TN1 - ≥95% , CAS No.289479-94-3

CAS: 289479-94-3 Cat. No.: T651970 Molecular Weight: 509.60 PubChem CID: 69828124

GRADE & PURITY ≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

TN1 is a potent fetal hemoglobin ( HbF ) inducer.

In Vitro

A high-throughput screen of a large chemical library identifies a 2,6-diamino-substituted purine, TN1, which induces fetal hemoglobin (HbF) more potently than hydroxyurea in KU812 and K562 leukemia cell lines.TN1 increases HbF protein in both leukemic KU812 and K562 cells in a dose-dependent manner. At 100 nM concentration, Western blot analysis indicated that TN1 increased γ-globin expression (2.9- and 3.7-fold increase in KU812 cell and K562 cell, respectively) to higher levels than 50-100 μM HU (1.8- and 1.9-fold increase in KU812 cell and K562 cell, respectively), the first drug approved for the treatment of SCD. The EC 50 value for TN1-mediated HbF induction is approximately three orders of magnitude lower than that of HU (HU: EC 50 =50-100 μM; TN1: EC 50 =100 nM). In addition, TN1 is more potent than a number of previously reported small-molecule HbF inducers including sodium butyrate and other histone deacetylase (HDAC) inhibitors. At the concentrations tested, TN1, as well as hemin and HU, increase γ-globin mRNA transcription (greater than fourfold), indicating that TN1 increases γ-globin levels at both the transcriptional and protein level. The time course of TN1-induced γ-globin mRNA and protein synthesis is measured and both increase after approximately 24 h of treatment. TN1 also induces β-globin mRNA in addition to γ-globin mRNA, similar to hydroxyurea. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:fetal hemoglobin (HbF)

Specifications

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

TN1 is a potent fetal hemoglobin ( HbF ) inducer.

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.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CCN1C=NC2=C(N=C(N=C21)NC3CCC(CC3)O)NC4=CC(=CC=C4)NC(=O)C#CC5=CC=C(C=C5)C
• IUPAC Name: N-[3-[[9-ethyl-2-[(4-hydroxycyclohexyl)amino]purin-6-yl]amino]phenyl]-3-(4-methylphenyl)prop-2-ynamide
• InChIKey: QPFYQTIUHLNNSI-UHFFFAOYSA-N
• INCHI: 1S/C29H31N7O2/c1-3-36-18-30-26-27(34-29(35-28(26)36)33-21-12-14-24(37)15-13-21)32-23-6-4-5-22(17-23)31-25(38)16-11-20-9-7-19(2)8-10-20/h4-10,17-18,21,24,37H,3,12-15H2,1-2H3,(H,31,38)(H2,32,33,34,35)
• Isomeric SMILES: CCN1C=NC2=C(N=C(N=C21)NC3CCC(CC3)O)NC4=CC(=CC=C4)NC(=O)C#CC5=CC=C(C=C5)C
• PubChem CID: 69828124
• Molecular Weight: 509.60

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Imidazopyrimidines
      • Subclass Purines and purine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Imidazopyrimidines
• Subclass: Purines and purine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: 6-aminopurines
• Alternative Parents: Anilides N-arylamides Aniline and substituted anilines Toluenes Secondary alkylarylamines Cyclohexanols Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Heteroaromatic compounds Secondary carboxylic acid amides Cyclic alcohols and derivatives Amino acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 6-aminopurine - Anilide - Aniline or substituted anilines - N-arylamide - Toluene - Secondary aliphatic/aromatic amine - Cyclohexanol - Aminopyrimidine - Imidolactam - Benzenoid - Pyrimidine - N-substituted imidazole - Monocyclic benzene moiety - Heteroaromatic compound - Imidazole - Cyclic alcohol - Azole - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Amino acid or derivatives - Azacycle - Secondary amine - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Amine - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (196.23 mM; Need ultrasonic)
• Molecular Weight: 509.600 g/mol
• XLogP3: 5.000
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 509.254 Da
• Monoisotopic Mass: 509.254 Da
• Topological Polar Surface Area: 117.000 Ų
• Heavy Atom Count: 38
• Formal Charge: 0
• Complexity: 842.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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