Abstract
The ability of garlic preparations to inhibit cancer cell-growth has been attributed to a group of structurally-related organosulfur compounds found in the crushed clove. Historically, interest has centred on three such compounds as allicin, diallyl disulfide and diallyl trisulfide, with less interest on E- and Z-ajoene. A recently developed synthetic route from our laboratory for preparing ajoene analogues allows access to derivatives containing the sulfoxide / vinyl disulfide core whilst varying the terminal end-group functionality. A small library has been synthesized and an advanced lead with p-methoxybenzyl end groups (8) identified. Data on the in vitro anti-proliferation activity of compound (8) is presented here on six cancer cell-lines in comparison with that of Z- and E-ajoene to reveal an enhancement in activity of up to twelvefold. In addition, a modest selectivity is observed for tumour over normal cell-lines of up to threefold. Data on ajoene and its derivatives is presented in the context of chemosensitization in drug-resistance, and ideas on ajoenes mode of action at the molecular level are presented and discussed.
Keywords: Garlic, Ajoene, Anti-Cancer, Ajoene Analogues, Disulfide, sulfenyl substituent, E- and Z-isomeric forms, E/Z-mixtures, tumorogenic lymphoid cells (BJA-B), proliferation, fibroblasts, para-methoxybenzyl groups, peripheral mononuclear, blood cells, Anti-Cancer Drug
Anti-Cancer Agents in Medicinal Chemistry
Title: Anti-Proliferative Activity of Synthetic Ajoene Analogues on Cancer Cell-Lines
Volume: 11 Issue: 3
Author(s): Catherine H. Kaschula, Roger Hunter, Hassan T. Hassan, Nashia Stellenboom, Jonathan Cotton, Xiao Q. Zhai and M. Iqbal Parker
Affiliation:
Keywords: Garlic, Ajoene, Anti-Cancer, Ajoene Analogues, Disulfide, sulfenyl substituent, E- and Z-isomeric forms, E/Z-mixtures, tumorogenic lymphoid cells (BJA-B), proliferation, fibroblasts, para-methoxybenzyl groups, peripheral mononuclear, blood cells, Anti-Cancer Drug
Abstract: The ability of garlic preparations to inhibit cancer cell-growth has been attributed to a group of structurally-related organosulfur compounds found in the crushed clove. Historically, interest has centred on three such compounds as allicin, diallyl disulfide and diallyl trisulfide, with less interest on E- and Z-ajoene. A recently developed synthetic route from our laboratory for preparing ajoene analogues allows access to derivatives containing the sulfoxide / vinyl disulfide core whilst varying the terminal end-group functionality. A small library has been synthesized and an advanced lead with p-methoxybenzyl end groups (8) identified. Data on the in vitro anti-proliferation activity of compound (8) is presented here on six cancer cell-lines in comparison with that of Z- and E-ajoene to reveal an enhancement in activity of up to twelvefold. In addition, a modest selectivity is observed for tumour over normal cell-lines of up to threefold. Data on ajoene and its derivatives is presented in the context of chemosensitization in drug-resistance, and ideas on ajoenes mode of action at the molecular level are presented and discussed.
Export Options
About this article
Cite this article as:
H. Kaschula Catherine, Hunter Roger, T. Hassan Hassan, Stellenboom Nashia, Cotton Jonathan, Q. Zhai Xiao and Iqbal Parker M., Anti-Proliferative Activity of Synthetic Ajoene Analogues on Cancer Cell-Lines, Anti-Cancer Agents in Medicinal Chemistry 2011; 11 (3) . https://dx.doi.org/10.2174/187152011795347450
DOI https://dx.doi.org/10.2174/187152011795347450 |
Print ISSN 1871-5206 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5992 |
Call for Papers in Thematic Issues
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
Role of natural compounds as anti anti-cancer agents
Cancer is considered the leading cause of worldwide mortality, accounting for nearly 10 million deaths in 2022. Cancer outcome can be improved through an appropriate screening and early detection and through an efficient clinical treatment. Chemotherapy remains an important approach in treatment o f several types of cancers, even though ...read more
Signaling and enzymatic modulators in cancer treatment
Cancer accounts for nearly 10 million deaths in 2022 and is considered the leading cause of worldwide mortality. Cancer outcome can be improved through an appropriate screening and early detection and through an efficient clinical treatment. Chemotherapy, radiotherapy and surgery are the most important approach for the treatment of several ...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
-
Resveratrol and Analogues: A Review of Antioxidant Activity and Applications to Human Health
Recent Patents on Food, Nutrition & Agriculture Reactive Oxygen Species, Inflammation, and Lung Diseases
Current Pharmaceutical Design The Anti-Inflammatory and Pharmacological Actions of Oleocanthal, a Phenolic Contained in Extra Virgin Olive Oil
Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry Targeting MDM4 as a Novel Therapeutic Approach for Hematologic Malignancies
Current Cancer Drug Targets Role of Polyamines in Breast Cancer Growth, Development and Progression
Current Cancer Therapy Reviews Estrogen Receptor Signaling: Impact on Cell Functions
Current Signal Transduction Therapy Exploring Promises of siRNA in Cancer Therapeutics
Current Cancer Therapy Reviews Endogenous Events Modulating Myogenic Regulation of Cerebrovascular Function
Current Vascular Pharmacology Risk Factors for Serious Adverse Effects of Thiopurines in Patients with Crohn’s Disease
Current Drug Safety Molecular Mistletoe Therapy: Friend or Foe in Established Anti-Tumor Protocols? A Multicenter, Controlled, Retrospective Pharmaco-Epidemiological Study in Pancreas Cancer
Current Molecular Medicine Systems Medicine Approaches to Improving Understanding, Treatment, and Clinical Management of Neuroendocrine Prostate Cancer
Current Pharmaceutical Design Molecular Remodeling of the Insulin Receptor Pathway by Thiazolidinediones in Type 2 Diabetes Mellitus: A Brief Review
Protein & Peptide Letters Role of Tyrosine Phosphatase Inhibitors in Cancer Treatment with Emphasis on SH2 Domain-Containing Tyrosine Phosphatases (SHPs)
Anti-Cancer Agents in Medicinal Chemistry Strategies for Increasing the Solubility and Bioavailability of Anticancer Compounds: β-Lapachone and Other Naphthoquinones
Current Pharmaceutical Design Selective Neuronal Nitric Oxide Synthase Inhibitors
Current Topics in Medicinal Chemistry In Vitro Investigation Demonstrates IGFR/VEGFR Receptor Cross Talk and Potential of Combined Inhibition in Pediatric Central Nervous System Atypical Teratoid Rhabdoid Tumors
Current Cancer Drug Targets Eosinophilic Gastrointestinal Diseases in Children: A Practical Review
Current Pediatric Reviews miRNA Targeting Angiogenesis as a Potential Therapeutic Approach in the Treatment of Colorectal Cancers
Current Pharmaceutical Design TWIST1 Gene: First Insights in Felis catus
Current Genomics Current Immune Therapies of Autoimmune Disease of the Nervous System with Special Emphasis to Multiple Sclerosis
Current Pharmaceutical Design