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SML0127

Sigma-Aldrich

Longdaysin

≥98% (HPLC)

Synonyme(s) :

9-isopropyl-N-(3-(trifluoromethyl)benzyl)-9H-purin-6-amine

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About This Item

Formule empirique (notation de Hill):
C16H16F3N5
Numéro CAS:
1353867-91-0
Poids moléculaire :
335.33
Numéro MDL:
MFCD20527323
Code UNSPSC :
12352200
ID de substance PubChem :
329825177
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to tan

Solubilité

DMSO: ≥15 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

CC(C)N(C=N1)C2=C1C(NCC3=CC(C(F)(F)F)=CC=C3)=NC=N2

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)

Clé InChI

REKSFCCYDQMSIN-UHFFFAOYSA-N

Application

Longdaysin may be used to study cell signaling that regulate the circadian clock and behavior.

Actions biochimiques/physiologiques

Longdaysin inhibits CK1, ERK2, and CDK7 kinases in low mM concentrations. The activity of longdaysin results in a lengthening of circadian periods in cell based and in vivo systems. Transgenic zebrafish harboring a per3-luc reporter gene displayed a 10 hour lengthening of circadian period when treated with longdaysin. Longdaysin reduces the phosphorylation of PER1 the regulator of molecular clock function and manipulates the circadian clock.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H315,H319,H335,H361d

Classification des risques

Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Tsuyoshi Hirota et al.
Science (New York, N.Y.), 337(6098), 1094-1097 (2012-07-17)
Impairment of the circadian clock has been associated with numerous disorders, including metabolic disease. Although small molecules that modulate clock function might offer therapeutic approaches to such diseases, only a few compounds have been identified that selectively target core clock
Urs Albrecht
Handbook of experimental pharmacology, (217)(217), 227-239 (2013-04-23)
Circadian clocks are present in nearly all tissues of an organism, including the brain. The brain is not only the site of the master coordinator of circadian rhythms located in the suprachiasmatic nuclei (SCN) but also contains SCN-independent oscillators that
Cyclic uniaxial mechanical load enhances chondrogenesis through entraining the molecular circadian clock.
V?!g??, et al.
Journal of Pineal Research, 73, e12827-e12827 (2022)
M Abdulhadi Alagha et al.
Cartilage, 13(2_suppl), 53S-67S (2020-02-16)
Circadian rhythms in cartilage homeostasis are hypothesized to temporally segregate and synchronize the activities of chondrocytes to different times of the day, and thus may provide an efficient mechanism by which articular cartilage can recover following physical activity. While the
Tsuyoshi Hirota et al.
PLoS biology, 8(12), e1000559-e1000559 (2010-12-24)
The circadian clock underlies daily rhythms of diverse physiological processes, and alterations in clock function have been linked to numerous pathologies. To apply chemical biology methods to modulate and dissect the clock mechanism with new chemical probes, we performed a
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