| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
Macrozamin itself does not have a therapeutic target; its primary biological interaction is with cellular DNA after metabolic conversion. The metabolite MAM alkylates DNA at guanine residues, leading to mutations and cytotoxicity. It targets rapidly dividing cells and can induce cancer in the liver, kidney, and nervous system. It also inhibits protein synthesis and causes oxidative stress.
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|---|---|
| ln Vitro |
In vitro, macrozamin is not directly active; its toxicity requires enzymatic hydrolysis by β-glucosidase to release MAM. MAM is highly cytotoxic to various cell lines (e.g., HepG2, neuroblastoma) with IC50 values around 10-50 µM after 24 h. It induces DNA strand breaks and apoptosis. Macrozamin itself shows no significant activity in cell-free assays without β-glucosidase.
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| ln Vivo |
In vivo, macrozamin is highly toxic. In rodents, oral administration at doses of 50-100 mg/kg causes severe hepatotoxicity, neurotoxicity, and death. Chronic exposure leads to liver and kidney tumors. It is also a potent neurotoxin, causing ataxia and paralysis in cattle and other animals that consume cycad plants. No therapeutic effects are known.
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| Enzyme Assay |
The in vitro activation assay uses recombinant β-glucosidase to convert macrozamin to MAM. The enzyme is incubated with macrozamin (1-100 µM) in acetate buffer (pH 5.0) at 37°C for 1 h. The released MAM is quantified by HPLC. For DNA alkylation studies, calf thymus DNA is incubated with the reaction mixture, and adducts are measured by LC-MS/MS.
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| Cell Assay |
In vitro cell-based assays are performed using HepG2 or neuroblastoma cells. Cells are treated with macrozamin (0.1-100 µM) for 24-48 h. Cytotoxicity is measured by LDH release or MTT assay. DNA damage is assessed by comet assay. Since macrozamin requires activation, some studies add β-glucosidase to the culture medium. Apoptosis is evaluated by caspase-3 activity.
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| Animal Protocol |
In vivo toxicity studies in rats involve oral gavage of macrozamin at doses of 10-50 mg/kg. Animals are observed for signs of neurotoxicity and hepatotoxicity. Blood samples are collected for liver enzyme analysis. Histopathology of liver, kidney, and brain is performed. For carcinogenicity studies, chronic administration (1-5 mg/kg/day for 1 year) is used to assess tumor incidence.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for macrozamin are limited. In rats, after oral administration, macrozamin is absorbed and rapidly converted to MAM in the intestine. MAM has a half-life of about 2 h. The compound is distributed to the liver, kidney, and brain. Excretion is primarily via urine as metabolites. Bioavailability is estimated at 50-70%.
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| Toxicity/Toxicokinetics |
Macrozamin is highly toxic; the oral LD50 in rats is approximately 100 mg/kg. It is mutagenic and carcinogenic (IARC Group 2B). Chronic exposure causes neurotoxicity, hepatotoxicity, and nephrotoxicity. It is also teratogenic in animal studies. No safe exposure level is established. It is considered a hazardous substance and requires strict handling precautions.
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| References | |
| Additional Infomation |
Macrozamin has reportedly been found in Dioon spinulosum, Stangeria eriopus, and other organisms with available data.
Macrozamin is a major toxin in cycad plants, which are used as food in some traditional cultures after extensive processing to remove toxins. It is also a known cause of Guam's amyotrophic lateral sclerosis/parkinsonism-dementia complex (ALS/PDC) when consumed in contaminated diets. It is not used in medicine; its study is relevant to food safety and toxicology. |
| Molecular Formula |
C13H24N2O11
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|---|---|
| Molecular Weight |
384.3365
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| Exact Mass |
384.138
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| CAS # |
6327-93-1
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| PubChem CID |
122803
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| Appearance |
White to off-white solid powder
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| Density |
1.862g/cm3
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| Boiling Point |
660.381ºC at 760 mmHg
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| Melting Point |
237-238 °C
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| Flash Point |
353.186ºC
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| Index of Refraction |
1.655
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| LogP |
-4.5
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
26
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| Complexity |
481
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| Defined Atom Stereocenter Count |
9
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| SMILES |
C[N+](=NCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O)O)O)[O-]
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| InChi Key |
DQCANINXHQSIAW-OCFMYHKXSA-N
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| InChi Code |
InChI=1S/C13H24N2O11/c1-15(22)14-4-25-13-11(21)9(19)8(18)6(26-13)3-24-12-10(20)7(17)5(16)2-23-12/h5-13,16-21H,2-4H2,1H3/t5-,6-,7+,8-,9+,10-,11-,12+,13-/m1/s1
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| Chemical Name |
methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethylimino]azanium
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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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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) |
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
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|---|---|
| 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 | 2.6019 mL | 13.0093 mL | 26.0186 mL | |
| 5 mM | 0.5204 mL | 2.6019 mL | 5.2037 mL | |
| 10 mM | 0.2602 mL | 1.3009 mL | 2.6019 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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