Page last updated: 2024-12-09

ucl 1684

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Description

UCL 1684 : A quinolinium ion that is the dication which results from the joining of two molecules of 4-aminoquinolinium via a 1,3-dimethylbenzene linker at positions 1 and 4, thus forming a cyclic structure. It is a potent blocker of Ca(2+)-activated K(+) channels in rats. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID656733
CHEMBL ID117908
CHEMBL ID1178830
CHEBI ID35040
CHEBI ID291797
SCHEMBL ID16776721
MeSH IDM0286093

Synonyms (20)

Synonym
1$l^{5},9$l^{5},17,24-tetraazaheptacyclo[23.6.2.2^{9,16}.2^{19,22}.1^{3,7}.0^{10,15}.0^{26,31}]octatriaconta-1(31),3(38),4,6,9,11,13,15,19,21,25,27,29,32,34,36-hexadecaene-1,9-bis(ylium)
gtpl2320
ucl 1684
ucl1684
6,10-diaza-3(1,3)8,(1,4)-dibenzena-1,5(1,4)-diquinolinacyclodecaphane
ucl-1684
CHEMBL117908 ,
chebi:35040 ,
17,25-diazonia-2,9-diazaheptacyclo[23.6.2.24,7.210,17.119,23.011,16.026,31]octatriaconta-1(31),4,6,10(35),11,13,15,17(34),19,21,23(38),25,27,29,32,36-hexadecaene
17,25-diazonia-2,9-diazaheptacyclo[23.6.2.24,7.210,17.119,23.011,16.026,31]octatriaconta-1(32),4,6,10(35),11(16),12,14,17(34),19,21,23(38),25(33),26(31),27,29,36-hexadecaene
bdbm50061977
AC1LCVHW ,
CHEMBL1178830
chebi:291797
SCHEMBL16776721
17,24-diaza-1,9-diazoniaheptacyclo[23.6.2.29,16.219,22.13,7.010,15.026,31]octatriaconta-1(32),3(38),4,6,9(37),10,12,14,16(36),19,21,25(33),26,28,30,34-hexadecaene
Q27089053
6,10-diaza-1,5(1,4)-diquinolin-1-iuma-3(1,3),8(1,4)-dibenzenacyclodecaphane-11,51-diium
201147-18-4
PD119483
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Small conductance calcium-activated potassium channel protein 2Rattus norvegicus (Norway rat)IC50 (µMol)0.00300.00151.22696.8000AID242705
Small conductance calcium-activated potassium channel protein 3Rattus norvegicus (Norway rat)IC50 (µMol)0.00300.00151.68587.0000AID242705
Small conductance calcium-activated potassium channel protein 3Rattus norvegicus (Norway rat)Ki0.00180.00182.13265.9000AID346945
Small conductance calcium-activated potassium channel protein 1Rattus norvegicus (Norway rat)IC50 (µMol)0.00300.00151.22696.8000AID242705
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amine oxidase [flavin-containing] A Rattus norvegicus (Norway rat)Kd0.00270.00271.66496.4000AID346946
Small conductance calcium-activated potassium channel protein 3Rattus norvegicus (Norway rat)Kd0.00270.00271.66496.4000AID346946
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID1346442Human KCa2.2 (Calcium- and sodium-activated potassium channels)2010Progress in neurobiology, Jul, Volume: 91, Issue:3
Small conductance calcium-activated potassium channels: from structure to function.
AID1346452Human KCa2.3 (Calcium- and sodium-activated potassium channels)2010Progress in neurobiology, Jul, Volume: 91, Issue:3
Small conductance calcium-activated potassium channels: from structure to function.
AID1346438Rat KCa2.2 (Calcium- and sodium-activated potassium channels)2000British journal of pharmacology, Mar, Volume: 129, Issue:5
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.
AID1346449Human KCa2.1 (Calcium- and sodium-activated potassium channels)2000British journal of pharmacology, Mar, Volume: 129, Issue:5
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.
AID1346449Human KCa2.1 (Calcium- and sodium-activated potassium channels)2010Progress in neurobiology, Jul, Volume: 91, Issue:3
Small conductance calcium-activated potassium channels: from structure to function.
AID1346463Rat KCa2.3 (Calcium- and sodium-activated potassium channels)2001The Journal of physiology, Sep-01, Volume: 535, Issue:Pt 2
SK3 is an important component of K(+) channels mediating the afterhyperpolarization in cultured rat SCG neurones.
AID1346452Human KCa2.3 (Calcium- and sodium-activated potassium channels)2001The Journal of biological chemistry, Apr-13, Volume: 276, Issue:15
Calcium-activated potassium channels sustain calcium signaling in T lymphocytes. Selective blockers and manipulated channel expression levels.
AID1346442Human KCa2.2 (Calcium- and sodium-activated potassium channels)2001The Journal of biological chemistry, Apr-13, Volume: 276, Issue:15
Calcium-activated potassium channels sustain calcium signaling in T lymphocytes. Selective blockers and manipulated channel expression levels.
AID346946Inhibition of Wistar rat recombinant SK3 channel expressed in HEK293 cells by whole cell patch clamp technique2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Synthesis and structure-activity relationship studies of 2-(N-substituted)-aminobenzimidazoles as potent negative gating modulators ofsmall conductance Ca2+-activated K+ channels.
