Synthesis and In vitro Biological Evaluation of Quinolone-Based Hydrazones as Potential Antidiabetic Agents Targeting Key Metabolic Enzymes Article Swipe
Naik Jui Pravin
,
Rohini S. Kavalapure
,
Shankar Gharge
,
Shankar G. Alegaon
,
Shriram D. Ranade
,
Ling Shing Wong
,
Ramith Ramu
,
C. Ramya
·
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1021/acsomega.5c04663
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1021/acsomega.5c04663
A series of novel structures featuring quinolone-based hydrazones (5a-5q) were synthesized, characterized, and screened for their potential inhibition of key enzymes involved in carbohydrate metabolism, namely human pancreatic α-amylase (HPA) and human lysosomal acid α-glucosidase, as well as aldose reductase, an enzyme associated with diabetes-related complications. The synthesized compounds exhibited a broad range of inhibitory activities against both α-glucosidase (IC50: 7.44 ± 0.07 to 14.75 ± 0.15 μg/mL) and α-amylase (IC50: 21.05 ± 0.17 to 31.43 ± 0.11 μg/mL). Notably, compound 5o (5-nitrofuran) demonstrated the most potent inhibition against both enzymes (α-glucosidase IC50 = 7.44 ± 0.07 μg/mL; α-amylase IC50 = 21.05 ± 0.17 μg/mL), surpassing the standard drug acarbose. Furthermore, these hydrazones also showed promising aldose reductase inhibitory activities (IC50: 4.12 ± 0.09 to 11.00 ± 0.05 μg/mL), with compound 5o again exhibiting the highest potency (IC50 = 4.12 ± 0.09 μg/mL), even outperforming quercetin. Kinetic studies on 5o revealed a reversible, noncompetitive inhibition mechanism against aldose reductase with an inhibition constant (K i) of 4.65 μM. Molecular docking studies against α-amylase, α-glucosidase, and aldose reductase demonstrated favorable binding interactions for several compounds, with 5o showing particularly strong interactions with the active site of aldose reductase (docking score: -10.051). Molecular dynamics simulations of the 5o-aldose reductase complex over 100 ns confirmed stable binding within the active site. Density functional theory (DFT) analysis of 5o revealed a small HOMO-LUMO energy gap (0.112566 eV) and a soft nature, suggesting good chemical reactivity. These findings showcase the potential of quinolone-based hydrazones, particularly compound 5o, as promising candidates aiming at the development of multitarget therapies for antidiabetic agents.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acsomega.5c04663
- OA Status
- gold
- References
- 46
- Related Works
- 10
- OpenAlex ID
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- OpenAlex ID
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https://openalex.org/W4412572143Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/acsomega.5c04663Digital Object Identifier
- Title
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Synthesis and In vitro Biological Evaluation of Quinolone-Based Hydrazones as Potential Antidiabetic Agents Targeting Key Metabolic EnzymesWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2025Year of publication
- Publication date
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2025-07-22Full publication date if available
- Authors
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Naik Jui Pravin, Rohini S. Kavalapure, Shankar Gharge, Shankar G. Alegaon, Shriram D. Ranade, Ling Shing Wong, Ramith Ramu, C. RamyaList of authors in order
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https://doi.org/10.1021/acsomega.5c04663Publisher landing page
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YesWhether a free full text is available
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goldOpen access status per OpenAlex
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https://doi.org/10.1021/acsomega.5c04663Direct OA link when available
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Quinolone, In vitro, Key (lock), Enzyme, Chemistry, Pharmacology, Combinatorial chemistry, Computational biology, Biochemistry, Biology, Antibiotics, EcologyTop concepts (fields/topics) attached by OpenAlex
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0Total citation count in OpenAlex
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10Other works algorithmically related by OpenAlex
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