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| Targets |
Histone deacetylases (HDACs). Oxamflatin is a potent HDAC inhibitor with an IC50 of 15.7 nM. HDACs are enzymes that remove acetyl groups from histone proteins, leading to chromatin condensation and transcriptional repression. By inhibiting HDACs, Oxamflatin increases histone acetylation, which promotes a more open chromatin structure and activates the transcription of genes involved in cell cycle arrest, differentiation, and apoptosis. Oxamflatin is a selective HDAC inhibitor. The compound's alkyne group allows it to be used in click chemistry reactions, making it a useful tool for studying HDAC biology and for developing HDAC-targeted therapies.
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| ln Vitro |
Various NIH3T3-derived transformed cell lines exhibit morphological reversal and junD transcriptional activation upon exposure to oxamflatin. When applied to several tumor cell lines from mice and humans, oxamflatin has antiproliferative activity and significantly alters the shape of the cells. HeLa cells that are exposed to olefantine undergo morphological elongation and filamentous protrusions, as well as a G1 phase cell cycle arrest. In a dose-dependent manner, oxamflatin significantly increases the transcriptional activity of the CMV promoter and suppresses intracellular HDAC activity [1]. OVCAR-5 and SKOV-3 ovarian cancer cell lines undergo morphological alterations when exposed to oxamflatin at nanomolar concentrations. Additionally, oxaxanthin treatment reduced the vitality of the cells. Cell division and DNA synthesis can be strongly inhibited by oxamflatin [2]. In the MKN-45 cell line, oxamflatin can decrease cell viability and promote the expression of E-cadherin [3].
Oxamflatin is a potent HDAC inhibitor with an IC50 of 15.7 nM. The compound induces an elongated cell shape morphology with filamentous protrusions. It shows antiproliferative effects in various cancer cell lines. Oxamflatin increases histone acetylation by inhibiting HDAC activity, thereby regulating gene expression, cell cycle, and apoptosis. The compound's alkyne group allows it to be used in click chemistry reactions for labeling and detection applications. Oxamflatin is a potent mammalian HDAC inhibitor. |
| ln Vivo |
Oxapine injections six times at a dose of 20 mg/kg resulted in a considerable increase in survival days (38 percent of ILS). One mouse lived for more than 60 days following tumor inoculation, while mice given oxamamine at a dose of 50 mg/kg were found to have an ILS of more than 67%. There were no negative consequences, such as weight loss, at least not at this dosage [1].
Oxamflatin has been studied in vivo for its antitumor effects. The compound shows antitumor effects in vivo. By inhibiting HDACs, Oxamflatin modulates gene expression, cell cycle, and apoptosis, leading to reduced tumor growth. Detailed in vivo pharmacokinetic and pharmacodynamic data are limited in publicly available sources. Oxamflatin is for research use only and is not for human therapeutic use. |
| Enzyme Assay |
HDAC enzyme inhibition assays are performed using recombinant HDAC enzymes (e.g., HDAC1, HDAC2, HDAC3, HDAC6) or nuclear extracts from cancer cells. The enzyme is incubated with a fluorogenic substrate (e.g., acetylated lysine-AMC) in assay buffer. Deacetylation allows cleavage of the AMC group by trypsin, generating a fluorescent signal measured at excitation 360 nm, emission 460 nm. Oxamflatin is serially diluted in DMSO and added to the reaction mixture. The IC50 for HDAC inhibition is 15.7 nM. Each concentration is tested in duplicate, and IC50 values are calculated by non-linear regression analysis. Appropriate positive controls (e.g., SAHA, TSA) and vehicle controls are included to validate the assay.
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| Cell Assay |
Cellular HDAC inhibition is evaluated in cancer cell lines. Cells are cultured in appropriate media at 37°C with 5% CO₂ and treated with Oxamflatin at concentrations ranging from 1 nM to 10 μM for 24-72 hours. Histone acetylation is measured by Western blotting using anti-acetyl-H3 and anti-acetyl-H4 antibodies. Cell viability and proliferation are assessed using MTT or CellTiter-Glo assays. Cell morphology is assessed by microscopy to observe elongated cell shape with filamentous protrusions. Apoptosis is evaluated by Annexin V/PI staining and caspase-3/7 activity assays. Each experiment includes vehicle controls and appropriate positive controls (e.g., SAHA, TSA) to validate the assay systems.
