Inauhzin - 10mM in DMSO , CAS No.309271-94-1

CAS: 309271-94-1 Cat. No.: I423193 Molecular Weight: 469.58 EC Number: 809-096-6

GRADE & PURITY 10mM in DMSO

Synonyms

AS-16441 | HY-N7436 | inauhzin | s6744 | 1-Phenothiazin-10-yl-2-(9H-1,3,4,9-tetraaza-fluoren-2-ylsufanyl)-butan-1-one (Inauhzin) | AC-35922 | METHIOCARB SULPHONE | UNII-KX47O2O15C | VHUOXERIKQWIJE-UHFFFAOYSA-N | INZ | Oprea1_520286 | 2-((5H-[1,2,4]triazin

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Inauhzin is a cell-permeableSIRT1inhibitor with an IC50 of 0.7-2 μM and reactivatesp53by inhibiting SIRT1 deacetylation activity.

Targets

SIRT1 ; p53

In vitro

Inauhzin (INZ) is a potent p53 activator and mediates p53-dependent cytotoxicity. INZ inhibits cell proliferation by triggering both apoptosis and senescence in p53-containning cells, though it predominantly induces p53-dependent apoptosis. INZ is able to prevent p53 from MDM2-mediated ubiquitylation and proteasomal degradation and protects p53 without either directly inhibiting MDM2 activity towards p53 or interfering with MDMX/MDM2–p53 interaction. INZ induces acetylation of p53, but not tubulin, in cells. Inauhzin is a (sub)micromolar SIRT1i selective over SIRT2/3.

In vivo

Inauhzin (INZ) has good tumour tissue penetration and is able to inhibit tumour growth by inducing p53.

Cell Research(from reference)

Cell lines：human lung cancer H460, A549, H1299, colon cancer HCT116, HT29, osteosarcoma U2OS and SJSA, breast cancer MCF7, ovarian cancer A2780, IGROV1 and SKOV3 and glioma U87 and U373 cells, as well as human embryonic fibroblast WI-38 and normal human 

Concentrations：0-10 μM 

Incubation Time：18 h 

Specifications

Synonyms

AS-16441 | HY-N7436 | inauhzin | s6744 | 1-Phenothiazin-10-yl-2-(9H-1, 3, 4, 9-tetraaza-fluoren-2-ylsufanyl)-butan-1-one (Inauhzin) | AC-35922 | METHIOCARB SULPHONE | UNII-KX47O2O15C | VHUOXERIKQWIJE-UHFFFAOYSA-N | INZ | Oprea1_520286 | 2-((5H-[1, 2, 4]triazin

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Inauhzin is a cell-permeable SIRT1 inhibitor with an IC50 of 0.7-2 μM and reactivates p53 by inhibiting SIRT1 deacetylation activity.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: CCC(C(=O)N1C2=CC=CC=C2SC3=CC=CC=C31)SC4=NC5=C(C6=CC=CC=C6N5)N=N4
• IUPAC Name: 1-phenothiazin-10-yl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)butan-1-one
• InChIKey: VHUOXERIKQWIJE-UHFFFAOYSA-N
• INCHI: 1S/C25H19N5OS2/c1-2-19(33-25-27-23-22(28-29-25)15-9-3-4-10-16(15)26-23)24(31)30-17-11-5-7-13-20(17)32-21-14-8-6-12-18(21)30/h3-14,19H,2H2,1H3,(H,26,27,29)
• Isomeric SMILES: CCC(C(=O)N1C2=CC=CC=C2SC3=CC=CC=C31)SC4=NC5=C(C6=CC=CC=C6N5)N=N4
• WGK Germany: 3
• Molecular Weight: 469.58
• Reaxy-Rn: 28301495
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=28301495&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzothiazines
      • Subclass Phenothiazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzothiazines
• Subclass: Phenothiazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenothiazines
• Alternative Parents: Diarylthioethers Indoles Alkylarylthioethers Benzenoids 1,4-thiazines 1,2,4-triazines Tertiary carboxylic acid amides Pyrroles Heteroaromatic compounds Sulfenyl compounds Azacyclic compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenothiazine - Diarylthioether - Indole - Indole or derivatives - Aryl thioether - Alkylarylthioether - Para-thiazine - Triazine - Benzenoid - 1,2,4-triazine - Heteroaromatic compound - Pyrrole - Tertiary carboxylic acid amide - Carboxamide group - Azacycle - Sulfenyl compound - Carboxylic acid derivative - Thioether - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organosulfur compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine 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

Associated Targets(Human)

SIRT1 Tchem NAD-dependent protein deacetylase sirtuin-1 (1 Activities)

Discover Target: SIRT1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 469.600 g/mol
• XLogP3: 5.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 469.103 Da
• Monoisotopic Mass: 469.103 Da
• Topological Polar Surface Area: 125.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 690.000
• 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