Abstract
Background: Resveratrol (RV) and its analogues Aza-stilbenes were found effective in exhibiting anticancer activity.
Objective: The present study mainly focused on the green synthesis of novel imine stilbene analogues and evaluation of their anticancer activity besides their influence on hypoxia-induced gene expression in cancer cells.
Method: Novel imine stilbenes, differing in number and/or position of hydroxyl and methoxy functional groups, have been synthesized using green chemistry mediated condensation reaction between aldehydes and amines in the ethanolic extract of Psoralea corylifolia hairy roots and tested for their anticancer potential.
Results: Ethanol containing 1% hairy root extract facilitated instant reaction and yielded more than 99% product( s). MTT assay on HeLa cells treated with imine stilbene analogues revealed an increase in the inhibition of cell proliferation as compared to RV. Treatment of nontumor HEK293 cells with these compounds disclosed minimal toxicity implying the selective advantage of these compounds for cervical cancer therapy. Scratch assay on HeLa cells displayed inhibition of directional cell motility by these analogues and compound 3e [4-((E)-(4- hydroxyphenylimino)methyl)-2-methoxyphenol] recorded maximum inhibition. In reporter assay, as compared to untreated N-(2-Methoxy-2-oxoacetyl) glycine methyl ester (DMOG) induced cells, hypoxia response element- directed transcriptional activity has been significantly reduced in DMOG induced cells treated with imine stilbene analogues.
Conclusion: Overall results indicated that four of the five imine stilbene analogues exhibited enhanced anticancer activity than that of the RV. As such, the novel synthetic compounds 3d, 3e and 3b endowed with potent anticancer activity than RV can serve as drug lead molecules.
Keywords: Imine stilbenes, anti-cancer activity, cell survival, cell motility, HIF-1α, analogs.
Anti-Cancer Agents in Medicinal Chemistry
Title:Synthesis of Novel Imine Stilbene Analogs Exhibiting Potent Anticancer Activity
Volume: 17 Issue: 11
Author(s): Raju Naini, Eslavath Ravikumar, Surya S. Singh, Rama K. Kancha, Khareedu V. Rao and Vudem D. Reddy*
Affiliation:
- CPMB, Osmania University, Hyderabad, 500007,India
Keywords: Imine stilbenes, anti-cancer activity, cell survival, cell motility, HIF-1α, analogs.
Abstract: Background: Resveratrol (RV) and its analogues Aza-stilbenes were found effective in exhibiting anticancer activity.
Objective: The present study mainly focused on the green synthesis of novel imine stilbene analogues and evaluation of their anticancer activity besides their influence on hypoxia-induced gene expression in cancer cells.
Method: Novel imine stilbenes, differing in number and/or position of hydroxyl and methoxy functional groups, have been synthesized using green chemistry mediated condensation reaction between aldehydes and amines in the ethanolic extract of Psoralea corylifolia hairy roots and tested for their anticancer potential.
Results: Ethanol containing 1% hairy root extract facilitated instant reaction and yielded more than 99% product( s). MTT assay on HeLa cells treated with imine stilbene analogues revealed an increase in the inhibition of cell proliferation as compared to RV. Treatment of nontumor HEK293 cells with these compounds disclosed minimal toxicity implying the selective advantage of these compounds for cervical cancer therapy. Scratch assay on HeLa cells displayed inhibition of directional cell motility by these analogues and compound 3e [4-((E)-(4- hydroxyphenylimino)methyl)-2-methoxyphenol] recorded maximum inhibition. In reporter assay, as compared to untreated N-(2-Methoxy-2-oxoacetyl) glycine methyl ester (DMOG) induced cells, hypoxia response element- directed transcriptional activity has been significantly reduced in DMOG induced cells treated with imine stilbene analogues.
Conclusion: Overall results indicated that four of the five imine stilbene analogues exhibited enhanced anticancer activity than that of the RV. As such, the novel synthetic compounds 3d, 3e and 3b endowed with potent anticancer activity than RV can serve as drug lead molecules.
