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Product name: 3-O-Acetylbufotalin
Synonym name: Bufotalin 3-acetate
Catalogue No.: BP2069
Cas No.: 4029-69-0
Formula: C28H38O7
Mol Weight: 486.605
Botanical Source: Bufonis Venenum
Type of Compound: Steroids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
HPLC of 3-O-Acetylbufotalin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
103.0400
3.3764
3.3761
.0096
3.7193
3.8990
High
87.2124
4.6442
No
No
No
No
Yes
No
0.0
No
No
No
Yes
3-Acetylbufotalin is an important natural product of the toxadienic acid lactone group, which has attracted widespread attention in recent years due to its remarkable biological activity, especially its anticancer potential. As one of the active components in toad secretions, 3-acetyltoxin Taling not only demonstrates multi-target regulatory capabilities but also shows potential value in the treatment of cardiovascular diseases such as heart failure. This paper will systematically review the chemical structure, physicochemical properties, sources, and extraction methods of 3-acetyltoxin Taling, delve into its pharmacological activity and mechanism of action, evaluate its druggability and pharmacokinetic characteristics, and look ahead to its clinical application prospects.
3-Acetyltoxin Tarin belongs to the tonophenyl hydroxylactone class of tonophenyl hydroxylate, with a molecular formula of C_28H_42O_7 and a molecular weight of 486.6050. The compound structure contains a typical steroid backbone, supplemented by acetylated hydroxyl modifications, giving it its unique chemical properties. Its LogP value is 3.3764, indicating moderate lipid solubility, which facilitates cell membrane penetration. The topological pole surface area (TPSA) is 103.0400, indicating certain polarity that helps bind with biological macromolecules. Low water solubility (0.0096 mg/mL) suggests that it may require appropriate carriers or solvent systems in vivo to improve bioavailability. High blood-brain barrier permeability indicates that this compound has potential central nervous system activity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames-induced mutagenic test was 0.0, indicating a low genotoxicity risk for this compound.
3-Acetyltotoxin Taling mainly originates from toad skin secretions, especially species such as the Chinese toad (Bufo gargarizans) and the black-spotted toad (Bufo melanostictus). Toad secretions are rich in various toxin steroids, and 3-acetyltoxin tatoxin, as one of its derivatives, has high levels and biological activity.
The extraction process typically uses solvent extraction combined with column chromatography separation technology. The specific steps include: first, use ethanol or methanol to extract the toad skin secretions to extract the crude extract containing toadsin; Further purification is then performed by silica gel column chromatography or high-performance liquid chromatography (HPLC), utilizing polarity differences to separate the target compounds. In recent years, ultrasound-assisted extraction and supercritical CO_2 extraction technologies have also been applied to improve extraction efficiency and purity. In addition, identification methods mainly rely on modern analytical techniques such as mass spectrometry (MS), nuclear magnetic resonance imaging (NMR), and infrared spectroscopy (IR) to ensure the structural accuracy and purity of the extracts.
Pharmacological studies on the pharmacological activity of 3-acetyltoxin taling mainly focus on its anticancer and cardiovascular protective effects.
Numerous in vitro cell experiments have shown that 3-acetyltoxin has a significant inhibitory effect on various cancer cell lines, including but not limited to lung cancer, breast cancer, liver cancer, and gastric cancer cells. Its anti-cancer mechanism involves inducing apoptosis, inhibiting cell proliferation, blocking the cell cycle, and suppressing tumor cell migration and invasion. In vivo tumor model studies have also confirmed that it can significantly slow tumor growth and reduce tumor burden. Additionally, 3-acetyltoxin tarin exhibits low systemic toxicity within a certain dose range, demonstrating good safety.
In recent years, the potential therapeutic value of 3-acetyltoxin tatoxin in cardiovascular diseases such as heart failure has gradually been revealed. By modulating multiple key targets such as AMPK (PRKAA1), EHMT2, APP, PTPN1, MAOA, ESR2, ABCB1, ALOX15, ABCG2, and FEN1, it participates in myocardial energy metabolism, oxidative stress response, inflammation regulation, and apoptosis, thereby improving myocardial function and reducing pathological progression of heart failure.
