IUPAC/Chemical Name
(Z)-5-((2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl)methylene)-2-thioxothiazolidin-4-one
InChi Key
YISGMOZSGOGYOU-QPEQYQDCSA-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-
SMILES Code
O=C1NC(S/C1=C\C2=C(C)N(C3=CC=CN=C3)C(C)=C2)=S
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Optovin is a reversible photoactivated TRPA1 ligand that enables light-mediated neuronal excitation.
In vitro activity:
This study found that optovin generates singlet oxygen (1O2), but neither hydroxyl radicals nor superoxide (Fig. 4b and Supplementary Fig. 11). Together, these data suggest that light excites optovin to a photochemically reactive state that can activate TRPA1 either directly or via singlet oxygen. Neither catalase nor superoxide dismutase reduced optovin's effects on hTRPA1 transfected HEK cells (Supplementary Fig. 12), further suggesting that hydroxyl radicals and superoxide do not contribute to optovin's activity.
Reference: Nat Chem Biol. 2013 Apr;9(4):257-63. https://pubmed.ncbi.nlm.nih.gov/23396078/
In vivo activity:
Optovin is a rhodanine-containing small molecule with no previously annotated biological activity. Whereas DMSO-treated animals do not respond to photic stimuli, optovin-treated animals respond to light with vigorous motor excitation at an EC50 of 2 μM (Fig. 1d). Motor behavior in optovin-treated animals is elicited by stimulus intensities greater than 1.6 μW*mm−2 (Fig. 1e). Thus, optovin is a novel behavior-modifying compound that causes rapid and reversible motor excitation in response to violet light stimuli.
Reference: Nat Chem Biol. 2013 Apr;9(4):257-63. https://pubmed.ncbi.nlm.nih.gov/23396078/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
25.0 |
79.26 |
|
| DMF:PBS (pH 7.2) (1:6) |
0.1 |
0.44 |
|
| DMSO |
29.5 |
93.57 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
315.41
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
Kokel D, Cheung CY, Mills R, Coutinho-Budd J, Huang L, Setola V, Sprague J, Jin S, Jin YN, Huang XP, Bruni G, Woolf CJ, Roth BL, Hamblin MR, Zylka MJ, Milan DJ, Peterson RT. Photochemical activation of TRPA1 channels in neurons and animals. Nat Chem Biol. 2013 Apr;9(4):257-63. doi: 10.1038/nchembio.1183. Epub 2013 Feb 10. PMID: 23396078; PMCID: PMC3604056.
In vitro protocol:
Kokel D, Cheung CY, Mills R, Coutinho-Budd J, Huang L, Setola V, Sprague J, Jin S, Jin YN, Huang XP, Bruni G, Woolf CJ, Roth BL, Hamblin MR, Zylka MJ, Milan DJ, Peterson RT. Photochemical activation of TRPA1 channels in neurons and animals. Nat Chem Biol. 2013 Apr;9(4):257-63. doi: 10.1038/nchembio.1183. Epub 2013 Feb 10. PMID: 23396078; PMCID: PMC3604056.
In vivo protocol:
Kokel D, Cheung CY, Mills R, Coutinho-Budd J, Huang L, Setola V, Sprague J, Jin S, Jin YN, Huang XP, Bruni G, Woolf CJ, Roth BL, Hamblin MR, Zylka MJ, Milan DJ, Peterson RT. Photochemical activation of TRPA1 channels in neurons and animals. Nat Chem Biol. 2013 Apr;9(4):257-63. doi: 10.1038/nchembio.1183. Epub 2013 Feb 10. PMID: 23396078; PMCID: PMC3604056.
1: Lam PY, Mendu SK, Mills RW, Zheng B, Padilla H, Milan DJ, Desai BN, Peterson RT. A high-conductance chemo-optogenetic system based on the vertebrate channel Trpa1b. Sci Rep. 2017 Sep 19;7(1):11839. doi: 10.1038/s41598-017-11791-z. PMID: 28928472; PMCID: PMC5605526.
2: Kheradpezhouh E, Choy JMC, Daria VR, Arabzadeh E. TRPA1 expression and its functional activation in rodent cortex. Open Biol. 2017 Apr;7(4):160314. doi: 10.1098/rsob.160314. PMID: 28424320; PMCID: PMC5413904.
3: Lu Y, Piplani H, McAllister SL, Hurt CM, Gross ER. Transient Receptor Potential Ankyrin 1 Activation within the Cardiac Myocyte Limits Ischemia- reperfusion Injury in Rodents. Anesthesiology. 2016 Dec;125(6):1171-1180. doi: 10.1097/ALN.0000000000001377. PMID: 27748654; PMCID: PMC5110384.
4: Kokel D, Cheung CY, Mills R, Coutinho-Budd J, Huang L, Setola V, Sprague J, Jin S, Jin YN, Huang XP, Bruni G, Woolf CJ, Roth BL, Hamblin MR, Zylka MJ, Milan DJ, Peterson RT. Photochemical activation of TRPA1 channels in neurons and animals. Nat Chem Biol. 2013 Apr;9(4):257-63. doi: 10.1038/nchembio.1183. Epub 2013 Feb 10. PMID: 23396078; PMCID: PMC3604056.
