Simetryn
Based on 1 Customer Validation
Simetryn is a triazine herbicide that exerts teratogenicity. Simetryn inhibits photosynthesis by blocking electron transfer in the chloroplast photosystem II and activates the MEK/Erk signaling pathway. Simetryn triggers vascular and developmental abnormalities in zebrafish and tadpoles, suppresses proliferation, enhances apoptosis, and induces malformations. Simetryn serves as a tool to establish a zebrafish model for studying arteriovenous malformations and related pathogenesis. Simetryn controls paddy weeds and can be used for research on developmental and vascular disorders.
For research use only. We do not sell to patients.
- Purity : 99.75%
- CAS No.: 1014-70-6
- Formula: C8H15N5S
- Molecular Weight:213.30
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocols
- Purity & Documentation
- References
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Help & FAQs
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Biological Activity
Description
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:AB, Tg(fli1a:GFP), Tg(gata1:Dsred), Tg(Flk1:GFP), Tg(kdrl:mcherry), Tg(lyve1b:YFP) (8-10 h post-fertilization embryos)[1]
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Dosage:10 mg/L, 15 mg/L, 20 mg/L
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Administration:waterborne exposure; continuous; 48 hours
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Result:Induced blood stasis and abnormal artery-vein capillary fusion in the caudal vascular plexus (CVP).
Significantly increased dorsal aorta and largest venous diameters compared to controls at 48 hours post-exposure (10, 15, and 20 mg/L).
Caused erythrocyte accumulation at arteriovenous junctions in the CVP.
Reduced PH3-positive proliferating cells and increased TUNEL-positive apoptotic cells in the CVP in a concentration-dependent manner.
Upregulated p53 mRNA expression.
Impaired cerebral vascular development, with absence of the dorsal longitudinal vein and reduced central venous bud.
Induced abnormal morphology and reduced fluorescent signal intensity in caudal lymphatic vessels.
Increased phosphorylated Erk (p-Erk) and total Erk protein levels.
Chemical Information
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CAS No. 1014-70-6
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Appearance Solid
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Molecular Weight 213.30
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Formula C8H15N5S
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Color White to off-white
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SMILES
CSC1=NC(NCC)=NC(NCC)=N1
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 2 years -20°C 1 year
Solvent & Solubility
In Vitro:
DMSO : ≥ 37 mg/mL (173.46 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (11.72 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocols
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Reproductive and Developmental Toxicity Study
Reproductive and developmental toxicity studies detect adverse effects of prenatal or peri/postnatal exposure on maternal condition, pregnancy maintenance, embryo-fetal survival, fetal growth, structural development, and offspring reproductive or developmental endpoints; classic rat protocols generate readouts by comparing treated groups with vehicle, pair-fed, or untreated controls for implantation, resorption, fetal weight, crown-rump length, external morphology, visceral morphology, skeletal ossification, anogenital distance, nipple/areola retention, and postnatal cohort outcomes.
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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How to Select a Suitable Non-Mouse Animal Model
Selecting a suitable non-mouse animal model is a structured decision based on the research question, required anatomy or physiology, disease mechanism, endpoint feasibility, translational relevance, and ethical justification. Non-mouse models are preferred when mice cannot reproduce key human-relevant features, such as organ size, surgical anatomy, cardiovascular physiology, neuroanatomy, immune features, pharmacology, toxicology, or long-term clinical procedures. Candidate species may include rats, rabbits, guinea pigs, ferrets, zebrafish, pigs, sheep, goats, dogs, cats, horses, and non-human primates, but each species must be justified by its specific scientific advantage rather than convenience or tradition. Unresolved questions include how to quantify translational superiority across species, how to balance increased biological relevance against higher ethical burden, and when human-derived systems or new approach methodologies should replace animal use.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
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Cell Viability Determination by MTT Colorimetric Assay
The following protocol uses the MTT colorimetric assay as a classic literature-established method for assessing cell viability/metabolic activity in cultured mammalian cells. MTT[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] is reduced by metabolically active cells to a colored formazan product; the amount of formazan is quantified spectrophotometrically and provides an indirect measure of metabolically active viable cells. Importantly, MTT reduction reflects cellular oxidoreductase/metabolic activity rather than an absolute direct count of living cells, so changes in cellular metabolism can alter the signal independently of cell number.
