Exploration of synthetic antioxidant flavonoid analogs as acetylcholinesterase inhibitors: an approach towards finding their quantitative structure–activity relationship

Karmakar, Abhijit; Ambure, Pravin; Mallick, Tamanna; Das, Shantanu; Roy, Kunal; Begum, Naznin Ara

doi:10.1007/s00044-019-02330-8

Cited by 31 publications

(12 citation statements)

References 45 publications

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“…Furthermore, compounds f12a–f13c presented an OH group signal at 9.60–9.30 ppm, indicating the loss of 2-hydroxy from the starting material (chalcone), classically observed with a larger chemical shift due to the intramolecular H bond with the carbonyl group. The NMR data were compared with the literature, and the structures of the synthesised compounds were confirmed [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. The spectra are available in the Supplementary Material .…”

Section: Resultsmentioning

confidence: 99%

Flavonoid Derivatives as New Potent Inhibitors of Cysteine Proteases: An Important Step toward the Design of New Compounds for the Treatment of Leishmaniasis

et al. 2023

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Leishmaniasis is a neglected tropical disease, affecting more than 350 million people globally. However, there is currently no vaccine available against human leishmaniasis, and current treatment is hampered by high cost, side-effects, and painful administration routes. It has become a United Nations goal to end leishmaniasis epidemics by 2030, and multitarget drug strategy emerges as a promising alternative. Among the multitarget compounds, flavonoids are a renowned class of natural products, and a structurally diverse library can be prepared through organic synthesis, which can be tested for biological effectiveness. In this study, we synthesised 17 flavonoid analogues using a scalable, easy-to-reproduce, and inexpensive method. All synthesised compounds presented an impressive inhibition capacity against rCPB2.8, rCPB3, and rH84Y enzymes, which are highly expressed in the amastigote stage, the target form of the parasite. Compounds 3c, f12a, and f12b were found to be effective against all isoforms. Furthermore, their intermolecular interactions were also investigated through a molecular modelling study. These compounds were highly potent against the parasite and demonstrated low cytotoxic action against mammalian cells. These results are pioneering, representing an advance in the investigation of the mechanisms behind the antileishmanial action of flavonoid derivatives. Moreover, compounds have been shown to be promising leads for the design of other cysteine protease inhibitors for the treatment of leishmaniasis diseases.

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Section: Resultsmentioning

confidence: 99%

Flavonoid Derivatives as New Potent Inhibitors of Cysteine Proteases: An Important Step toward the Design of New Compounds for the Treatment of Leishmaniasis

et al. 2023

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“…Flavonoids are polyphenolic molecules known for their antioxidant and anti‐inflammatory health benefits. The flavonoids provide protection to the living systems by stabilizing the free radicals (Karmakar et al, 2019). The content of flavonoid was estimated from the QT standard curve and results were stated as QE/mg (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

Scanning electron microscopy of Sophora alopecuroides L. seeds and their cytotoxic, antimicrobial, antioxidant, and enzyme inhibition potentials

Zahra

Iqbal

Abbasi

et al. 2021

Microscopy Res & Technique

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Sophora alopecuroides L. is a highly medicinal plant. The aim of the current study was to determine the phytochemical screening, pharmacological potentials and application of scanning electron microscope (SEM) of S. alopecuroides (SA) seeds. To achieve this purpose, six different solvents were used to prepare SA seed extracts. Phytochemical and antioxidant activities were determined calorimetrically. To investigate the antidiabetic activity, α-amylase inhibition assay was determined. Brine shrimp assay was used to determine cytotoxicity potential. Anti-leishmanial potential was confirmed using MTT assay. Disc-diffusion method was used to detect protein kinase inhibitory, antibacterial and antifungal activities and showed significant results. SEM analysis was used as an identification tool. Considerable amount of phenolic and flavonoid contents were identified in methanol extract (SASM) (93.76 ± 2.71 GAE/mg) and (77 ± 3.60 QE/mg). Highest DPPH scavenging potential (82%) was reported for SASM. Significant total antioxidant capacity (90.60 ± 1.55 alpha amylase enzyme [AAE]/mg) and total reducing power (94.44 ± 1.38 AAE/mg) were determined for LOSM. Highest α-amylase inhibition was reported in SASM (78.20 ± 1.58%). Highest LD 50 of brine shrimp was found for n-hexane extract (SASH) 13.03 μg/ml. All extracts showed strong anti-leishmanial activity except SASH. The seeds of SA were seen to be oblong to obovate, projections, wavy slightly straight, anticlinal wall was raised with apex acuminate. In conclusion, our experimental findings highly support the ethnomedicinal and biological potentials of the SA seeds. Moreover, SA seeds need to be explored for identification and isolation of bioactive compounds. In future, we recommend further in vivo toxicity assays and clinical efficacies to further evaluate its different biomedical properties.

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“…Furthermore, compounds f12a-f13c presented a signal of the OH group in 9.60 -9.30, indicating the loss of 2-hydroxy from their starting material (chalcone), classically observed in larger chemical shift due to the intramolecular H bond with the carbonyl group. The NMR data was compared with those of the literature and the structures of the synthesized compounds were confirmed [25][26][27][28][29][30][31][32][33][34][35][36][37]. The spectra are available in the Supplementary material.…”

Section: Chemistrymentioning

confidence: 95%

Flavonoid Derivatives as New Potent Inhibitors of Cysteine Proteases: An Important Step toward the Design of New Compounds for the Treatment of Leishmaniasis

Lourenço¹,

Iório²,

Silva³

et al. 2022

Preprint

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Leishmaniasis is a neglected tropical disease and affects more than 350 million people worldwide. However, there are no vaccines for humans, and current treatment is hampered due to its high cost, numerous side effects, and painful administration routes. Ending its epidemics by 2030 has become a United Nations goal, and the multitarget drug strategy emerges as a promising alternative. Flavonoids are an example of multitarget compounds and organic synthesis represents a tool to obtain high yields of these molecules. In our study, we synthesized 17 flavonoid analogs using a scalable, easy-to-reproduce, and inexpensive method. All compounds demonstrated an impressive inhibition capacity against rCPB2.8, rCPB3, and rH84Y, which are highly expressed in the amastigote stage, the target form of the parasite. Compounds 3c, f12a, and f12b stood out as effective against all isoforms and intermolecular interactions were investigated through a molecular modeling study. The compounds were highly potent against the parasite and demonstrated low cytotoxic action against mammalian cells. The results were pioneering, representing an advance in the investigation of the mechanisms behind the antileishmanial action of flavonoid derivatives. Furthermore, compounds have shown to be promising leads for the design of other cysteine protease inhibitors for the treatment of leishmaniasis diseases.

show abstract

Exploration of synthetic antioxidant flavonoid analogs as acetylcholinesterase inhibitors: an approach towards finding their quantitative structure–activity relationship

Cited by 31 publications

References 45 publications

Flavonoid Derivatives as New Potent Inhibitors of Cysteine Proteases: An Important Step toward the Design of New Compounds for the Treatment of Leishmaniasis

Flavonoid Derivatives as New Potent Inhibitors of Cysteine Proteases: An Important Step toward the Design of New Compounds for the Treatment of Leishmaniasis

Scanning electron microscopy of Sophora alopecuroides L. seeds and their cytotoxic, antimicrobial, antioxidant, and enzyme inhibition potentials

Flavonoid Derivatives as New Potent Inhibitors of Cysteine Proteases: An Important Step toward the Design of New Compounds for the Treatment of Leishmaniasis

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