SR9011 - Moligand™, ≥98% , CAS No.1379686-29-9

CAS: 1379686-29-9 Cat. No.: S648031 Summenformel: C₂₃H₃₁ClN₄O₃S Molekulargewicht: 479.04 EG-Nummer: 111-075-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

3-(((4-Chlorobenzyl)((5-nitrothiophen-2-yl)methyl)amino)methyl)-N-pentylpyrrolidine-1-carboxamide | SR9011 | SR-9011 | UNII-VYI79FLZ6W | 1-Pyrrolidinecarboxamide, 3-((((4-chlorophenyl)methyl)((5-nitro-2-thienyl)methyl)amino)methyl)-n-pentyl- | GTPL8900 |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

SR9011 is a REV-ERBα / β agonist with IC 50 s of 790 nM and 560 nM for REV-ERBα and REV-ERBβ, respectively.

In Vitro

SR9011 dose-dependently increases the REV-ERB-dependent repressor activity assessed in HEK293 cells expressing a chimeric Gal4 DNA Binding Domain (DBD) - REV-ERB ligand binding domain (LBD) α or β and a Gal4-responsive luciferase reporter (REV-ERBα IC 50 =790 nM, REV-ERBβ IC 50 =560 nM). SR9011 potently and efficaciously suppresses transcription in a cotransfection assay using full-length REV-ERBα along with a luciferase reporter driven by the Bmal1 promoter (SR9011 IC 50 =620 nM). SR9011 suppresses the expression ofBMAL1 mRNA in HepG2 cells in a REV-ERBα/β -dependent mannerSR9011 suppresses proliferation of the breast cancer cell lines regardless of their ER or HER2 status. SR9011 appears to pause the cell cycle of the breast cancer cells prior to M phase. Cyclin A ( CCNA2 ) is identified as a direct target gene of REV-ERB suggesting that suppression of expression of this cyclin by SR9011 may mediate the cell cycle arrest. Treatment with SR9011 results in an increase in cells in the G 0 /G 1 phase and a decrease of cells in S and G 2 /M phase suggesting that activation of REV-ERB may be resulting in decreased transition from G 1 to S phase and/or from S to G 2 /M phase. 

In Vivo

SR9011 displays reasonable plasma exposure, thus, the expression of REV-ERB responsive genes is examined in the liver of mice treated with various doses of SR9011 for 6-days. The plasminogen activator inhibitor type 1 gene ( Serpine1 ) is a REV-ERB target gene and displays dose-dependent suppression of expression in response to SR9011. The cholesterol 7α-hydroxylase ( Cyp7a1 ) and sterol response element binding protein ( Srepf1 ) genes have also been shown to be responsive to REV-ERB and are dose-dependently suppressed with increasing amounts of SR9011. After 12 days in D:D conditions mice are injected with a single dose of SR9011 or vehicle at CT6 (peak expression of Rev-erbα ). Vehicle injection causes no disruption in circadian locomotor activity. However, administration of a single dose of SR9011 results in loss of locomotor activity during the subject dark phase. Normal activity returns the next circadian cycle, consistent with clearance of the drugs in less than 24h. The SR9011-dependent decrease in wheel running behavior in the mice under constant darkness conditions is dose-dependent and that the potency (ED 50 =56 mg/kg) is similar to the potency of SR9011-mediated suppression of a REV-ERB responsive gene, Srebf1 , in vivo (ED 50 =67mg/kg) . 

Cell Assay

MCF10A, MDA-MB-231, MCF-7, MDA-MB-361, SKBR3, BT474 cells are plated in 6-well plates one day before treatment. The MTT cell proliferation assays are performed. Briefly, 3×10 3 to 5 × 10 3 cells per well are plated in 96-well plates. Twenty-four hours later, cells are treated with SR9011 (0, 2, 4, 6, 8 and 10 μM) or DMSO. Seventy-two hours after treatment, the cells are labeled with 1.2 mM MTT and incubated for 4 hours. DMSO is then added and readings are taken on a plate reader at 540 nm.

Form:Solid

IC50& Target:IC50: 790 nM (Rev-ErbBα), 560 nM (Rev-ErbBβ)

Specifications

Synonyme

3-(((4-Chlorobenzyl)((5-nitrothiophen-2-yl)methyl)amino)methyl)-N-pentylpyrrolidine-1-carboxamide | SR9011 | SR-9011 | UNII-VYI79FLZ6W | 1-Pyrrolidinecarboxamide, 3-((((4-chlorophenyl)methyl)((5-nitro-2-thienyl)methyl)amino)methyl)-n-pentyl- | GTPL8900 |

Spezifikationen & Reinheit

Moligand™, ≥98%

Biochemische und physiologische Mechanismen

SR9011 is a REV-ERBα / β agonist with IC 50 s of 790 nM and 560 nM for REV-ERBα and REV-ERBβ, respectively.