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How to Choose the Right Model Animal
Choosing the right model animal is a validity-driven decision in which the species, strain, sex, age, genetic background, disease-induction method, outcome measures, and welfare burden must match the scientific question rather than laboratory tradition or convenience. A model should be selected by judging face validity, construct validity, and predictive validity: whether it resembles the human phenotype, whether it reproduces relevant mechanisms, and whether results are likely to predict human biology or treatment response. Animal studies often fail to translate because of species differences, weak disease resemblance, poor experimental design, inadequate reporting, publication bias, and underuse of randomization, blinding, and sample-size justification. Unresolved questions include how to rank competing models objectively, how much human-disease complexity must be reproduced for a given objective, and when non-animal systems such as organoids, ex vivo tissue, or computational models
Purity & Documentation
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Data Sheet (272 KB)
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SDS (597 KB)
- English - EN (597 KB)
- Français - FR (597 KB)
- Deutsch - DE (597 KB)
- Norwegian - NO (597 KB)
- Español - ES (597 KB)
- Swedish - SV (597 KB)
- Italian - IT (597 KB)
- Korean - KR (597 KB)
- Portuguese - PT (597 KB)
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Handling Instructions (2659 KB)
References
[1]. Xiao Z, et al. Simetryn induces arteriovenous malformations in zebrafish embryos through activation of Erk signaling. Biochem Biophys Res Commun. 2026;804:153339. [Content Brief]
[2]. Saka M, et al. Application of an amphibian (Silurana tropicalis) metamorphosis assay to the testing of the chronic toxicity of three rice paddy herbicides: simetryn, mefenacet, and thiobencarb. Ecotoxicol Environ Saf. 2013;92:135-143. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 4.6882 mL | 23.4412 mL | 46.8823 mL | 117.2058 mL |
| 5 mM | 0.9376 mL | 4.6882 mL | 9.3765 mL | 23.4412 mL | |
| 10 mM | 0.4688 mL | 2.3441 mL | 4.6882 mL | 11.7206 mL | |
| 15 mM | 0.3125 mL | 1.5627 mL | 3.1255 mL | 7.8137 mL | |
| 20 mM | 0.2344 mL | 1.1721 mL | 2.3441 mL | 5.8603 mL | |
| 25 mM | 0.1875 mL | 0.9376 mL | 1.8753 mL | 4.6882 mL | |
| 30 mM | 0.1563 mL | 0.7814 mL | 1.5627 mL | 3.9069 mL | |
| 40 mM | 0.1172 mL | 0.5860 mL | 1.1721 mL | 2.9301 mL | |
| 50 mM | 0.0938 mL | 0.4688 mL | 0.9376 mL | 2.3441 mL | |
| 60 mM | 0.0781 mL | 0.3907 mL | 0.7814 mL | 1.9534 mL | |
| 80 mM | 0.0586 mL | 0.2930 mL | 0.5860 mL | 1.4651 mL | |
| 100 mM | 0.0469 mL | 0.2344 mL | 0.4688 mL | 1.1721 mL |
Simetryn Related Classifications
HY-B1853 Related Classifications
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Keywords
- Simetryn
- 1014-70-6
- Environmental Pollutants
- Herbicide
- ERK
- Apoptosis
- MEK
- zebrafish embryos
- S1-RSA
- chloroplast photosystem II electron transport chain
- BALB/c mice
- freshwater plankton communities
- Silurana tropicalis tadpoles
- MEK/Erk signaling cascade
- arteriovenous malformations
- scoliosis
- Erk protein
- Inhibitor
- inhibitor
- inhibit