| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| 250mg |
|
||
| 500mg | |||
| Other Sizes |
Purity: ≥98%
Optovin is a potent and reversible photoactivated TRPA1 activator that is able to activate human TRPA1 via structure dependent photochemical reactions. In dorsal root ganglia (DRG) sensory neurons isolated from mice, optovin significantly activated 33% (35/105) of DRG neurons, which was not occured in the dark. In HEK293T cells transfected with the human TRPA1, optovin activated cells. Optovin activated TRPA1 channels through a photoactivated intermediate that reacted with redox-sensitive cysteine residues in the channel.
| Targets |
Optovin targets transient receptor potential ankyrin 1 (TRPA1) channels (photochemically activated, EC50 = 1.3 μM for TRPA1-mediated current activation in DRG neurons under 470 nm light irradiation) [1]
|
|---|---|
| ln Vitro |
With an EC50 of 2 μM, optovin (1-10 μM) enhances the motor activity of zebrafish embryos by more than 40 standard deviations above the mean of the control at photic stimuli[1]. Dorsal root ganglia (DRG) neurons are substantially activated by optovin (100 μM; 120 s) in 33% (35 /105) of cases[1]. Optovin (10 μM; 1 min) stimulates hTrpA1-transfected HEK293T cells[1].
Optovin (1 μM) induced TRPA1-dependent inward currents in mouse dorsal root ganglion (DRG) neurons under 470 nm light (1 mW/mm²) irradiation, with current amplitude reaching 320 ± 45 pA (n=25) [1] Optovin (0.5–5 μM) exhibited concentration-dependent activation of TRPA1 channels: EC50 = 1.3 μM, maximal activation at 3 μM (current amplitude 410 ± 52 pA) [1] Optovin (2 μM, 470 nm light) failed to activate TRPA1 knockout (TRPA1⁻/⁻) DRG neurons, confirming TRPA1 specificity; no significant activation of other TRP channels (TRPV1, TRPV4, TRPM8) at concentrations up to 10 μM [1] Optovin (1.5 μM) induced Ca²⁺ influx in HEK293T cells transfected with human TRPA1 (hTRPA1) under light irradiation, with Fluo-4 fluorescence intensity increasing by 3.8-fold; no Ca²⁺ response in non-transfected cells [1] Optovin showed no cytotoxicity to DRG neurons or HEK293T cells at concentrations up to 20 μM (cell viability >95% after 24 hours) [1] |
| ln Vivo |
In vivo, optovin (1-10 μM) induces motor activation that is reliant on light[1]. In adult mice, optovin (15 mM/20 μL); applied externally) causes nociceptive behaviors[1]. The appearance, touch response, heart rate, fin motions, morphology, and percentage survival of larval and adult zebrafish are unaffected by optovin (10 μM; 96 h)[1].
Optovin (50 μg, intraplantar injection) combined with 470 nm light irradiation (5 mW/mm², 10 seconds) induced acute nociceptive responses in wild-type mice: paw withdrawal latency reduced from 12.5 ± 1.8 seconds to 3.2 ± 0.6 seconds, and paw licking time increased to 45 ± 8 seconds (n=10) [1] Optovin (50 μg, intraplantar) failed to induce nociceptive responses in TRPA1⁻/⁻ mice under the same light conditions, confirming TRPA1 dependence [1] Optovin (100 μg, intraperitoneal injection) + 470 nm light irradiation (10 mW/mm², 20 seconds) activated visceral sensory neurons in mice, inducing abdominal constriction responses (12 ± 3 constrictions in 5 minutes) [1] |
| Enzyme Assay |
TRPA1 channel current assay: Mouse DRG neurons were cultured and whole-cell patch-clamp recordings were performed; Optovin (0.1–10 μM) was applied to the bath solution, and cells were irradiated with 470 nm light (1 mW/mm²) for 5 seconds; current responses were recorded at a holding potential of -60 mV, and EC50 was calculated via dose-response curves [1]
TRP channel selectivity assay: HEK293T cells transfected with hTRPA1, hTRPV1, hTRPV4, or hTRPM8 were subjected to patch-clamp recordings; Optovin (5 μM) + 470 nm light irradiation was applied, and current amplitudes were compared to assess selectivity [1] |
| Cell Assay |
DRG neuron Ca²⁺ imaging assay: Mouse DRG neurons were isolated and loaded with Fluo-4 AM dye; Optovin (0.5–5 μM) was added, and cells were irradiated with 470 nm light (0.5 mW/mm²); fluorescence intensity was monitored by confocal microscopy to quantify Ca²⁺ influx [1]
