Novel 3,19-(N-Phenyl-3-(4-fluorophenyl)-pyrazole) Acetal of Andrographolide Promotes Cell Cycle Arrest and Apoptosis in MDA-MB-231 Breast Cancer Cells Article Swipe
Siva Kumar Rokkam
,
Shahjalal Chowdhury
,
Yashwanth Inabathina
,
Lakshminath Sripada
,
Srinivas Nanduri
,
Balasubramanyam Karanam
,
Nageswara Rao Golakoti
·
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.3390/ph18071026
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.3390/ph18071026
Background: Natural products play a crucial role in cancer treatment due to their ability to selectively target cancer cells. Andrographolide, a major constituent of Andrographis paniculata, exhibits potential anticancer properties. Considering the pharmacological importance of nitrogen-based heteroaromatic scaffolds, particularly pyrazole motifs, this study aimed to integrate the pyrazole pharmacophore with the andrographolide scaffold to develop novel therapeutic candidates. Methods: Twenty novel 3,19-(N-phenyl-3-aryl-pyrazole) acetals of andrographolide and isoandrographolide were synthesized and characterized using UV-Vis, FT-IR, NMR, and HRMS. Initial anticancer screening was conducted by the National Cancer Institute (NCI), USA, against 60 human cancer cell lines. The most promising compound, 1f (R = 4-F), was selected for further biological evaluation in the MDA-MB-231 breast cancer cell line. Results: The MTT assay results demonstrated that compound 1f exhibited strong, dose-dependent anti-proliferative effects. The apoptosis analysis of 1f revealed a time-dependent increase in apoptotic cells, and cell cycle studies indicated S phase arrest in MDA-MB-231 cells. Antioxidant activity via the DPPH assay identified compounds 1b (R = 3-NO2) and 2b (R = 3-NO2) as the most effective radical scavengers. The most active compounds were also evaluated for drug-likeness using in silico Lipinski’s rule assessments. Conclusions: The synthesized 3,19-(N-phenyl-3-aryl-pyrazole) acetals of andrographolide and isoandrographolide exhibited promising anticancer and antioxidant properties. Among them, compound 1f showed the most significant activity, supporting its potential as a lead candidate for further anticancer drug development.
Related Topics
Concepts
Andrographolide
Andrographis paniculata
Pyrazole
Lipinski's rule of five
Apoptosis
Chemistry
Cell cycle checkpoint
Pharmacophore
Cancer cell
Cell cycle
MTT assay
Pharmacology
Cancer
Stereochemistry
In silico
Biochemistry
Medicine
Alternative medicine
Pathology
Gene
Internal medicine
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3390/ph18071026
- https://www.mdpi.com/1424-8247/18/7/1026/pdf?version=1752148174
- OA Status
- gold
- References
- 61
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4412162261
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4412162261Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.3390/ph18071026Digital Object Identifier
- Title
-
Novel 3,19-(N-Phenyl-3-(4-fluorophenyl)-pyrazole) Acetal of Andrographolide Promotes Cell Cycle Arrest and Apoptosis in MDA-MB-231 Breast Cancer CellsWork title
- Type
-
articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2025Year of publication
- Publication date
-
2025-07-10Full publication date if available
- Authors
-
Siva Kumar Rokkam, Shahjalal Chowdhury, Yashwanth Inabathina, Lakshminath Sripada, Srinivas Nanduri, Balasubramanyam Karanam, Nageswara Rao GolakotiList of authors in order
- Landing page
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https://doi.org/10.3390/ph18071026Publisher landing page
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https://www.mdpi.com/1424-8247/18/7/1026/pdf?version=1752148174Direct link to full text PDF
- Open access
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YesWhether a free full text is available
- OA status
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goldOpen access status per OpenAlex
- OA URL
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https://www.mdpi.com/1424-8247/18/7/1026/pdf?version=1752148174Direct OA link when available
- Concepts
-
Andrographolide, Andrographis paniculata, Pyrazole, Lipinski's rule of five, Apoptosis, Chemistry, Cell cycle checkpoint, Pharmacophore, Cancer cell, Cell cycle, MTT assay, Pharmacology, Cancer, Stereochemistry, In silico, Biochemistry, Medicine, Alternative medicine, Pathology, Gene, Internal medicineTop concepts (fields/topics) attached by OpenAlex
- Cited by
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0Total citation count in OpenAlex
- References (count)
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61Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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