| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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| Other Sizes |
Purity: ≥98%
| Targets |
Hadacidin primarily targets adenylosuccinate synthetase (AdSS), a key enzyme in the purine nucleotide biosynthesis pathway. It also targets purine nucleoside phosphorylase (PNP). By binding to the active site of adenylate synthase, it competitively inhibits the binding of the natural substrate L-aspartate. This action prevents the conversion of inosine monophosphate (IMP) to adenylosuccinate, a critical step in the de novo synthesis of adenine nucleotides.
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| ln Vitro |
In vitro, hadacidin effectively inhibits adenylate synthase activity by competitively blocking L-aspartate binding. It has significant inhibitory effects on various human cancer cell lines, including human adenocarcinoma (HAD# 1), human epithelial carcinoma-3, and bronchial carcinoma-A42. The compound also inhibits adenosine and deoxyadenosine biosynthesis. Hadacidin and its analogs have demonstrated activity against adenylosuccinate synthetase and exhibit anticancer properties.
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| ln Vivo |
In vivo, hadacidin has been studied for its anticancer activity. It operates as a metabolic inhibitor, specifically targeting enzyme-mediated reactions. The compound inhibits chloroplast formation in non-dividing, dark-grown Euglena cells, with the degree of inhibition proportional to the concentration in the medium. Its role in drug design extends to developing new inhibitors or activators to regulate adenylate synthase activity in the study of related diseases.
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| Enzyme Assay |
Cell-free enzyme assays for hadacidin typically involve measuring adenylosuccinate synthetase activity in the presence of the inhibitor. The ability of hadacidin to bind to purified adenylosuccinate synthetase can be demonstrated using anion-exchange HPLC and [formyl-¹⁴C]hadacidin. The binding of radiolabeled hadacidin to the enzyme can be quantified by co-elution studies. These assays confirm the competitive nature of the inhibition with respect to L-aspartate.
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| Cell Assay |
In vitro cellular assays for hadacidin involve treating cultured cancer cell lines with the compound to assess its antiproliferative effects. Cells are seeded in multi-well plates and exposed to various concentrations of hadacidin for a specified period. Cell viability is measured using standard assays such as MTT or CCK-8. The inhibition of AMP synthesis can be assessed by measuring nucleotide levels in treated cells. The compound's effects on cell growth and metabolism are then evaluated.
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| Animal Protocol |
In vivo animal studies for hadacidin are less extensively documented. The compound has been studied for its effects on chloroplast formation in Euglena cells. For anticancer research, animal models bearing tumor xenografts could be used to evaluate the compound's in vivo efficacy. The compound would be administered via appropriate routes, and tumor growth inhibition would be monitored. However, specific protocols for mammalian in vivo studies are not widely available in the literature.
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| ADME/Pharmacokinetics |
Hadacidin has a molecular weight of 119.08 and the formula C₃H₅NO₄. It is typically stored under recommended conditions as specified in the certificate of analysis. The compound is stable at room temperature for shipping within continental US. As a small molecule inhibitor of purine biosynthesis, its pharmacokinetic properties would be expected to include rapid absorption and distribution, with metabolism and excretion pathways typical of amino acid analogs.
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| References |
Tibrewal N, Elliott GI. Evaluation of hadacidin analogues. Bioorg Med Chem Lett. 2011 Jan 1;21(1):517-9. doi: 10.1016/j.bmcl.2010.10.088. Epub 2010 Oct 30. PubMed PMID: 21129960.
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| Additional Infomation |
Hadacidin is a monocarboxylic acid, a derivative of N-hydroxyglycine, in which the hydrogen atom bonded to the nitrogen atom is replaced by a formyl group. It was initially isolated from cultures of the common Penicillium frequentans. Hadacidin exhibits teratogenic, antitumor, and antibacterial effects, and also functions as a metabolite of Penicillium. It is a monocarboxylic acid, an N-hydroxy-α-amino acid, and an aldehyde compound.
Hadacidin is a controlled substance and may not be available for sale in certain territories. It is produced by Penicillium frequentans and has been used in drug design to help develop new inhibitors or activators to regulate adenylate synthase activity. The compound's mechanism involves N-oxygenation of glycine to yield N-hydroxyglycine followed by N-formylation to yield the hydroxamate. It has been studied as an inhibitor of adenine synthesis and is used in research on related diseases. |
| Molecular Formula |
C3H5NO4
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|---|---|
| Molecular Weight |
119.0761
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| Exact Mass |
119.022
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| CAS # |
689-13-4
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| Related CAS # |
689-13-4 (free); 2618-22-6 (sodium);
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| PubChem CID |
12717
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| Appearance |
Light yellow to light brown solid
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| Density |
1.592g/cm3
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| Boiling Point |
367.1ºC at 760 mmHg
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| Flash Point |
175.8ºC
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| Index of Refraction |
1.526
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| Source |
Originated from microorganisms: Escherichia coli
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| LogP |
-1.2
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
8
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| Complexity |
102
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(O)CN(O)C=O
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| InChi Key |
URJHVPKUWOUENU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C3H5NO4/c5-2-4(8)1-3(6)7/h2,8H,1H2,(H,6,7)
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| Chemical Name |
2-[formyl(hydroxy)amino]acetic acid
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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: ~25 mg/mL (~209.9 mM; with ultrasonication)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (20.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (20.99 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (20.99 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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.3977 mL | 41.9886 mL | 83.9772 mL | |
| 5 mM | 1.6795 mL | 8.3977 mL | 16.7954 mL | |
| 10 mM | 0.8398 mL | 4.1989 mL | 8.3977 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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