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BioAssay: AID 458181

Thermodynamic aqueous solubility in equal volume of ethyl alcohol and 1/15M phosphate buffer at pH 7.4

The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical more ..
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 Tested Compounds
 Tested Compounds
All(7)
 
 
Unspecified(7)
 
 
 Tested Substances
 Tested Substances
All(7)
 
 
Unspecified(7)
 
 
 Related BioAssays
 Related BioAssays
AID: 458181
Data Source: ChEMBL (609239)
Depositor Category: Literature, Extracted
BioAssay Version:
Deposit Date: 2010-07-30
Modify Date: 2014-05-26

Data Table ( Complete ):           View All Data
Tested Compounds:
Description:
Title: beta-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: improvement of solubility by disruption of molecular planarity.

Abstract: The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did beta-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules.
(PMID: 20060304)
Comment
Putative Target:
ChEMBL Target ID: 22229
Target Type: NO TARGET
Pref Name: No relevant target
Confidence: Default value - Target unknown or has yet to be assigned
Relationship Type: Default value - Target has yet to be curated
Categorized Comment - additional comments and annotations
From ChEMBL:
Assay Type: Physicochemical
Assay Data Source: Scientific Literature
BAO: Assay Format: small-molecule physicochemical format
Result Definitions
TIDNameDescriptionHistogramTypeUnit
OutcomeThe BioAssay activity outcomeOutcome
1Solubility activity commentSolubility activity commentString
2Solubility standard flagSolubility standard flagInteger
3Solubility qualifierSolubility qualifierString
4Solubility published valueSolubility published valueFloatug ml-1
5Solubility standard valueSolubility standard valueFloatug.mL-1

Data Table (Concise)
Data Table ( Complete ):     View All Data
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