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U8881

Sigma-Aldrich

UCL 1684 ditrifluoroacetate hydrate

Synonym(s):

6,12,19,20,25,26-hexahydro- 5,27:13,18:21,24-Trietheno-11,7-metheno-7H-dibenzo[b,m][1,5,12,16]tetraazacyclotricosine-5,13-diium ditrifluoroacetate hydrate

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About This Item

Linear Formula:
(C34H30N4)2+ · (C2F3O2-)2 · xH2O
CAS Number:
201147-19-5
Molecular Weight:
720.66 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
24900684
NACRES:
NA.77

color

white to off-white

Quality Level

100

solubility

DMSO: 10 mg/mL

SMILES string

[H]O[H].FC(F)(C(O)=O)F.FC(F)(C(O)=O)F.C12=CC=CC=C1C(NCC3=CC=C(CNC4=CC=[N+](C5)C6=C4C=CC=C6)C=C3)=CC=[N+]2CC7=CC=CC5=C7

InChI

1S/C34H28N4.2C3H3F3O2.H2O/c1-3-10-33-29(8-1)31-16-18-37(33)23-27-6-5-7-28(20-27)24-38-19-17-32(30-9-2-4-11-34(30)38)36-22-26-14-12-25(13-15-26)21-35-31;2*4-3(5,6)1-2(7)8;/h1-20H,21-24H2;2*1H2,(H,7,8);1H2/b35-31+,36-32+;;;

InChI key

YROHEYZVNZITJN-DDVHGCDCSA-N

Application

UCL 1684 ditrifluoroacetate hydrate has been used for analyzing the mechanism for ammonium-mediated displacement of the protonated analyte from analyte-trifluoroacetic acid (TFA) ion-pair. UCL 1684 has also been used as a potassium channel inhibitor to study CNP (C-type natriuretic peptide)-induced relaxations in pig coronary arteries.

Biochem/physiol Actions

UCL 1684 is a potent non-peptide blocker of the apamin-sensitive Ca2+-activated K+ channel. It comprises two quinolinium rings and is similar to apamin arginine residue. UCL 1684 inhibits calcium-activated K current (Kslow) and modulates islet β-cell.

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.

Preparation Note

UCL 1684 ditrifluoroacetate hydrate is soluble in water at 10 mg/ml.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Pharmacological properties and functional role of Kslow current in mouse pancreatic beta-cells: SK channels contribute to Kslow tail current and modulate insulin secretion
Zhang M, et al.
The Journal of General Physiology, 126(4), 353-363 (2005)
Crucial role of a shared extracellular loop in apamin sensitivity and maintenance of pore shape of small-conductance calcium-activated potassium (SK) channels
Weatherall KL, et al.
Proceedings of the National Academy of Sciences of the USA, 108(45), 18494-18499 (2011)
Chao Fan Liang et al.
The Journal of pharmacology and experimental therapeutics, 334(1), 223-231 (2010-03-25)
The present experiments investigated whether endothelium-derived mediators modulate the effect of natriuretic peptides in porcine coronary arteries. Rings with and without endothelium were suspended in organ chambers for isometric tension recording. Concentration-relaxation curves to C-type natriuretic peptide (CNP) and atrial
P M Dunn
European journal of pharmacology, 368(1), 119-123 (1999-03-30)
The novel K+ channel blocker 6,10-diaza-3(1,3)8,(1,4)-dibenzena-1,5(1,4)-diquinolinacy clodecaphane (UCL 1684) has been tested for its ability to inhibit Ca2+ -activated K+ currents in cultured rat chromaffin cells. Low nanomolar concentrations of UCL 1684 produced a rapid and reversible inhibition of the
F S Michel et al.
British journal of pharmacology, 155(2), 217-226 (2008-06-25)
Experiments were designed to determine the modulation by nitric oxide (NO) and endothelium-dependent hyperpolarizations (EDHF-mediated responses) of endothelium-dependent contractions in renal arteries of normotensive and hypertensive rats. Rings, with or without endothelium, of renal arteries of 8-month-old Wistar Kyoto rats
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