Export Options
About this article
Cite this article as:
Naini Raju , Ravikumar Eslavath , Singh S. Surya , Kancha K. Rama , Rao V. Khareedu and Reddy D. Vudem *, Synthesis of Novel Imine Stilbene Analogs Exhibiting Potent Anticancer Activity, Anti-Cancer Agents in Medicinal Chemistry 2017; 17 (11) . https://dx.doi.org/10.2174/1871520617666170327122929
DOI https://dx.doi.org/10.2174/1871520617666170327122929 |
Print ISSN 1871-5206 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5992 |
Call for Papers in Thematic Issues
Discovery of Lead compounds targeting transcriptional regulation
Transcriptional regulation plays key physiological functions in body growth and development. Transcriptional dysregulation is one of important biomarkers of tumor genesis and progression, which is involved in regulating tumor cell processes such as cell proliferation, differentiation, and apoptosis. Additionally, it plays a pivotal role in angiogenesis and promotes tumor metastasis ...read more
Induction of cell death in cancer cells by modulating telomerase activity using small molecule drugs
Telomeres are distinctive but short stretches present at the corners of chromosomes and aid in stabilizing chromosomal makeup. Resynthesis of telomeres supported by the activity of reverse transcriptase ribonucleoprotein complex telomerase. There is no any telomerase activity in human somatic cells, but the stem cells and germ cells undergone telomerase ...read more
Innovative targets in medicinal chemistry
Medicinal chemistry continuously evolves in response to emerging healthcare needs and advancements in scientific understanding. This special issue explores the current landscape of innovative targets in medicinal chemistry, highlighting the quest for novel therapeutic avenues. From traditional drug targets such as enzymes and receptors to emerging targets like protein-protein interactions ...read more
Rechallenge Therapy in different types of cancer
Cancer is responsible for approximately 8 million deaths annually all worldwide. The Global burden of cancer (GLOBOCAN) 2020 reported 19.3 million new cases of cancer, which is projected to increase to 28.4 million by 2040.In the future , female breast cancer will be the most common cancer (11.7%) followed by ...read more
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Insights into the Role of mTOR/AMPK as a Potential Target for Anticancer Therapy
Current Drug Therapy Cancer Stem Cells: The ‘Achilles Heel’ of Chemo-Resistant Tumors
Recent Patents on Anti-Cancer Drug Discovery Evaluation of Anticancer, Antibacterial and Antioxidant Properties of a Medicinally Treasured Fern Tectaria coadunata with its Phytoconstituents Analysis by HR-LCMS
Anti-Cancer Agents in Medicinal Chemistry Secretory Leukocyte Protease Inhibitor: More than Just A Protease Inhibitor
Current Immunology Reviews (Discontinued) Triterpenoids for Cancer Prevention and Treatment: Current Status and Future Prospects
Current Pharmaceutical Biotechnology Design of Curcumin loaded Cellulose Nanoparticles for Prostate Cancer
Current Drug Metabolism Gap Junctions as Targets for Cancer Chemoprevention and Chemotherapy
Current Drug Targets Development of a High Throughput Drug Screening Assay for the Detection of Changes in Tau Levels - Proof of Concept with HSP90 inhibitors
Current Alzheimer Research Hsp90 Flexibility and Development of its Inhibitors for the Treatment of Cancer
Current Chemical Biology Positron Emission Tomography Imaging of Tumor Hypoxia
Current Medical Imaging Experimental and Computational Insights into Bis-indolylmethane Derivatives as Potent Antimicrobial Agents Inhibiting 2,2-dialkylglycine Decarboxylase
Current Enzyme Inhibition Cell Cycle Regulatory Protein 5 (Cdk5) is a Novel Downstream Target of ERK in Carboplatin Induced Death of Breast Cancer Cells (Supplementary Data)
Current Cancer Drug Targets Type Specific Human Papilloma Virus Prevalence and Distribution in Women with Abnormal Cervical Cytology: A Single Centre Retrospective Observational Study in the Emirate of Abu Dhabi
New Emirates Medical Journal Cancer Proteomics: New Horizons and Insights into Therapeutic Applications
Current Proteomics Sugar-Borate Esters – Potential Chemical Agents in Prostate Cancer Chemoprevention
Anti-Cancer Agents in Medicinal Chemistry Shutting Down the Furnace: Preferential Killing of Cancer Cells with Mitochondrial-Targeting Molecules
Current Medicinal Chemistry Chitosan and Quercetin: Potential Hand in Hand Encountering Tumors in Oral Delivery System
Current Pharmaceutical Design Notch Signaling: A Potential Therapeutic Target in Prostate Cancer
Current Cancer Drug Targets Emerging Electrical Biosensors for Detecting Pathogens and Antimicrobial Susceptibility Tests
Current Organic Chemistry Biologically Active Phytochemicals: A Brief Appraisal
Current Traditional Medicine