MRT199665 - ≥99% , CAS No.1456858-57-3

CAS: 1456858-57-3 Cat. No.: M646396 Molecular Weight: 469.58 PubChem CID: 71725150

GRADE & PURITY ≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

MRT199665 is a potent and ATP-competitive, selective MARK / SIK / AMPK inhibitor with IC 50 s of 2/2/3/2 nM, 10/10 nM, and 110/12/43 nM for MARK1/MARK2/MARK3/MARK14 , AMPKα1/AMPKα2 , and SIK1/SIK2/SIK3 , respectively MRT199665 causes apoptosis in MEF2C-activated human acute myeloid leukemias (AML) cells MRT199665 inhibits the phosphorylation of SIK substrate CRTC3 at S370

In Vitro

MRT199665 (1 μM; pre-treated for 1 h) increases LPS (100 ng/mL; stimulated for up to 24 h)-stimulated IL-10 mRNA and Nurr77 mRNA production, and IL-10 secretion. MRT199665 (1 nM-100 μM; 48 hours) reduces leukemia growth. MRT199665 treatment can block MEF2C S222 phosphorylation in acute myeloid leukemias (AML) cells.\nMRT199665 (10 nM-1000 nM; 12 hours) leads to a dose-dependent reduction in total and pS222 MEF2C. MRT199665 also causes a decrease of total MEF2C protein. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: OCI-AML2 and MOLM-13 cells Concentration: 10, 100, 500, and 1000 nM Incubation Time: 12 hours Result: Led to a dose-dependent reduction in total and pS222 MEF2C, causing more than 40% reduction in MEF2C phosphorylation at 10 nM as compared to untreated cells. Cell Proliferation AssayCell Line: Human AML cell lines OCI-AML2, MV4-11, MOLM-13 and Kasumi-1 with endogenous MEF2C phosphorylation; human AML cell lines NB-4, HEL, HL-60 and U937 lacking MEF2C Concentration: 1 nM, 10 nM, 100n M, 1 μM, 10 μM, 100μM Incubation Time: 48 hours Result: Human AML cell lines with endogenous MEF2C phosphorylation (OCI-AML2, MV4–11, MOLM-13 and Kasumi-1) were more sensitive as compared to cell lines lacking MEF2C (NB-4, HEL, HL-60 and U937), with mean IC 50 of 26±13 versus 990±29 nM, respectively.

Form:Solid

IC50& Target:MARK1 2 nM (IC 50 ) MARK2 2 nM (IC 50 ) MARK3 3 nM (IC 50 ) MARK4 2 nM (IC 50 ) SIK1 110 nM (IC 50 ) SIK2 12 nM (IC 50 ) SIK3 43 nM (IC 50 ) NUAK1 3 nM (IC 50 ) NUAK2 120 nM (IC 50 ) AMPKα1 10 nM (IC 50 ) AMPKα2 10 nM (IC 50 ) MELK 29 nM (IC 50 ) TBK1 5400 nM (IC 50 ) IKKε 7700 nM (IC 50 ) BRSK2 10000 nM (IC 50 )

Specifications

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

MRT199665 is a potent and ATP-competitive, selective MARK / SIK / AMPK inhibitor with IC 50 s of 2/2/3/2 nM, 10/10 nM, and 110/12/43 nM for MARK1/MARK2/MARK3/MARK14 , AMPKα1/AMPKα2 , and SIK1/SIK2/SIK3 , respectively. MRT199665 causes apoptosis in ME

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC1(C2=CN=C(N=C2N(C1=O)C3CCC4=C3C=CC=C4O)NC5=CC=CC(=C5)CN6CCCC6)C
• IUPAC Name: 7-[(1S)-4-hydroxy-2,3-dihydro-1H-inden-1-yl]-5,5-dimethyl-2-[3-(pyrrolidin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-6-one
• InChIKey: OFIFLUFVENTCNZ-QHCPKHFHSA-N
• INCHI: 1S/C28H31N5O2/c1-28(2)22-16-29-27(30-19-8-5-7-18(15-19)17-32-13-3-4-14-32)31-25(22)33(26(28)35)23-12-11-21-20(23)9-6-10-24(21)34/h5-10,15-16,23,34H,3-4,11-14,17H2,1-2H3,(H,29,30,31)/t23-/m0/s1
• Isomeric SMILES: CC1(C2=CN=C(N=C2N(C1=O)[C@H]3CCC4=C3C=CC=C4O)NC5=CC=CC(=C5)CN6CCCC6)C
• PubChem CID: 71725150
• MeSH Entry Terms: MRT199665
• Molecular Weight: 469.58

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolopyrimidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolopyrimidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrrolopyrimidines
• Alternative Parents: Indanes Aniline and substituted anilines Benzylamines Phenylmethylamines Aminopyrimidines and derivatives Aralkylamines 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Imidolactams N-alkylpyrrolidines Heteroaromatic compounds Tertiary carboxylic acid amides Pyrroles Trialkylamines Amino acids and derivatives Lactams Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indane - Pyrrolopyrimidine - Benzylamine - Phenylmethylamine - Aniline or substituted anilines - Aminopyrimidine - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Monocyclic benzene moiety - Imidolactam - Benzenoid - N-alkylpyrrolidine - Pyrimidine - Heteroaromatic compound - Pyrrole - Pyrrolidine - Tertiary carboxylic acid amide - Tertiary aliphatic amine - Lactam - Carboxamide group - Amino acid or derivatives - Tertiary amine - Azacycle - Carboxylic acid derivative - Amine - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• 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

Chemical and Physical Properties

• Solubility: DMSO : 125 mg/mL (266.20 mM; Need ultrasonic)
• Molecular Weight: 469.600 g/mol
• XLogP3: 4.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 469.248 Da
• Monoisotopic Mass: 469.248 Da
• Topological Polar Surface Area: 81.600 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 770.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1