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| Animal Protocol |
In vivo efficacy of Oxamflatin is evaluated in mouse xenograft models using human cancer cell lines. Tumor cells are implanted subcutaneously in immunodeficient mice. When tumors reach a predetermined size, mice are randomized into treatment and control groups. Oxamflatin is administered orally or intraperitoneally at doses determined by preclinical studies. Tumor growth is monitored by caliper measurements. At study endpoint, tumors are harvested for histopathological analysis, immunohistochemistry (Ki67 for proliferation, cleaved caspase-3 for apoptosis), and biochemical assays (histone acetylation). Body weight and clinical signs are monitored throughout the study to assess tolerability. Sample sizes typically range from 6-10 animals per group.
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| ADME/Pharmacokinetics |
Molecular Weight: 342.37. Formula: C17H14N2O4S. CAS No.: 151720-43-3. Synonyms: Metacept-3. Appearance: Solid. Purity: >95%. Solubility: DMSO. Storage: Typically at -20°C. Oxamflatin is a potent HDAC inhibitor with an IC50 of 15.7 nM. It is a click chemistry reagent containing an alkyne group.
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| Toxicity/Toxicokinetics |
No comprehensive toxicology data are publicly available for Oxamflatin. The compound is intended for research use only and has not undergone full preclinical toxicology evaluation required for clinical development. As an HDAC inhibitor, potential toxicities may include effects on normal tissues, particularly rapidly dividing cells. Standard toxicity studies would include acute toxicity assessment in rodents, repeated dose toxicity studies (14-day and 28-day), and genotoxicity screening (Ames test, micronucleus assay). The compound is for research use only and not for human therapeutic use.
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| References |
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| Additional Infomation |
5-[3-(benzenesulfonamido)phenyl]-N-hydroxypent-2-ene-4-yneamide is a sulfonamide. Osamfatin is a histone deacetylase inhibitor. It is an aromatic sulfonamide hydroxamic acid ester, initially discovered during screening for inhibitors of tumorigenic phenotypes in K-ras-transformed NIH3T3 cells.
Oxamflatin is also known as Metacept-3. Its IUPAC name is not fully resolved in publicly available sources. Oxamflatin is a potent HDAC inhibitor with an IC50 of 15.7 nM. It induces an elongated cell shape morphology with filamentous protrusions and shows antiproliferative and antitumor effects. Oxamflatin contains an alkyne group for click chemistry applications. No clinical trials have been reported for this compound. Oxamflatin is for research use only. |
| Molecular Formula |
C17H14N2O4S
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| Molecular Weight |
342.36906
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| Exact Mass |
342.067
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| CAS # |
151720-43-3
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| PubChem CID |
5353852
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Index of Refraction |
1.686
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| LogP |
3.26
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
24
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| Complexity |
618
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC(=C2)C#C/C=C/C(=O)NO
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| InChi Key |
QRPSQQUYPMFERG-LFYBBSHMSA-N
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| InChi Code |
InChI=1S/C17H14N2O4S/c20-17(18-21)12-5-4-7-14-8-6-9-15(13-14)19-24(22,23)16-10-2-1-3-11-16/h1-3,5-6,8-13,19,21H,(H,18,20)/b12-5+
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| Chemical Name |
(E)-5-[3-(benzenesulfonamido)phenyl]-N-hydroxypent-2-en-4-ynamide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~146.04 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 2.08 mg/mL (6.08 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. View More
Solubility in Formulation 3: 2.08 mg/mL (6.08 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9208 mL | 14.6041 mL | 29.2082 mL | |
| 5 mM | 0.5842 mL | 2.9208 mL | 5.8416 mL | |
| 10 mM | 0.2921 mL | 1.4604 mL | 2.9208 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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