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| Targets |
The primary target of Jarin-1 is jasmonic acid-amido synthetase (JAR1), an enzyme that catalyzes the conjugation of jasmonic acid (JA) with isoleucine (Ile) to form the bioactive hormone jasmonoyl-isoleucine (JA-Ile). JA-Ile is a key signaling molecule in the jasmonate pathway, which regulates plant defense responses against herbivores and pathogens, as well as various developmental processes. Jarin-1 is a selective inhibitor of JAR1 with an IC50 of 3.8 μM. By blocking JAR1 activity, Jarin-1 specifically prevents the biosynthesis of JA-Ile, making it a valuable probe for dissecting jasmonate signaling pathways in plants.
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| ln Vitro |
Strawberries treated with MeJA had higher peel and anthocyanin levels than those treated with Jarin-1; these differences were accompanied by the activation of the FaANS and FaUFGT genes. As it turned out, fruits treated with Jarin-1 and MeJA + Jarin-1 had higher proanthocyanidin (PA) contents than fruits treated with MeJA. Treatment with MeJA + Jarin-1 increased the expression of FaANR and associated transcription factors, including FabHLH33, FaMYB9/11, FaJMT, and FaJAR1.2. The FaMYB1/9/10/11 genes' promoter region had JA response elements. Strawberries accumulate more PA because extracting Jarin-1 from MeJA-treated fruits can control genes involved in PA production [1].
In vitro, Jarin-1 inhibits JAR1 enzyme activity with an IC50 of 3.8 μM. It specifically inhibits bioactive JA-Ile biosynthesis in Arabidopsis and other plants. The compound impairs the activity of JA-Ile synthetase, thereby preventing the synthesis of the active hormone, JA-Ile, whereas closely related enzymes are not affected. This selectivity makes Jarin-1 a valuable tool for studying the specific roles of JA-Ile in plant physiology. |
| ln Vivo |
In vivo, Jarin-1 inhibits jasmonate responses in Arabidopsis thaliana. By blocking JAR1 activity, the compound prevents the synthesis of bioactive JA-Ile, thereby suppressing jasmonate signaling in plants. In strawberry fruit, Jarin-1 has been used to study the role of jasmonate signaling in fruit development and ripening. The compound's ability to modulate plant defense responses suggests potential applications in agriculture for controlling pest resistance and stress responses.
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| Enzyme Assay |
For JAR1 inhibitors, standard cell-free assays involve measuring the enzyme activity of recombinant JAR1 using jasmonic acid and isoleucine as substrates. The formation of JA-Ile is measured by LC-MS or radiolabeled methods to determine IC50 values. The selectivity of the inhibitor for JAR1 over related enzymes is assessed using enzyme assays for other JA-conjugating enzymes.
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| Cell Assay |
For JAR1 inhibitors, standard cellular assays in plants involve treatment of Arabidopsis seedlings or other plant tissues with the test compound. JA-Ile levels in plant tissues are measured by LC-MS. Jasmonate-responsive gene expression (e.g., PDF1.2, VSP2) is assessed by qPCR. Plant defense responses and developmental phenotypes are monitored.
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| Animal Protocol |
For in vivo evaluation of JAR1 inhibitors, standard plant models include Arabidopsis thaliana, tomato, or strawberry plants. The compound is typically applied as a solution to plant tissues or through the roots. Jasmonate responses, defense gene expression, and phenotypic changes are assessed. Jarin-1 has been used in strawberry fruit studies.
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| ADME/Pharmacokinetics |
Jarin-1 has a molecular weight of 471.55 and formula C28H29N3O4. The chemical name is N-[(1R,9S)-11-(3-methoxypropanoyl)-6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-5-yl]-[1,1'-biphenyl]-4-carboxamide. It is soluble in DMSO at 33.33 mg/mL and has a purity of 98% by HPLC.
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| Toxicity/Toxicokinetics |
Detailed toxicology data for Jarin-1 is not provided in the available sources. As a research compound primarily used for plant biology studies, standard toxicological evaluation for therapeutic applications would be required. The compound is for research use only and not for therapeutic applications.
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| References |
[1]. Delgado LD, et al. Application of a JA-Ile Biosynthesis Inhibitor to Methyl Jasmonate-Treated Strawberry Fruit Induces Upregulation of Specific MBW Complex-Related Genes and Accumulation of Proanthocyanidins. Molecules. 2018 Jun 13;23(6). pii: E1433.
[2]. Meesters C, et al. A chemical inhibitor of jasmonate signaling targets JAR1 in Arabidopsis thaliana. Nat Chem Biol. 2014 Oct;10(10):830-6. |
| Additional Infomation |
Jarin-1 is a selective inhibitor of jasmonic acid-amido synthetase (JAR1) with an IC50 of 3.8 μM. It is the first small-molecule inhibitor of JAR1 that specifically inhibits bioactive JA-Ile biosynthesis in Arabidopsis and other plants. The compound is a valuable probe for dissecting jasmonate signaling pathways in plants. No regulatory approval for therapeutic use has been identified.
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| Molecular Formula |
C28H29N3O4
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| Molecular Weight |
471.547567129135
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| Exact Mass |
471.215
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| CAS # |
1212704-51-2
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| PubChem CID |
7142742
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| Appearance |
White to off-white solid powder
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| LogP |
2.6
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
35
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| Complexity |
883
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| Defined Atom Stereocenter Count |
2
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| SMILES |
COCCC(=O)N1C[C@@H]2C[C@H](C1)C3=CC=C(C(=O)N3C2)NC(=O)C4=CC=C(C=C4)C5=CC=CC=C5
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| InChi Key |
LMVUVKIGGHXSJX-WMZHIEFXSA-N
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| InChi Code |
InChI=1S/C28H29N3O4/c1-35-14-13-26(32)30-16-19-15-23(18-30)25-12-11-24(28(34)31(25)17-19)29-27(33)22-9-7-21(8-10-22)20-5-3-2-4-6-20/h2-12,19,23H,13-18H2,1H3,(H,29,33)/t19-,23+/m0/s1
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| Chemical Name |
N-[(1R,9S)-11-(3-methoxypropanoyl)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-5-yl]-4-phenylbenzamide
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| Synonyms |
Jarin1; Jarin 1; Jarin-1
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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) |
DMSO : ~33.33 mg/mL (~70.68 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1207 mL | 10.6033 mL | 21.2067 mL | |
| 5 mM | 0.4241 mL | 2.1207 mL | 4.2413 mL | |
| 10 mM | 0.2121 mL | 1.0603 mL | 2.1207 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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