| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| Targets |
Mitoguazone primarily targets S-adenosylmethionine decarboxylase (SAMDC), an enzyme critical for polyamine biosynthesis. Polyamines are essential for cell proliferation, and their depletion leads to growth arrest and apoptosis. By competitively inhibiting SAMDC, Mitoguazone reduces the levels of polyamines, thereby disrupting cellular processes that depend on these molecules. The compound also exerts antimitochondrial effects, contributing to its cytotoxic activity. Its ability to induce p53-independent apoptosis makes it potentially effective in cancers with p53 mutations.
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| ln Vitro |
At doses as low as 0.5 μg/mL, mitoguazone competes with transcription factors for spermidine production. mitochondrial respiration and transcribed protein synthesis at 30 μg/mL or more [1]. Mitoguazone's capacity to cause cell irradiation by blocking the polyamine pathway was assessed in 2015 using scaffolded cadaver lines (MPC 3) and lines Raji, Ramos, and Daudi. Mitoguazone causes p53-independent programmed cell death in the human breast cancer MCF7 cell line and induces apoptosis in all human cadaveric cell lines in a concentration- and time-dependent manner [2].
In vitro, Mitoguazone induces apoptosis and triggers p53-independent programmed cell death in the MCF7 cell line. It has been shown to inhibit HIV DNA integration into the cellular DNA of monocytes and macrophages. Its cytotoxic activity is mediated through the inhibition of SAMDC and subsequent depletion of polyamines. These in vitro activities confirm its potential as an antineoplastic and antiviral agent. |
| ln Vivo |
Regardless of the trial period, the dosage AUC in mouse serum rose as a result of a decrease in mitoguazone's overall clearance. Furthermore, research has shown that medication levels in the kidneys, liver, and serum are higher in late stages of tumors when compared to early plasma without tumor control using specific instruments [5].
In vivo, Mitoguazone has been effective against myelogenous leukemia in experimental animals. It has been used in clinical trials for the treatment of lymphoma and non-Hodgkin lymphoma. Its efficacy in these settings supports its potential as a therapeutic agent for hematological malignancies. |
| Enzyme Assay |
The in vitro enzyme inhibition assay for Mitoguazone involves measuring the activity of S-adenosylmethionine decarboxylase (SAMDC) in the presence of the compound. The enzyme's activity is typically measured by quantifying the production of CO2 or decarboxylated S-adenosylmethionine from radiolabeled substrate. The IC50 for SAMDC inhibition is determined from dose-response curves.
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| Cell Assay |
Cellular assays for Mitoguazone involve treating cancer cell lines with the compound and measuring cell viability, proliferation, and apoptosis. The induction of apoptosis is assessed by measuring caspase activation, Annexin V staining, or DNA fragmentation. The compound's effects on polyamine levels are also measured using HPLC or other analytical methods.
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| Animal Protocol |
In vivo efficacy of Mitoguazone is evaluated in animal models of leukemia and lymphoma. The compound is administered intraperitoneally or intravenously, and tumor growth, survival, and biomarkers of polyamine depletion are assessed. These studies are crucial for determining its therapeutic potential.
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| ADME/Pharmacokinetics |
Mitoguazone has a molecular weight of 188.23 g/mol and a molecular formula of C5H12N8. Its melting point is 225°C (decomp). It is very soluble in water and relatively stable in acidic water but unstable in alkaline medium.
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| Toxicity/Toxicokinetics |
The toxicity profile of Mitoguazone is characteristic of cytotoxic agents. Side effects may include myelosuppression, gastrointestinal disturbances, and other toxicities associated with polyamine depletion. Comprehensive toxicological evaluations have been conducted in the context of clinical trials.
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| References |
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| Additional Infomation |
Mitoguazone is a hydrazone compound formed by the condensation of the two carbonyl groups of methylglyoxal with the primary amino groups of two molecules of aminoguanidine. It possesses antitumor activity, induces apoptosis, and acts as an inhibitor of S-adenosylmethionine decarboxylase (EC 4.1.1.50). It is a hydrazone compound belonging to the guanidine class. Its function is related to methylglyoxal and aminoguanidine. It is the conjugate base of Mitoguazone (2+). Mitoguazone has been used in clinical trials for the treatment of lymphoma, HIV infection, and non-Hodgkin's lymphoma. Mitoguazone is a guanidine hydrazone with potential antitumor activity. Mitoguazone competitively inhibits S-adenosyl-L-methionine decarboxylase (SAMD), an enzyme involved in polyamine synthesis, leading to reduced tumor cell proliferation, antimitochondrial effects, and induction of p53-independent apoptosis. Polyamines, particularly spermine and spermidine, are crucial for thymidine kinase production, DNA synthesis, and cell proliferation. (NCI04)
An antitumor drug, effective against myeloid leukemia in experimental animals. It is also an inhibitor of animal S-adenosylmethionine decarboxylase. Mitoguazone is an antineoplastic agent that has been investigated in clinical trials for the treatment of lymphoma and leukemia. It has not received widespread regulatory approval. Its mechanism involves inhibition of SAMDC and depletion of polyamines, leading to cell cycle arrest and apoptosis. |
| Molecular Formula |
C5H12N8
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|---|---|
| Molecular Weight |
184.20238
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| Exact Mass |
184.118
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| CAS # |
459-86-9
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| Related CAS # |
459-86-9 (free);7059-23-6 (dihydorchloride);
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| PubChem CID |
5351154
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| Appearance |
Light brown to brown solid powder
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| Density |
1.55g/cm3
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| Boiling Point |
436.6ºC at 760mmHg
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| Flash Point |
217.8ºC
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| Vapour Pressure |
7.99E-08mmHg at 25°C
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| Index of Refraction |
1.692
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| LogP |
0.696
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
13
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| Complexity |
264
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C(=N\N=C(N)N)/C=N/N=C(N)N
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| InChi Key |
MXWHMTNPTTVWDM-NXOFHUPFSA-N
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| InChi Code |
InChI=1S/C5H12N8/c1-3(11-13-5(8)9)2-10-12-4(6)7/h2H,1H3,(H4,6,7,12)(H4,8,9,13)/b10-2+,11-3+
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| Chemical Name |
2-[(E)-[(1E)-1-(diaminomethylidenehydrazinylidene)propan-2-ylidene]amino]guanidine
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| Synonyms |
methylG; MeGAG; Mitoguazone
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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) |
H2O : ~50 mg/mL (~271.44 mM)
DMSO : ~8.33 mg/mL (~45.22 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 4 mg/mL (21.72 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.4289 mL | 27.1444 mL | 54.2888 mL | |
| 5 mM | 1.0858 mL | 5.4289 mL | 10.8578 mL | |
| 10 mM | 0.5429 mL | 2.7144 mL | 5.4289 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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