5.05206

Photochromic TrpA1 Channel Activator, Optovin

• Synonym(s): Photochromic TrpA1 Channel Activator, Optovin, (E)-5-((2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl)methylene)-2-thioxothiazolidin-4-one, PDSP 22594, Transient Receptor Potential A1 Ion Channel Activator I, TrpA1 Channel Activator I
• Empirical Formula (Hill Notation): C₁₅H₁₃N₃OS₂
• CAS Number: 348575-88-2
• Molecular Weight: 315.41
• UNSPSC Code: 41106609
• NACRES: NA.77

Properties

• Assay: ≥95% (HPLC)
• Quality Level: 100
• form: powder
• potency: 2 μM EC₅₀
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: yellow
• solubility: DMSO: 100 mg/mL
• storage temp.: 2-8°C

Description

General description

A rhodanine derivative that acts as a reversible, photoactivated (λ_{max = 415 nm), and highly TrpA1-selective channel activator, presumably by a light-activated cysteine alkylation mechanism via the α,β-unsaturated alkene group of Optovin rhodanine moiety, and enables light-induced primary murine DRG calcium response in a TrpA1-dependent and HC-030031- (Cat. No. 648485) blockable manner, allowing light-induced activation only in hTrpA1-expressing, but not TrpV1- or TrpM8-expressing, HEK293T transfectants. Its in vivo efficacy is demonstrated in light-induced zebrafish motor activity (EC50/ECmax = 2 µM/3 µM; with >1.6 µW/min 387-405 nm excitation) and low power 405 nm laser-induced head shake/twitch response in mice (0.3 µmol Optovin/20 uL DMSO/ear applied atopically before laser illumination). Exhibits little or no inhibitory activity toward hERG or a panel of 50 human and rodent CNS receptors, channels, and transporters.}

A rhodanine derivative that acts as a reversible, photoactivated (λ_max = 415 nm), and highly TrpA1-selective channel activator and enables light-induced primary murine DRG calcium response in a TrpA1-dependent and HC-030031- (Cat. No. 648485) blockable manner, allowing light-induced activation only in hTrpA1-expressing, but not TrpV1- or TrpM8-expressing, HEK293T transfectants. Its in vivo efficacy is demonstrated in light-induced zebrafish motor activity (EC₅₀/EC_max = 2 µM/3 µM) and low power 405 nm laser-induced head twitch response in mice (0.3 µmol Optovin/20 uL DMSO/ear applied atopically). Exhibits little or no inhibitory activity toward hERG or a panel of 50 human and rodent CNS receptors, channels, and transporters.

Biochem/physiol Actions

Primary Target
TrpA1

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Other Notes

Kokel, D., et al. 2013, Nat. Chem. Biol.9, 257.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable