less hazardous to the stomach. Using the mutual prodrug concept, the side effects can be minimized by covalently bonding the NSAIDs to the second pharmacologically active carrier. The goal of the current study is to use the coupling approach to create mutual ester prodrugs of NSAIDs (MS and MP) in order to overcome the troubles, they cause, like gastrointestinal toxicity, ulcerogenic side effects, etc. The prodrugs were made by using a better reagent, EDAC 1-Ethyl-3-(3-Dimethylaminopropyl) carbodiimide hydrochloride, because it outperformed DCC (N, N′-Dicyclohexylcarbodiimide) as a coupling agent. The physiochemical properties were determined, and the structures of the synthesized prodrugs were confirmed and analyzed by UV, FT-IR, 1 HNMR, 13 CNMR Spectroscopy and Mass spectrometry. INTRODUCTION:The clinical importance of NSAIDs is enormous, but there's a robust risk that they might have negative effects on the abdomen. The ability of NSAIDs to restrict the activity of the enzyme cyclooxygenase (COX) involved in prostaglandin H 2 (PGH 2 ) production is correlated with their pharmacological effectiveness 1, 2 . It is generally known that COX has two isoforms, COX-I and COX-II, which are controlled in various ways. In the GIT, COX-I is expressed constitutively in the stomach to provide cytoprotection, and COX-II plays a major role in the biosynthesis of prostaglandin, which is expressed in inflammatory cell 3 .

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DFT Calculations in Monomeric and Dimeric Forms of N-Benzylmaleimide (Nbm) Combined With Vibrational Spectroscopic Parameters

Arı

2023

Eskişehir Teknik Üniversitesi Bilim Ve Teknoloji Dergisi B - Teorik Bilimler

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The structural, vibrational and theoretical analyses of N-benzylmaleimide (NBM) having chemical and biological significances have been made. The four possible conformers and their sixty-six dimeric forms linked by the intermolecular C=O···H hydrogen bonding were investigated for the stability. The conformational and the dimeric structures of NBM in the gas phase were investigated and the population distributions of the conformations and dimers were obtained using the Boltzmann distribution. The experimental IR and Raman spectra of solid phase NBM were recorded, and the bands were compared with the theoretical wavenumber the values of the monomer and the dimer forms for their assignments. The new scale factors (0.9617 for B3LYP/6-31G(d) and 0.9531 for M06-2X/6-31G(d)) obtained for NBM can be used more accurately in vibration calculations of all maleimide derivatives. The Molecular Electrostatic Potential (MEP) map showed that the negative and the positive regions have changed from monomeric to dimeric form changes, while the HOMO-LUMO shapes did not generally change in monomeric and dimeric forms. The nucleophilic and electrophilic Fukui functions and dual descriptors shows that maleimide and benzyl groups are nucleophilic and electrophilic regions, respectively, additionally the dual descriptor values decrease upon dimerization.

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Mutual Prodrugs of Piroxicam

Cited by 5 publications

References 4 publications

Chiral phthalimides against penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus: molecular docking and in vitro analysis

Chiral phthalimides against penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus: molecular docking and in vitro analysis

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DFT Calculations in Monomeric and Dimeric Forms of N-Benzylmaleimide (Nbm) Combined With Vibrational Spectroscopic Parameters

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