AID242705Inhibition of after hyperpolarization (AHP) of cultured rat sympathetic neurons as SKCa channel blocking activity2004Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16
Bis-quinolinium cyclophanes: toward a pharmacophore model for the blockade of apamin-sensitive SKCa channels in sympathetic neurons.
AID19933Equieffective molar ratio is ratio of the concentration of the test compound and dequalinium that cause 50% inhibition of AHP2000Journal of medicinal chemistry, Sep-21, Volume: 43, Issue:19
bis-Quinolinium cyclophanes: 8,14-diaza-1,7(1, 4)-diquinolinacyclotetradecaphane (UCL 1848), a highly potent and selective, nonpeptidic blocker of the apamin-sensitive Ca(2+)-activated K(+) channel.
AID180679The blocking of apamin-sensitive [Ca2+]-activated K+ (SKCa) channel was assessed by the compounds ability to inhibit the after-hyperpolarization in cultured rat superior cervical ganglion neurons2000Journal of medicinal chemistry, Feb-10, Volume: 43, Issue:3
Synthesis, molecular modeling, and pharmacological testing of bis-quinolinium cyclophanes: potent, non-peptidic blockers of the apamin-sensitive Ca(2+)-activated K(+) channel.
AID754046Inhibition of KCa2.3 in Sprague-Dawley rat superior cervical ganglion neurons assessed as inhibition of afterhyperpolarization by electrophysiological assay relative to UCL18482013European journal of medicinal chemistry, May, Volume: 63Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca(2+)-activated K+ channels.
AID289128Ratio of concentration drug to dequalinium to cause 50% inhibition of SKca channel-mediated after-hypepolarization in rat sympathetic neurons2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Synthesis and pharmacological testing of polyaminoquinolines as blockers of the apamin-sensitive Ca2+-activated K+ channel (SK(Ca)).
AID196785The ratio of the conc of compound to dequalinium to cause 50% inhibition of the after hyperpolarization (AHP) in cultured rat sympathetic neurones1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Bis-quinolinium cyclophanes: 6,10-diaza-3(1,3),8(1,4)-dibenzena-1,5(1,4)- diquinolinacyclodecaphane (UCL 1684), the first nanomolar, non-peptidic blocker of the apamin-sensitive Ca(2+)-activated K+ channel.
AID754048Inhibition of KCa2.3 in Sprague-Dawley rat superior cervical ganglion neurons assessed as inhibition of afterhyperpolarization by electrophysiological assay2013European journal of medicinal chemistry, May, Volume: 63Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca(2+)-activated K+ channels.
AID229089The ratio of compound concentrations and dequalinium that cause 50% inhibition of the after-hyperpolarization2000Journal of medicinal chemistry, Feb-10, Volume: 43, Issue:3
Synthesis, molecular modeling, and pharmacological testing of bis-quinolinium cyclophanes: potent, non-peptidic blockers of the apamin-sensitive Ca(2+)-activated K(+) channel.
AID196786Compound was tested for SKCa blocking action by measuring its ability to inhibit after hyperpolarization (AHP) in cultured rat sympathetic neurones1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Bis-quinolinium cyclophanes: 6,10-diaza-3(1,3),8(1,4)-dibenzena-1,5(1,4)- diquinolinacyclodecaphane (UCL 1684), the first nanomolar, non-peptidic blocker of the apamin-sensitive Ca(2+)-activated K+ channel.
AID387523Inhibition of Kca channel2008Bioorganic & medicinal chemistry letters, Oct-01, Volume: 18, Issue:19
Initial SAR studies on apamin-displacing 2-aminothiazole blockers of calcium-activated small conductance potassium channels.
AID180690tested for their ability to inhibit the after- hyperpolarization in cultured rat sympathetic neurons2000Journal of medicinal chemistry, Sep-21, Volume: 43, Issue:19
bis-Quinolinium cyclophanes: 8,14-diaza-1,7(1, 4)-diquinolinacyclotetradecaphane (UCL 1848), a highly potent and selective, nonpeptidic blocker of the apamin-sensitive Ca(2+)-activated K(+) channel.
AID346945Displacement of [I125]apamine from Wistar rat recombinant SK3 channel expressed in HEK293 cells2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Synthesis and structure-activity relationship studies of 2-(N-substituted)-aminobenzimidazoles as potent negative gating modulators ofsmall conductance Ca2+-activated K+ channels.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (8.33)18.2507
2000's9 (75.00)29.6817
2010's2 (16.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.48

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.48 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]