ArticleCancer cell international2017
Anticancer properties of ester derivatives of betulin in human metastatic melanoma cells (Me-45).
Article in Cancer cell international, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 57 citations in OpenAlex.
- Plant-Derived Compounds as Potential Sensitizers to Immunotherapy in Melanoma.International journal of molecular sciences · 2026Review
- Betulin-Amino Acid Molecular Hybrids: Synthesis, Structure and Pharmacological Potential.International journal of molecular sciences · 2026Article
- Thermodynamic stability and anticancer activity of 2,3-unsaturated and 2,3-dideoxy OScientific reports · 2026Article
- Anoikis: To Die or Not to Die?International journal of molecular sciences · 2026Review
- Uncovering New Antimelanoma Strategies: Experimental Insights into Semisynthetic Pentacyclic Triterpenoids.Life (Basel, Switzerland) · 2025Article
- Promising Protocol for In Vivo Experiments with Betulin.Pharmaceutics · 2025Article
- Chemopreventive and Chemotherapeutic Potential of Betulin and Betulinic Acid: Mechanistic Insights From In Vitro, In Vivo and Clinical Studies.Food science & nutrition · 2024Review
- Complex Inhibitory Activity of Pentacyclic Triterpenoids against Cutaneous Melanoma In Vitro and In Vivo: A Literature Review and Reconstruction of Their Melanoma-Related Protein Interactome.ACS pharmacology & translational science · 2024Review
- Innovative Approach to Enhance Bioavailability of Birch Bark Extracts: Novel Method of Oleogel Development Contrasted with Other Dispersed Systems.Plants (Basel, Switzerland) · 2024Article
- New benzothiazole hybrids as potential VEGFR-2 inhibitors: design, synthesis, anticancer evaluation, andJournal of enzyme inhibition and medicinal chemistry · 2023Article
- Progress in Antimelanoma Research of Natural Triterpenoids and Their Derivatives: Mechanisms of Action, Bioavailability Enhancement and Structure Modifications.Molecules (Basel, Switzerland) · 2023Review
- The Influence of Long Carbon Chains on the Antioxidant and Anticancer Properties ofPharmaceuticals (Basel, Switzerland) · 2023Article
- An Integrated Molecular Networking and Docking Approach to Characterize the Metabolome ofMetabolites · 2023Article
- Betulin and Its Derivatives Reduce Inflammation and COX-2 Activity in Macrophages.Inflammation · 2023Article
- Chaga mushroom triterpenoids as adjuncts to minimally invasive cancer therapies: A review.Current research in toxicology · 2023Article
- Novel Triterpenic Acid-Benzotriazole Esters Act as Pro-Apoptotic Antimelanoma Agents.International journal of molecular sciences · 2022Article
- Design, Synthesis and Preliminary Evaluation of the Cytotoxicity and Antibacterial Activity of Novel Triphenylphosphonium Derivatives of Betulin.Molecules (Basel, Switzerland) · 2022Article
- Drug Candidates for Autoimmune Diseases.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Synthesis, Structural Characterization and Anticancer Activity of New 5-Trifluoromethyl-2-thioxo-thiazolo[4,5-Pharmaceuticals (Basel, Switzerland) · 2022Article
- Anti-Inflammatory and Anticancer Properties of Birch Bark-Derived Betulin: Recent Developments.Plants (Basel, Switzerland) · 2021Review
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
backgroundBetulinic acid and betulin are triterpenes that have anticancer properties in various types of cancer. Unfortunately, the bioavailability and the bio-distribution of betulinic acid and its metabolic precursor, betulin are very low because of poor solubility in aqueous buffers.
methodsIn this study, we examined the anticancer properties of the ester derivatives of betulin compared to their precursors in a malignant melanoma cell line. We assessed five amino acid esters of betulin. The compounds contained four basic amino acids-natural lysine (l-Lys-OH) and three of its derivatives (l-Dap-OH, l-Dab-OH, and l-Orn-OH)-and alanine (l-Ala-OH) as a negative control (amino acid without an amine group in the side chain). The derivatives were more soluble than their precursors (betulin and betulinic acid) in water. The betulin esters were tested in the malignant melanoma cell line Me-45. To evaluate the cytotoxicity, MTT test was performed after 24, 48 and 72 h of incubation with the test compounds at a concentration range of 0.75-100 μM. For analysis of the apoptotic activity, TUNEL assay was performed. Additionally, expression of caspase-3 and PARP-1 was investigated immunocytochemically.
resultsThe highest biological activity was observed with the lysine ester. The results showed that the highest cytotoxicity and the highest number of positively stained nuclei in metastatic melanoma Me-45 cells were obtained after 72 h of incubation with betulin derivatives containing lysine and ornithine.
conclusionsThe betulin ester derivatives showed enhanced antitumor activity compared to their non-modified precursors. Esters of betulin can be more potent anticancer agents than their precursor as a consequence of the rapid bioavailability and increased concentration in cancer cells.
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