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Optovin

Alias: (Z)-5-((2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl)methylene)-2-thioxothiazolidin-4-one
Cat No.:V1910 Purity: ≥98%
Optovin is a potent and reversible photoactivated TRPA1 activator that is able to activate human TRPA1 via structure dependent photochemical reactions.
Optovin
Optovin Chemical Structure CAS No.: 348575-88-2
Product category: TRP Channel
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

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.

Biological Activity I Assay Protocols (From Reference)
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].
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].
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
References

[1]. Photochemical activation of TRPA1 channels in neurons and animals. Nat Chem Biol. 2013 Apr;9(4):257-63.

Additional Infomation
Optovin is a member of the class of thiazolidinone that is rhodanine in which the two methylene hydrogens have been replaced by a 2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl]methylidene group. A TRPA1 ligand that can be reversibly photoactivated. It has a role as a TRPA1 channel agonist. It is a member of pyrroles, a member of pyridines, an olefinic compound and a thiazolidinone. It is functionally related to a rhodanine.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H13N3OS2
Molecular Weight
315.41
Exact Mass
315.049
CAS #
348575-88-2
Related CAS #
348575-88-2
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
(Z)-5-((2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl)methylene)-2-thioxothiazolidin-4-one
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 Data
Solubility (In Vitro)
DMSO:63 mg/mL (199.74 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
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.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Biological Data
  • Optovin structure activity relationship analysis (a) Horizontal bar plot showing behavioral excitation scores from groups treated with the indicated optovin analogs (n=5). Optovin, 6b8, 6c1, 6c4 and 4g6 analogs are active; 6c5, 6c7,6c2, and 6c3 are inactive. Differences between active and inactive groups are significant, p<0.001. Structures of the analogs are shown to the left of the bar plot. All compounds were tested at 10 μM, except for the 4g6 analog, which was tested at 100 μM. (b) Example responses from the indicated groups. Red vertical lines indicate light stimuli. Green horizontal lines indicate the off-latency duration for motor responses following each stimulus. (c) Bar plot showing average behavioral response duration of groups treated with the indicated optovin analogs. Values are means ± standard deviations (n=5). Differences between optovin and 4g6 and 6b8 are significant, p<0.01.[1].Nat Chem Biol. 2013 Apr;9(4):257-63.
  • TRPA1 is necessary and sufficient for the optovin response (a) Percentage of mouse DRG neurons responding to the indicated treatments. In wild type, the light stimulus activated 30% of neurons assayed (35/105). In the TRPA1-KO neurons, the total percentage of responding neurons was 2.7% (8/291). (b) Behavioral excitation scores during the optovin response for zebrafish of the indicated genotypes. (c) Behavioral excitation scores calculated for WT, heterozygous and homozygous TrpA1b mutant animals (n=21, 23 and 16 respectively) during the PMR (control) and optovin response assays. Homozygous mutant animals show a significantly lower activity during the optovin response assay, p<0.001. (d) Bar plot showing calcium indicator dye fluorescence in cells transfected with GFP or hTrpA1 before and after a 2 min treatment with optovin and light (n=130, 120 cells). The difference between treated and untreated hTRPA1 transfected cells is significant, p<0.001.[1].Nat Chem Biol. 2013 Apr;9(4):257-63.
  • Optovin activates TRPA1 via structure dependent photochemical reactions (a) Optovin's absorbance (UV-Vis) at the indicated wavelengths. (b) Fluorescence of the singlet oxygen indicator dye SOG with and without optovin at the indicated light intensities. (c) Behavioral excitation scores from animals treated with the indicated compounds (n=5 wells). Wells treated with optovin and 7c7 are significantly higher than DMSO treated controls, p<0.001). The difference between DMSO and 7d1 is not significant, p=0.8. Abbreviated names of singlet oxygen generators: Hyper, Hypericin; AO, acridine orange; MC, merocyanine 540; RB, rose Bengal. (d) Calcium indicator fluorescence before and after optovin treatment in cells transfected with the GFP, hTRPA1 or the indicated hTRPA1 mutant construct. (e) Barplot quantifying the calcium response 1 min after optovin treatment (n=130, 120, 107, 111, 75 cells respectively) (**p<0.01, ***p<0.0001). (f) Structures of the analogs are shown. Note that the olefin is methylated in analog 7d1. All compounds were tested at 10 μM.[1].Nat Chem Biol. 2013 Apr;9(4):257-63.
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