Optovin | CAS#348575-88-2 | photoactive TRPA1 activator

Optovin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522715

CAS#: 348575-88-2

Description: Optovin is a photoactive TRPA1 activator. Optovin activates human TRPA1 via structure-dependent photochemical reactions with redox-sensitive cysteine residues. In animals with severed spinal cords, optovin treatment enables control of motor activity in the paralyzed extremities by localized illumination. These studies identify a light-based strategy for controlling endogenous TRPA1 receptors in vivo, with potential clinical and research applications in nontransgenic animals, including humans.

Chemical Structure

Optovin

CAS# 348575-88-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 522715
Name: Optovin
CAS#: 348575-88-2
Chemical Formula: C15H13N3OS2
Exact Mass: 315.05
Molecular Weight: 315.409
Elemental Analysis: C, 57.12; H, 4.15; N, 13.32; O, 5.07; S, 20.33

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450
200mg	USD 750
500mg	USD 1450
1g	USD 2250
2g	USD 3850
5g	USD 6450
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Optovin

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

Appearance: Solid powder

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

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Product Data:

Product Data

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	25.0	79.26
	DMF:PBS (pH 7.2) (1:6)	0.1	0.44
	DMSO	29.5	93.57

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.

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1: 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. PubMed PMID: 23396078; PubMed Central PMCID: PMC3604056.

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