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Note

Moligand™

Reinheit

≥98%

Namen und Kennungen

• Kanonisches Lächeln: CCCCCNC(=O)N1CCC(C1)CN(CC2=CC=C(C=C2)Cl)CC3=CC=C(S3)[N+](=O)[O-]
• IUPAC Name: 3-[[(4-chlorophenyl)methyl-[(5-nitrothiophen-2-yl)methyl]amino]methyl]-N-pentylpyrrolidine-1-carboxamide
• InChIKey: PPUYOYQTTWJTIU-UHFFFAOYSA-N
• INCHI: 1S/C23H31ClN4O3S/c1-2-3-4-12-25-23(29)27-13-11-19(16-27)15-26(14-18-5-7-20(24)8-6-18)17-21-9-10-22(32-21)28(30)31/h5-10,19H,2-4,11-17H2,1H3,(H,25,29)
• Isomere SMILES: CCCCCNC(=O)N1CCC(C1)CN(CC2=CC=C(C=C2)Cl)CC3=CC=C(S3)[N+](=O)[O-]
• Alternative CAS-Nummer: 2070014-94-5
• Molekulargewicht: 479.04

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Thiophenes
      • Subclass Nitrothiophenes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Thiophenes
• Subclass: Nitrothiophenes
• Intermediate Tree Nodes: Not available
• Direct Parent: 2-nitrothiophenes
• Alternative Parents: Pyrrolidinecarboxamides Phenylmethylamines Nitroaromatic compounds Benzylamines 2,5-disubstituted thiophenes Aralkylamines Chlorobenzenes Aryl chlorides Heteroaromatic compounds Ureas Trialkylamines Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organic salts Organic zwitterions Organochlorides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-nitrothiophene - Nitroaromatic compound - Benzylamine - Phenylmethylamine - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine-1-carboxamide - Chlorobenzene - Halobenzene - Aralkylamine - 2,5-disubstituted thiophene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Pyrrolidine - Organic nitro compound - C-nitro compound - Tertiary amine - Tertiary aliphatic amine - Urea - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Allyl-type 1,3-dipolar organic compound - Azacycle - Organic oxoazanium - Organic zwitterion - Organochloride - Organonitrogen compound - Organohalogen compound - Amine - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic salt - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as 2-nitrothiophenes. These are aromatic heterocyclic compound containing a nitro group attached to a thiophene ring a the 2-position.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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NR1D1 Tchem Nuclear receptor subfamily 1 group D member 1 (0 Activities)

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ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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NR3C2 Tclin Mineralocorticoid receptor (2134 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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RARA Tclin Retinoic acid receptor alpha (1324 Activities)

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THRA Tclin Thyroid hormone receptor alpha (894 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)

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ESR2 Tclin Estrogen receptor beta (9272 Activities)

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RARG Tclin Retinoic acid receptor gamma (1154 Activities)

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RXRG Tclin Retinoid X receptor gamma (646 Activities)

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RARB Tclin Retinoic acid receptor beta (1232 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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RXRB Tclin Retinoid X receptor beta (726 Activities)

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ESRRA Tchem Estrogen-related receptor alpha (573 Activities)

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GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

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CSNK1D Tchem Casein kinase I delta (4546 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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ESRRB Tchem Estrogen-related receptor beta (173 Activities)

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ESRRG Tchem Estrogen-related receptor gamma (587 Activities)

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NR1H3 Tchem LXR-alpha (2891 Activities)

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CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

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NR1I2 Tchem Pregnane X receptor (6667 Activities)

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AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

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NR1H2 Tchem LXR-beta (3841 Activities)

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U2OS (164939 Activities)

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NR2E3 Tchem Photoreceptor-specific nuclear receptor (502 Activities)

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NR5A2 Tchem Orphan nuclear receptor LRH-1 (736 Activities)

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NR5A1 Tchem Steroidogenic factor 1 (399 Activities)

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NR1I3 Tchem Nuclear receptor subfamily 1 group I member 3 (655 Activities)

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NR0B2 Tchem Nuclear receptor subfamily 0 group B member 2 (24 Activities)

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HNF4A Tchem Hepatocyte nuclear factor 4-alpha (301 Activities)

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NR4A2 Tchem Nuclear receptor subfamily 4 group A member 2 (460 Activities)

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NR2C2 Tchem Nuclear receptor subfamily 2 group C member 2 (42 Activities)

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RORA Tchem Nuclear receptor ROR-alpha (562 Activities)

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BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

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NR4A1 Tchem Nuclear receptor subfamily 4 group A member 1 (458 Activities)

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NR0B1 Tbio Nuclear receptor subfamily 0 group B member 1 (493 Activities)

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NR1D1 Tchem Nuclear receptor subfamily 1 group D member 1 (332 Activities)

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NR1D2 Tchem Nuclear receptor subfamily 1 group D member 2 (13 Activities)

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PTPRU Tbio Receptor-type tyrosine-protein phosphatase U (2 Activities)

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HNF4G Tbio Hepatocyte nuclear factor 4-gamma (2 Activities)

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NR2C1 Tbio Nuclear receptor subfamily 2 group C member 1 (2 Activities)

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NR2E1 Tbio Nuclear receptor subfamily 2 group E member 1 (116 Activities)

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NR2F1 Tbio COUP transcription factor 1 (7 Activities)

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NR2F2 Tchem COUP transcription factor 2 (234 Activities)

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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Löslichkeit: DMSO : ≥ 43 mg/mL (89.76 mM)
• Molekulargewicht: 479.000 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 478.181 Da
• Monoisotopic Mass: 478.181 Da
• Topological Polar Surface Area: 110.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 600.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1