Identification of potential urease inhibitors and antioxidants based on saccharin derived analogs: Synthesis, in vitro, and in silico studies

Ata, Amber; Salar, Uzma; Saleem, Faiza; Lateef, Mehreen; Khan, Salman Ali; Khan, Khalid Mohammed; Taha, Muhammad; Haider, Syed Moazzam; Ul-Haq, Zaheer

doi:10.1016/j.molstruc.2022.134376

Cited by 3 publications

(2 citation statements)

References 41 publications

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“…The 3D structure was then energy minimized using MMFF94x force field implemented in MOE. For α-amylase, the binding site was defined by selecting the coordinates of the cocrystallized ligand, while for α-glucosidase, we applied a previously established protocol. , PTOX was docked into the binding site of both the target protein using a triangular matcher as a placement method with an induced-fit docking protocol. The resultant poses were analyzed using Chimera software.…”

Section: Methodsmentioning

confidence: 99%

PEGylated Graphene Oxide as a Nanodrug Delivery Vehicle for Podophyllotoxin (GO/PEG/PTOX) and In Vitro α-Amylase/α-Glucosidase Inhibition Activities

Islam

Khan

et al. 2023

ACS Omega

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This study aims to develop a nanodrug delivery system containing podophyllotoxin (PTOX), a known anticancer drug, loaded on graphene oxide (GO). The system’s ability to inhibit α-amylase and α-glucosidase enzymes was also investigated. PTOX was isolated from Podophyllum hexandrum roots with a yield of 2.3%. GO, prepared by Hummer’s method, was converted into GO-COOH and surface-mobilized using polyethylene glycol (PEG) (1:1) in an aqueous medium to obtain GO-PEG. PTOX was loaded on GO-PEG in a facile manner with a 25% loading ratio. All the samples were characterized using FT-IR spectroscopy, UV/visible spectroscopy, and scanning electron microscopy (SEM). In FT-IR spectral data, GO-PEG-PTOX exhibited a reduction in acidic functionalities and there was an appearance of the ester linkage of PTOX with GO. The UV/visible measurements suggested an increase of absorbance in 290–350 nm regions for GO-PEG, suggesting the successful drug loading on its surface (25%). GO-PEG-PTOX exhibited a rough, aggregated, and scattered type of pattern in SEM with distinct edges and binding of PTOX on its surface. GO-PEG-PTOX remained potent in inhibiting both α-amylase and α-glucosidase with IC50 values of 7 and 5 mg/mL, closer to the IC50 of pure PTOX (5 and 4.5 mg/mL), respectively. Owing to the 25% loading ratio and 50% release within 48 h, our results are much more promising. Additionally, the molecular docking studies confirmed four types of interactions between the active centers of enzymes and PTOX, thus supporting the experimental results. In conclusion, the PTOX-loaded GO nanocomposites are promising α-amylase- and α-glucosidase-inhibitory agents when applied in vitro and have been reported for the first time.

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Section: Methodsmentioning

confidence: 99%

PEGylated Graphene Oxide as a Nanodrug Delivery Vehicle for Podophyllotoxin (GO/PEG/PTOX) and In Vitro α-Amylase/α-Glucosidase Inhibition Activities

Islam

Khan

et al. 2023

ACS Omega

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“…The saccharin moiety can be found not only in multifunctional luminescent materials [4], antioxidants [5], but mainly in diverse compounds exhibiting a broad spectrum of biological activities, such as antibacterial [6], analgesic [7], antitumor [8], inhibitors of acetylcholin‐esterase [9], rhomboid proteases [10] and human leukocyte elastase [11], among others. Notable examples are shown in Figure 1 and include ipsapirone, an anxiolytic and an antidepressant drug [12]; supidimide, a non‐teratogenic analogue of thalidomide used as a sedative [13]; SCP‐1, an acetaminophen derivative with analgesic properties [7]; repinotan, a 5HT 1A agonist used to treat patients with severe traumatic brain injury and ventilatory depression [14]; the pseudo‐peptide 1 , which has demonstrated inhibitory activity against HIV‐1 protease [15]; and the oxicam scaffold 2 , a ring system present in diverse compounds with anti‐inflammatory properties [16].…”

Section: Introductionmentioning

confidence: 99%

The Ritter reaction of N‐(hydroxymethyl)saccharin with nitriles

de Oliveira,

de Mattos

2023

Journal of Heterocyclic Chem

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The development of the Ritter reaction of N‐(hydroxymethyl)saccharin with nitriles for the synthesis of N‐[(saccharinyl)methyl]amides is reported. The success of this reaction relies on an operationally simple procedure and on the use of inexpensive reagents. The present method enables access to a variety of saccharin scaffolds of potential interest in medicinal chemistry in moderate to high yields. Furthermore, the scalability of this reaction was demonstrated by a multigram‐scale transformation, without any loss of efficiency.

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Assembly of Functionalized 3,4‐Fused Tricyclic Benzosultams via Radical‐Promoted Cascade Reactions

Reddy,

Kumari,

Sagar

et al. 2024

Adv Synth Catal

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Identification of potential urease inhibitors and antioxidants based on saccharin derived analogs: Synthesis, in vitro, and in silico studies

Cited by 3 publications

References 41 publications

PEGylated Graphene Oxide as a Nanodrug Delivery Vehicle for Podophyllotoxin (GO/PEG/PTOX) and In Vitro α-Amylase/α-Glucosidase Inhibition Activities

PEGylated Graphene Oxide as a Nanodrug Delivery Vehicle for Podophyllotoxin (GO/PEG/PTOX) and In Vitro α-Amylase/α-Glucosidase Inhibition Activities

The Ritter reaction of N‐(hydroxymethyl)saccharin with nitriles

Assembly of Functionalized 3,4‐Fused Tricyclic Benzosultams via Radical‐Promoted Cascade Reactions

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