The mechanism of action of 3-Acetyltoxin Taling is complex and involves multi-target synergistic regulation, mainly involving the following aspects:
AMPK (5' AMP-activated protein kinase), as a key regulator of cellular energy metabolism, has its activity regulation crucial for the energy balance of cardiomyocytes. 3-Acetyltoxin Taling can activate AMPK, promote fatty acid oxidation and glucose metabolism, reduce myocardial energy metabolism disorders, and improve heart failure.
EHMT2 (histone methyltransferase G9a) is an important epigenetic regulator involved in gene expression inhibition. 3-Acetyltoxin Taling exerts a protective effect on the myocardium by regulating EHMT2 activity, affecting the expression of genes related to cardiomyocyte proliferation and apoptosis.
MAOA (monoamine oxidase A) participates in neurotransmitter metabolism and regulates autonomic nervous system function in the heart. 3-Acetyltoxin Taling regulates MAOA and helps improve cardiac nerve imbalances and alleviate heart failure symptoms.
ABCB1 and ABCG2 are important drug efflux pumps, affecting drug absorption, distribution, and excretion. The regulation of these two transport proteins by 3-acetyltoxin Taling may affect the pharmacokinetic characteristics of the drug itself and other drugs, suggesting potential interactions in combination therapy.
FEN1 (nucleose 1) is involved in DNA repair and replication. 3-Acetyltoxin Taling regulates FEN1, affects tumor cells' ability to repair DNA damage, enhances cell apoptosis, and thus exerts anti-cancer effects.
In summary, 3-Acetyltoxin Taling regulates cardiovascular and tumor-related pathological processes through multi-target and multi-pathway synergistic effects, demonstrating its complex and effective pharmacological mechanism.
The druggability evaluation of 3-acetyltoxin tarin shows that it has good development potential. Its molecular weight (486.6) and LogP (3.38) both met the Lipinski rule, indicating good oral bioavailability. TPSA is 103.04, indicating moderate polarity, which is favorable for target binding.
Low water solubility is a major challenge in formulation development, requiring improved solubility and bioavailability through technologies such as nanocarriers, liposomes, or solid dispersions. Its high blood-brain barrier permeability offers potential for treating central nervous system diseases, but potential CNS toxicity is also noteworthy.
In terms of safety, the hERG channel inhibition test was negative, reducing the risk of arrhythmias; The Ames test showed no mutagenicity and showed a low risk of genotoxicity.
Pharmacokinetic studies show that 3-acetyltoxin Taling is widely distributed in the body, especially enriched in heart and liver tissues, aligning with its pharmacological target. Its metabolism mainly occurs through the hepatic cytochrome P450 enzyme system, and the activity and toxicity of these metabolites require further research. Moderate half-life, supporting routine dosing regimen design.
Due to its significant anticancer activity and cardiovascular protective effects, 3-acetyltoxin thaling has broad prospects for clinical translation. In the field of anti-cancer treatments, especially for refractory tumors, the potential of 3-acetyltoxin thalin as a candidate or combination therapy is worth further exploration. In heart failure treatment, it regulates myocardial energy metabolism and cellular function through multiple targets, potentially becoming an important supplement to new therapeutic strategies.
Future research should focus on:
Systematic evaluation of pharmacokinetics and safety: including in-depth research on long-term toxicology, metabolite activity, and potential drug interactions.
Dosage form optimization and drug delivery route exploration: Improving water solubility and bioavailability to develop formulations suitable for clinical applications.
Preclinical and clinical trial design: Define effective dose ranges and evaluate efficacy and safety in patients with cancer and cardiovascular diseases.
Molecular-level analysis of the mechanism of action: Using multi-omics techniques, further revealing its multi-target network of action to guide the design of precision therapy plans.
Combination therapy strategy research: Exploring synergistic effects with existing anticancer drugs and heart failure treatment drugs to enhance treatment outcomes.
3-Acetyltoxin, as a natural product of the toxadiene hydroxylactone group, demonstrates great potential in cancer and cardiovascular disease treatment due to its unique chemical structure and multi-target pharmacological activity. Its excellent druggability parameters and safety evaluation lay the foundation for clinical translation. In the future, through in-depth mechanistic research, pharmacokinetic optimization, and clinical validation, 3-acetyltoxin Taling is expected to become an important representative of natural product drug development, providing new ideas and methods for the treatment of related diseases.
Shenshuai
Wenjing
Hedandan