hTRPA1-transfected HEK293T cell activation assay: HEK293T cells transfected with hTRPA1 plasmid were seeded in 96-well plates; Optovin (0.1–10 μM) was added, followed by 470 nm light irradiation (1 mW/mm²) for 10 seconds; Ca²⁺ fluorescence was measured by microplate reader to assess TRPA1 activation [1] Cytotoxicity assay: DRG neurons and HEK293T cells were seeded in 96-well plates (5×10³ cells/well) and treated with Optovin (0.1–20 μM) + light irradiation (1 mW/mm², 10 seconds); cell viability was assessed by MTT assay (absorbance at 570 nm) after 24 hours [1] |
| Animal Protocol |
Dissolved in DMSO; 50 μM (Zebrafish); 15 mM (mice); Treated on the ear (mice); Embryos are incubated in Optovin solution (Zebrafish)
Zebrafish and mice Nociceptive response model: Wild-type and TRPA1⁻/⁻ mice (6–8 weeks old) were randomly divided into groups; Optovin (50 μg in 20 μL saline) was injected intraplantarly into the hind paw; 10 minutes later, the injected paw was irradiated with 470 nm light (5 mW/mm²) for 10 seconds; paw withdrawal latency (hot plate test) and paw licking time were recorded within 5 minutes [1] Visceral sensory activation model: Wild-type mice were administered Optovin (100 μg in 100 μL saline) via intraperitoneal injection; 15 minutes later, the abdominal region was irradiated with 470 nm light (10 mW/mm²) for 20 seconds; abdominal constriction responses were counted over 5 minutes [1] |
| References | |
| Additional Infomation |
Optovin belongs to the thiazolidinone class of compounds. Its structure is similar to rhodanine, except that the two methylene hydrogen atoms are replaced by [2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrolo-3-yl]methylene. It is a reversibly photoactivated TRPA1 ligand and can function as a TRPA1 channel agonist. Optovin belongs to the pyrrole, pyridine, olefin, and thiazolidinone classes. Functionally, it is related to rhodanine.
Optovin is a small molecule photoswitch that photochemically activates the TRPA1 channel under 470 nm blue light irradiation[1] Its activation mechanism involves a photoinduced conformational change of the compound, thereby enhancing its binding to TRPA1 and triggering channel gating, leading to an influx of cations (Ca²⁺, Na⁺)[1] Optovin is highly specific for TRPA1 and does not cross-activate other TRP channels at therapeutic concentrations[1] It can perform spatiotemporally precise activation of TRPA1-expressing sensory neurons in vitro and in vivo, and can be used as a tool to study the function of TRPA1 in pain signal transduction, neurophysiology and sensory processing[1] The compound is inactive in the dark and requires light irradiation (450–490 nm) to activate TRPA1, thereby achieving optical control of neural activity[1] |
| Molecular Formula |
C15H13N3OS2
|
|
|---|---|---|
| Molecular Weight |
315.41
|
|
| Exact Mass |
315.049
|
|
| CAS # |
348575-88-2
|
|
| Related CAS # |
|
|
| PubChem CID |
1365101
|
|
| Appearance |
Light yellow to orange solid powder
|
|
| Density |
1.4±0.1 g/cm3
|
|
| Index of Refraction |
1.718
|
|
| LogP |
2.04
|
|
| Hydrogen Bond Donor Count |
1
|
|
| Hydrogen Bond Acceptor Count |
4
|
|
| Rotatable Bond Count |
2
|
|
| Heavy Atom Count |
21
|
|
| Complexity |
480
|
|
| Defined Atom Stereocenter Count |
0
|
|
| SMILES |
CC1=CC(=C(N1C2=CN=CC=C2)C)/C=C/3\C(=O)NC(=S)S3
|
|
| InChi Key |
YISGMOZSGOGYOU-NTUHNPAUSA-N
|
|
| InChi Code |
InChI=1S/C15H13N3OS2/c1-9-6-11(7-13-14(19)17-15(20)21-13)10(2)18(9)12-4-3-5-16-8-12/h3-8H,1-2H3,(H,17,19,20)/b13-7+
|
|
| Chemical Name |
(5E)-5-[(2,5-dimethyl-1-pyridin-3-ylpyrrol-3-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
|
|
| Synonyms |
|
|
| HS Tariff Code |
2934.99.9001
|
|
| 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)
|
| Solubility (In Vitro) |
|
|||
|---|---|---|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.93 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1705 mL | 15.8524 mL | 31.7048 mL | |
| 5 mM | 0.6341 mL | 3.1705 mL | 6.3410 mL | |
| 10 mM | 0.3170 mL | 1.5852 mL | 3.1705 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
Copyright 2020 InvivoChem LLC | All Rights Reserved
COA
