| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
The parent compound, Abamectin B1a, targets glutamate-gated chloride channels (GluCls) in invertebrates, which are critical for nervous system function. It binds to these channels with high affinity, causing increased chloride ion influx, leading to hyperpolarization of nerve and muscle cells, resulting in paralysis and death of parasites. The 8,9-Z isomer is structurally related to the parent compound and may have similar but potentially reduced activity due to the change in double bond geometry from trans (E) to cis (Z). The cis-isomer is often less biologically active due to altered conformation. This isomer is not the primary active ingredient; rather, it is a product of photodegradation.
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|---|---|
| ln Vitro |
In vitro, the specific activity of 8,9-Z-Abamectin B1a is less potent than the parent trans isomer. Abamectin B1a has an EC₅0 in the low nanomolar range (0.1-1 nM) in Caenorhabditis elegans motility assays. The cis-isomer is expected to have an EC₅0 10-100 times higher, making it significantly less active. In an MTT cytotoxicity assay using HepG2 cells, Abamectin B1a has an IC₅0 >100 uM, and the Z-isomer is likely similar. The compound is not a typical drug target inhibitor. It has no activity in mammalian systems at low concentrations due to the absence of glutamate-gated chloride channels in mammals. For environmental testing, it is used as a reference marker.
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| ln Vivo |
In vivo, 8,9-Z-Abamectin B1a is less toxic to pests than the parent E-isomer. The compound is used as a residue marker for regulatory compliance. The parent Abamectin B1a is widely used in veterinary medicine and agriculture. The Z-isomer is not used therapeutically. Its in vivo toxicology is similar to the parent but less potent. The conversion of the E-isomer to the Z-isomer is one of the degradation pathways of Abamectin in the environment (photodegradation). For impurity qualification, its presence indicates that the parent drug has been exposed to light and is potentially less effective.
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| Enzyme Assay |
General in vitro analytical protocol (HPLC-UV): For the analysis of Abamectin and its isomer, use a reverse-phase HPLC column (C18, 150×4.6 mm, 5 um). Mobile phase: acetonitrile:water (85:15, v/v). Flow rate: 1.0 mL/min. Detection: UV at 245 nm. Retention time for Abamectin B1a (E-isomer) is typically 8-10 min; retention time for 8,9-Z-Abamectin B1a is typically 6-7 min. This method is used to separate and quantify the isomers in degradation studies. For LC-MS/MS, use a positive ion mode (ESI+) with transitions specific to each isomer.
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| Cell Assay |
For in vitro toxicity assessment of the isomer, a standard MTT assay on HepG2 cells can be performed: seed cells in 96-well plates, treat with the compound (0.1, 1, 10, 100, 1000 uM) for 48 h, add MTT, and read at 570 nm. The IC₅0 is expected to be >100 uM, indicating low cytotoxicity. For a functional assay in nematodes (C. elegans), the Z-isomer can be tested for its ability to induce paralysis; it will be significantly less potent than the parent E-isomer.
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| Animal Protocol |
General in vivo (environmental) study for photodegradation: Dissolve Abamectin B1a (E-isomer) in a solvent (e.g., acetonitrile) and apply to a glass slide or soil sample. Expose to natural sunlight or a UV lamp (λ=254-365 nm) for 0-72 h. Extract the sample with acetonitrile and analyze by HPLC-UV or LC-MS. The formation of 8,9-Z-Abamectin B1a is monitored over time. The half-life of the E-isomer under UV light is typically a few hours. For a toxicology study in rats, administer 8,9-Z-Abamectin B1a (10, 50, 100 mg/kg, oral) to determine its acute toxicity. The LD₅0 is expected to be >1000 mg/kg, indicating low acute toxicity.
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| ADME/Pharmacokinetics |
The Z-isomer has different physicochemical properties from the E-isomer; it may have slightly lower logP and altered solubility. The parent Abamectin B1a is highly lipophilic (logP >4) and is readily absorbed after oral administration but is extensively metabolized by CYP3A4 in the liver. The Z-isomer is likely similar. The parent drug has a long half-life in animals (t½ ~1-2 days). The Z-isomer may have a shorter half-life due to faster metabolism or clearance. For research use, the isomer is supplied as a solid powder, stored at -20degC, and is soluble in DMSO, acetonitrile, and chloroform.
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| Toxicity/Toxicokinetics |
The toxicity of the Z-isomer is generally lower than that of the E-isomer due to its reduced potency at the GluCl receptor. It is not genotoxic. For impurity qualification in a drug substance, the limit is typically set according to the ICH Q3A/B guidelines. The parent Abamectin B1a has a high margin of safety in mammals.
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| References | |
| Additional Infomation |
Background: Abamectin is a mixture of avermectins (≥80% B1a and ≤20% B1b) and is widely used as an anthelmintic and insecticide. The compound is light-sensitive; exposure to ultraviolet light induces isomerization of the 8,9-double bond from the natural trans (E) configuration to the cis (Z) configuration. 8,9-Z-Abamectin B1a is a major photodegradation product. It is used as a reference standard for monitoring Abamectin residues in food and the environment. The compound is stored at -20degC and is for research use only.
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| Molecular Formula |
C48H72O14
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|---|---|
| Molecular Weight |
873.08
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| Exact Mass |
872.492
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| CAS # |
113665-89-7
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| PubChem CID |
138394064
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
3
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
62
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| Complexity |
1730
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| Defined Atom Stereocenter Count |
20
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| SMILES |
CC[C@H](C)[C@@H]1[C@H](C=C[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C\\4/CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\\C)C
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| InChi Key |
RRZXIRBKKLTSOM-WEWDGTPISA-N
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| InChi Code |
InChI=1S/C48H72O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3/b13-12+,27-15+,32-14-/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1
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| Chemical Name |
(1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'Z,20'R,21'R,24'S)-2-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
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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 |
| 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 | 1.1454 mL | 5.7269 mL | 11.4537 mL | |
| 5 mM | 0.2291 mL | 1.1454 mL | 2.2907 mL | |
| 10 mM | 0.1145 mL | 0.5727 mL | 1.1454 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
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