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5.09267

Opn4 Antagonist

Name: Opn4 Antagonist
Brand: MM

Synonym(s):

Opn4 Antagonist, Opn4 Antagonist, Opsinamide, Melanopsin-inhibiting Sulfonamide AA92593, 1-(4-Methoxy-3-methyl-benzenesulfonyl)piperidine, 1-(4-Methoxy-3-methylphenylsulfonyl)piperidine, Melanopsin Antagonist, Opsinamide AA92593

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About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₉NO₃S

CAS Number:

457961-34-1

Molecular Weight:

269.36

MDL number:

MFCD02227966

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

solid

Storage condition:

OK to freeze, protect from light

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Properties

assay

≥98% (HPLC)

Quality Segment

100

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

white

solubility

DMSO: 100 mg/mL

storage temp.

2-8°C

SMILES string

[S](=O)(=O)(N2CCCCC2)c1cc(c(cc1)OC)C

InChI

1S/C13H19NO3S/c1-11-10-12(6-7-13(11)17-2)18(15,16)14-8-4-3-5-9-14/h6-7,10H,3-5,8-9H2,1-2H3

InChI key

HDTKLZINZGEPFG-UHFFFAOYSA-N

Description

General description

A sulfonamide compound that prevents melanopsin/Opn4 photoactivation in a reversible and cis-Retinal-competitive manner (K_b = 6 and 0.16 µM in competitive binding studies using Opn4 pre-bound with cis-Retinal or not) without apparent affinity toward bovine retina rhodopsin or a panel of 74 other receptors, ion channels, and enzymes. Effectively inhibits cellular phototransduction mediated by human Opn4 in CHO transfectants (IC₅₀ = 665 nM; drug added 30 min before 10 µM 9-cis-Retinal & photoactivation), by murine Opn4 in transfected Xenopus oocytes (IC₅₀ = 190 nM; drug added 3 min before 50 µM 11-cis-Retinal and photoactivation), as well as by endogenous Opn4 in primary rat ipRGCs (intrinsically photosensitive retinal ganglion cells; 10 µM). Shown to be bioavailable in mice via i.p. injection (retina [AA92593] ~7.5 µM 30 min post 30 mg/kg i.p. dosing; >95% clearance within 2 h) and effectively suppress PLR (pupillary light reflex; pupil constriction) in a time- and Opn4-dependent manner in mice in vivo. Likewise, blue light insensitivity is observed in Opn4^-/- and AA92593-treated wild-type, but not vehicle-treated wild-type, P14 neonatal mice.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
melanopsin (Opn4)

Reversible: yes

Target K_i: 110 and 160 nM for human and mouse melanopsin, respectively)

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 monthst at -20°C.

Other Notes

Jones, K.A., et al. 2013. Nat. Chem. Biol.9, 630.

Legal Information

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

Disclaimer

Toxicity: Regulatory Review (Z)

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c