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Key Documents

5.09267

Sigma-Aldrich

Opn4 Antagonist

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:
Molecular Weight:
269.36
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

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

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

General description

A sulfonamide compound that prevents melanopsin/Opn4 photoactivation in a reversible and cis-Retinal-competitive manner (Kb = 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.
A sulfonamide compound that prevents melanopsin/Opn4 photoactivation in a reversible and cis-Retinal-competitive manner 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 (IC50 = 665 nM; using CHO transfectants), murine Opn4 (IC50 = 190 nM; using transfected Xenopus oocytes), and rat Opn4 (10 µM; using primary rat ipRGCs). Shown to effectively suppress PLR (pupillary light reflex; pupil constriction) in a time- and Opn4-dependent manner in mice (30 mg/kg i.p.) 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 Ki: 110 and 160 nM for human and mouse melanopsin, respectively)

Packaging

Packaged under inert gas

Warning

Toxicity: Regulatory Review (Z)

Reconstitution

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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