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Submit ReviewDC 271
Description: Fluorescent retinoic acid analog; solvochromatic probe
Chemical Name: 4-[2-[1,2,3,4-Tetrahydro-4,4-dimethyl-1-(1-methylethyl)-6-quinolinyl]ethynyl]benzoic acid
Purity: ≥98% (HPLC)
Biological Activity for DC 271
DC 271 is a fluorescent retinoic acid analog (retinoid all-trans-retinoic acid; ATRA) (Kd = 42 nM at cellular retinoid binding protein II (CRABPII)). Solvochromatic probe: fluorescent λex, λem, and quantum yield affected by solvent type. DC 271 can be used in retinoids assays. Activates same genes as endogenous retinoic acid in human keratinocyte cells (HaCaT) when incubated for 72 h at 1 μM. Also elicits cellular responses consistent with those of retinoic acid. Excitation λ = 351, 350, 382 and 378 nm in DMSO, EtOH, DCM and Toluene, respectively; emission λ = 442, 461, 572 and 447 nm in DMSO, EtOH, DCM and Toluene, respectively. Quantum yield = 19.3, 1.14, 71.45, 80.21 % in DMSO, EtOH, DCM and Toluene, respectively.
Technical Data for DC 271
| M. Wt | 347.46 |
| Formula | C23H25NO2 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 198696-03-6 |
| PubChem ID | 22971725 |
| InChI Key | OCMSZODRCJAGHL-UHFFFAOYSA-N |
| Smiles | CC(N1CCC(C)(C2=CC(C#CC3=CC=C(C(O)=O)C=C3)=CC=C12)C)C |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Product Datasheets for DC 271
References for DC 271
References are publications that support the biological activity of the product.
Chisholm et al (2019) Fluorescent retinoic acid analogues as probes for biochemical and intracellular characterization of retinoid signaling pathways. ACS.Chem.Biol. 14 369 PMID: 30707838
Tomlinson et al (2021) Structure-functional relationship of cellular retinoic acid-binding proteins I and II interacting with natural and synthetic ligands. Acta Crystallogr. D Struct. Biol. 77 164 PMID: 33559606
Tomlinson et al (2018) Novel Fluorescence Competition Assay for Retinoic Acid Binding Proteins ACS.Med.Chem.Lett. 9 1297
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Keywords: DC 271, DC 271 supplier, DC271, Fluorescent, retinoic, acid, analogs, analogues, cellular, retinoid, binding, protein, II, CRABPII, solvochromatic, Tretinoin, ATRA, Retinoic, Acid, Receptors, Retinoid, X, Receptor, Acid-related, Orphan, ESCs, and, iPSC, Organoids, Probes, Fatty, Binding, Proteins, 6873, Tocris Bioscience
Citations for DC 271
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Currently there are no citations for DC 271.
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Literature in this Area
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Retinoid Receptors Scientific Review
Written by Alexander Moise, this review summarizes the nature of retinoid receptors, their isotype and isoform variants and modulation of retinoid signaling. Compounds available from Tocris are listed.