MedKoo Cat#: 526799 | Name: KU14R

Description:

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

KU14R is an imidazoline I(3) receptor antagonist. KU14R selectively blocks the insulin secretory response to imidazolines. KU14R has been shown to block the effects of the atypical I(3) agonist efaroxan at the level of the ATP-sensitive K(+) (K(ATP)) channel in isolated pancreatic islet beta cells. KU14R does not act as an antagonist of either efaroxan or S22068 at an imidazoline site in vivo. Imidazolines are a class of investigational antidiabetic drugs.

Chemical Structure

KU14R
KU14R
CAS#189224-48-4

Theoretical Analysis

MedKoo Cat#: 526799

Name: KU14R

CAS#: 189224-48-4

Chemical Formula: C13H14N2O

Exact Mass: 214.1106

Molecular Weight: 214.27

Elemental Analysis: C, 72.87; H, 6.59; N, 13.07; O, 7.47

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Synonym
KU14R; KU-14R; KU 14R.
IUPAC/Chemical Name
2-(2-ethyl-3H-1-benzofuran-2-yl)-1H-imidazole
InChi Key
JCWVNNMJXQJVNC-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H14N2O/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13/h3-8H,2,9H2,1H3,(H,14,15)
SMILES Code
CCC1(C2=NC=CN2)OC3=C(C=CC=C3)C1
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
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
More Info
Product Data
Biological target:
KU14R is a new I(3)-R antagonist, which selectively blocks the insulin secretory response to imidazolines.
In vitro activity:
Stimulation of insulin secretion by harmane was attenuated by the imidazoline I(3) receptor antagonist KU14R (2 (2-ethyl 2,3-dihydro-2-benzofuranyl)-2-imidazole) and was reduced when islets were treated with efaroxan for 18 h, prior to the addition of harmane. Reference: Eur J Pharmacol. 2003 Dec 15;482(1-3):189-96. https://pubmed.ncbi.nlm.nih.gov/14660022/
In vivo activity:
Additionally, KU14R dose-dependently inhibited the morin-induced effects, including hypoglycemia and the increase in insulin secretion and plasma C-peptide levels, in diabetic rats. Furthermore, morin enhanced insulin secretion from isolated pancreatic islets, and this effect was also dose-dependently inhibited by KU14R. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2017 Oct;390(10):997-1003. https://pubmed.ncbi.nlm.nih.gov/28689255/

Preparing Stock Solutions

The following data is based on the product molecular weight 214.27 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.

Recalculate based on batch purity %
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:
1. Li T, Wang Y, Huang S, Tang H. The Regulation Mechanism of MUC5AC Secretion in Airway of Obese Asthma. Cell Mol Biol (Noisy-le-grand). 2022 Jul 31;68(7):153-159. doi: 10.14715/cmb/2022.68.7.25. PMID: 36495503. 2. Cooper EJ, Hudson AL, Parker CA, Morgan NG. Effects of the beta-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans. Eur J Pharmacol. 2003 Dec 15;482(1-3):189-96. doi: 10.1016/j.ejphar.2003.09.039. PMID: 14660022. 3. Lin MH, Hsu CC, Lin J, Cheng JT, Wu MC. Identification of morin as an agonist of imidazoline I-3 receptor for insulin secretion in diabetic rats. Naunyn Schmiedebergs Arch Pharmacol. 2017 Oct;390(10):997-1003. doi: 10.1007/s00210-017-1399-7. Epub 2017 Jul 8. PMID: 28689255. 4. Bozdagi O, Wang XB, Martinelli GP, Prell G, Friedrich VL Jr, Huntley GW, Holstein GR. Imidazoleacetic acid-ribotide induces depression of synaptic responses in hippocampus through activation of imidazoline receptors. J Neurophysiol. 2011 Mar;105(3):1266-75. doi: 10.1152/jn.00263.2010. Epub 2011 Jan 12. PMID: 21228308; PMCID: PMC3074409.
In vitro protocol:
1. Li T, Wang Y, Huang S, Tang H. The Regulation Mechanism of MUC5AC Secretion in Airway of Obese Asthma. Cell Mol Biol (Noisy-le-grand). 2022 Jul 31;68(7):153-159. doi: 10.14715/cmb/2022.68.7.25. PMID: 36495503. 2. Cooper EJ, Hudson AL, Parker CA, Morgan NG. Effects of the beta-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans. Eur J Pharmacol. 2003 Dec 15;482(1-3):189-96. doi: 10.1016/j.ejphar.2003.09.039. PMID: 14660022.
In vivo protocol:
1. Lin MH, Hsu CC, Lin J, Cheng JT, Wu MC. Identification of morin as an agonist of imidazoline I-3 receptor for insulin secretion in diabetic rats. Naunyn Schmiedebergs Arch Pharmacol. 2017 Oct;390(10):997-1003. doi: 10.1007/s00210-017-1399-7. Epub 2017 Jul 8. PMID: 28689255. 2. Bozdagi O, Wang XB, Martinelli GP, Prell G, Friedrich VL Jr, Huntley GW, Holstein GR. Imidazoleacetic acid-ribotide induces depression of synaptic responses in hippocampus through activation of imidazoline receptors. J Neurophysiol. 2011 Mar;105(3):1266-75. doi: 10.1152/jn.00263.2010. Epub 2011 Jan 12. PMID: 21228308; PMCID: PMC3074409.
1: Bleck C, Wienbergen A, Rustenbeck I. Essential role of the imidazoline moiety in the insulinotropic effect but not the KATP channel-blocking effect of imidazolines; a comparison of the effects of efaroxan and its imidazole analogue, KU14R. Diabetologia. 2005 Dec;48(12):2567-75. Epub 2005 Nov 11. PubMed PMID: 16283242. 2: Mayer G, Taberner PV. Effects of the imidazoline ligands efaroxan and KU14R on blood glucose homeostasis in the mouse. Eur J Pharmacol. 2002 Nov 1;454(1):95-102. PubMed PMID: 12409010. 3: Ball AJ, Flatt PR, McClenaghan NH. Stimulation of insulin secretion in clonal BRIN-BD11 cells by the imidazoline derivatives KU14r and RX801080. Pharmacol Res. 2000 Dec;42(6):575-9. PubMed PMID: 11058411.