| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
||
| 250mg |
|
||
| 500mg |
|
||
| 1g |
|
||
| 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.
|
|---|---|
| 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.
|
| 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.
|
| 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.
|
| 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.
|
| 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.
|
| 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.
|
| 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.
|
| 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
|
|---|---|
| Molecular Weight |
119.0761
|
| Exact Mass |
119.022
|
| CAS # |
689-13-4
|
| Related CAS # |
689-13-4 (free); 2618-22-6 (sodium);
|
| PubChem CID |
12717
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.592g/cm3
|
| Boiling Point |
367.1ºC at 760 mmHg
|
| Flash Point |
175.8ºC
|
| Index of Refraction |
1.526
|
| LogP |
-1.2
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
8
|
| Complexity |
102
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C(O)CN(O)C=O
|
| InChi Key |
URJHVPKUWOUENU-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C3H5NO4/c5-2-4(8)1-3(6)7/h2,8H,1H2,(H,6,7)
|
| Chemical Name |
2-[formyl(hydroxy)amino]acetic acid
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
COA