IUPAC/Chemical Name
9-Isopropyl-N-(3-(trifluoromethyl)benzyl)-9H-purin-6-amine
InChi Key
REKSFCCYDQMSIN-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H16F3N5/c1-10(2)24-9-23-13-14(21-8-22-15(13)24)20-7-11-4-3-5-12(6-11)16(17,18)19/h3-6,8-10H,7H2,1-2H3,(H,20,21,22)
SMILES Code
FC(C1=CC(CNC2=C3N=CN(C(C)C)C3=NC=N2)=CC=C1)(F)F
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
Biological target:
Longdaysin is an inhibitor of the Wnt/β-catenin signaling pathway, which exerts antitumor effect through blocking CK1δ/ε-dependent Wnt signaling.
In vitro activity:
Longdaysin was amenable for chemical modification to perform affinity chromatography coupled with mass spectrometry analysis to identify target proteins. This study characterized the role of CKIα in the clock mechanism and found that CKIα-mediated phosphorylation stimulated degradation of a clock protein PER1, similar to the function of CKIδ. Longdaysin treatment inhibited PER1 degradation, providing insight into the mechanism of longdaysin-dependent period lengthening.
Reference: PLoS Biol. 2010 Dec 14;8(12):e1000559. https://pubmed.ncbi.nlm.nih.gov/21179498/
In vivo activity:
The in vivo antitumor effect of longdaysin was evaluated using MDA-MB-231 breast cancer mouse xenografts. In MDA-MB-231 breast cancer xenografts, treatment with longdaysin suppressed tumor growth in association with inhibition of Wnt/β-catenin signaling.
Reference: Onco Targets Ther. 2019 Feb 5;12:993-1005. https://pubmed.ncbi.nlm.nih.gov/30787621/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
96.0 |
286.28 |
| Ethanol |
67.0 |
199.80 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
335.33
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.
| 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. Xiong Y, Zhou L, Su Z, Song J, Sun Q, Liu SS, Xia Y, Wang Z, Lu D. Longdaysin inhibits Wnt/β-catenin signaling and exhibits antitumor activity against breast cancer. Onco Targets Ther. 2019 Feb 5;12:993-1005. doi: 10.2147/OTT.S193024. PMID: 30787621; PMCID: PMC6368421.
2. Hirota T, Lee JW, Lewis WG, Zhang EE, Breton G, Liu X, Garcia M, Peters EC, Etchegaray JP, Traver D, Schultz PG, Kay SA. High-throughput chemical screen identifies a novel potent modulator of cellular circadian rhythms and reveals CKIα as a clock regulatory kinase. PLoS Biol. 2010 Dec 14;8(12):e1000559. doi: 10.1371/journal.pbio.1000559. PMID: 21179498; PMCID: PMC3001897.
In vitro protocol:
1. Xiong Y, Zhou L, Su Z, Song J, Sun Q, Liu SS, Xia Y, Wang Z, Lu D. Longdaysin inhibits Wnt/β-catenin signaling and exhibits antitumor activity against breast cancer. Onco Targets Ther. 2019 Feb 5;12:993-1005. doi: 10.2147/OTT.S193024. PMID: 30787621; PMCID: PMC6368421.
2. Hirota T, Lee JW, Lewis WG, Zhang EE, Breton G, Liu X, Garcia M, Peters EC, Etchegaray JP, Traver D, Schultz PG, Kay SA. High-throughput chemical screen identifies a novel potent modulator of cellular circadian rhythms and reveals CKIα as a clock regulatory kinase. PLoS Biol. 2010 Dec 14;8(12):e1000559. doi: 10.1371/journal.pbio.1000559. PMID: 21179498; PMCID: PMC3001897.
In vivo protocol:
1. Xiong Y, Zhou L, Su Z, Song J, Sun Q, Liu SS, Xia Y, Wang Z, Lu D. Longdaysin inhibits Wnt/β-catenin signaling and exhibits antitumor activity against breast cancer. Onco Targets Ther. 2019 Feb 5;12:993-1005. doi: 10.2147/OTT.S193024. PMID: 30787621; PMCID: PMC6368421.
2. Hirota T, Lee JW, Lewis WG, Zhang EE, Breton G, Liu X, Garcia M, Peters EC, Etchegaray JP, Traver D, Schultz PG, Kay SA. High-throughput chemical screen identifies a novel potent modulator of cellular circadian rhythms and reveals CKIα as a clock regulatory kinase. PLoS Biol. 2010 Dec 14;8(12):e1000559. doi: 10.1371/journal.pbio.1000559. PMID: 21179498; PMCID: PMC3001897.
1: Kopp R, Martínez IO, Legradi J, Legler J. Exposure to endocrine disrupting chemicals perturbs lipid metabolism and circadian rhythms. J Environ Sci (China). 2017 Dec;62:133-137. doi: 10.1016/j.jes.2017.10.013. Epub 2017 Oct 27. PubMed PMID: 29289284.
2: Bieler J, Cannavo R, Gustafson K, Gobet C, Gatfield D, Naef F. Robust synchronization of coupled circadian and cell cycle oscillators in single mammalian cells. Mol Syst Biol. 2014 Jul 15;10:739. doi: 10.15252/msb.20145218. PubMed PMID: 25028488; PubMed Central PMCID: PMC4299496.
3: St John PC, Hirota T, Kay SA, Doyle FJ 3rd. Spatiotemporal separation of PER and CRY posttranslational regulation in the mammalian circadian clock. Proc Natl Acad Sci U S A. 2014 Feb 4;111(5):2040-5. doi: 10.1073/pnas.1323618111. Epub 2014 Jan 21. PubMed PMID: 24449901; PubMed Central PMCID: PMC3918757.
4: Weger M, Weger BD, Diotel N, Rastegar S, Hirota T, Kay SA, Strähle U, Dickmeis T. Real-time in vivo monitoring of circadian E-box enhancer activity: a robust and sensitive zebrafish reporter line for developmental, chemical and neural biology of the circadian clock. Dev Biol. 2013 Aug 15;380(2):259-73. doi: 10.1016/j.ydbio.2013.04.035. Epub 2013 May 9. PubMed PMID: 23665472.
5: Hirota T, Lee JW, Lewis WG, Zhang EE, Breton G, Liu X, Garcia M, Peters EC, Etchegaray JP, Traver D, Schultz PG, Kay SA. High-throughput chemical screen identifies a novel potent modulator of cellular circadian rhythms and reveals CKIα as a clock regulatory kinase. PLoS Biol. 2010 Dec 14;8(12):e1000559. doi: 10.1371/journal.pbio.1000559. PubMed PMID: 21179498; PubMed Central PMCID: PMC3001897.
