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D7443

Sigma-Aldrich

DPO-1

needles, >97% (NMR)

Synonym(s):

(+)-Neomenthyl diphenylphosphine oxide, (1S,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl]diphenyl-phosphine oxide

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About This Item

Empirical Formula (Hill Notation):
C22H29OP
CAS Number:
43077-30-1
Molecular Weight:
340.44
MDL number:
MFCD09038567
UNSPSC Code:
12352200
PubChem Substance ID:
329798851
NACRES:
NA.77

Assay

>97% (NMR)

form

needles

storage condition

protect from light

color

white

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1P(=O)(c2ccccc2)c3ccccc3

InChI

1S/C22H29OP/c1-17(2)21-15-14-18(3)16-22(21)24(23,19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22+/m1/s1

InChI key

BPCNGVCAHAIZEE-COPCDDAFSA-N

Biochem/physiol Actions

DPO-1 is an inhibitor of human Kv1.5 potassium channel; representative blocker of a novel pharmacophore. The Kv1.5 potassium channel, which underlies the ultrarapid delayed rectifier current, IKur, is reported to be enriched in human atrium versus ventricle, and has been proposed as a target for novel atrial antiarrhythmic therapy. The administration of the IKur blocker (2-isopropyl-5-methyl-cyclohexyl) diphenylphosphine oxide (DPO-1) increases myocardial refractoriness in both atrium and ventricle of rat, but produces an atrial-selective increase in refractoriness in primates; appears to be 15-fold more selective for Kv1.5 vs Kv3.1 channels expressed in Xenopus oocytes. IC50 = 0.16-0.76 μM at 0.1 Hz pulsing frequency; Kd = 0.6 μM.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000037822
0000031357
BGBC0432
093M4701V
047K46212

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Olga Zavaritskaya et al.
British journal of pharmacology, 177(5), 1164-1186 (2019-10-29)
BK channels play important roles in various physiological and pathophysiological processes and thus have been the target of several drug development programmes focused on creating new efficacious BK channel openers, such as the GoSlo-SR compounds. However, the effect of GoSlo-SR
Ning Zhao et al.
PloS one, 8(5), e64629-e64629 (2013-05-30)
Diphenyl phosphine oxide-1 (DPO-1) is a potent Kv1.5 channel inhibitor that has therapeutic potential for the treatment of atrial fibrillation. Many other Kv1.5 channel blockers also potently inhibit the Kv1.3 channel, but whether DPO-1 blocks Kv1.3 channels has not been
Anastasia A Shvetsova et al.
British journal of pharmacology, 177(22), 5148-5162 (2020-08-30)
The vasomotor role of K2P potassium channels during early postnatal development has never been investigated. We tested the hypothesis that TASK-1 channel (K2P family member) contribution to arterial vascular tone and BP is higher in the early postnatal period than
Hongliang Li et al.
European journal of pharmacology, 849, 59-66 (2019-02-05)
In the present study, we investigated the inhibitory effect of tacrolimus, a macrolide immunosuppressive drug that acts through calcineurin inhibition, on voltage-gated K+ (Kv) channels expressed in native smooth muscle cells isolated from the coronary arteries of rabbits. Tacrolimus reduced
Jonas Streit et al.
Scientific reports, 8(1), 1153-1153 (2018-01-20)
Voltage-gated ion channels (VGCs) are prime targets for the pharmaceutical industry, but drug profiling on VGCs is challenging, since drug interactions are confined to specific conformational channel states mediated by changes in transmembrane potential. Here we combined various optogenetic tools
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