YM155 (Sepantronium Bromide) - ≥98% , CAS No.781661-94-7

CAS: 781661-94-7 Cat. No.: Y126171 Molecular Weight: 443.29 PubChem CID: 11178236

GRADE & PURITY ≥98%

Synonyms

3-(2-METHOXYETHYL)-2-METHYL-4,9-DIOXO-1-(PYRAZIN-2-YLMETHYL)NAPHTHO[2,3-D]IMIDAZOL-1-IUM BROMIDE | bromuro de sepantronio | 3-(2-Methoxyethyl)-2-methyl-4,9-dioxo-1-pyrazin-2-ylmethyl-4,9-dihydro-3H-naphtho[2,3-d]imidazol-1-ium bromide | SEPANTRONIUM BROMI

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

YM155 (Sepantronium Bromide) is a potent survivin suppressant by inhibiting Survivin promoter activity with IC50 of 0.54 nM in HeLa-SURP-luc and CHO-SV40-luc cells; does not significantly inhibit SV40 promoter activity, but is observed to slightly inhibited Survivin and XIAP interact.
An inhibitor of survivin expression and apoptosis inducer.

Specifications

Synonyms

3-(2-METHOXYETHYL)-2-METHYL-4, 9-DIOXO-1-(PYRAZIN-2-YLMETHYL)NAPHTHO[2, 3-D]IMIDAZOL-1-IUM BROMIDE | bromuro de sepantronio | 3-(2-Methoxyethyl)-2-methyl-4, 9-dioxo-1-pyrazin-2-ylmethyl-4, 9-dihydro-3H-naphtho[2, 3-d]imidazol-1-ium bromide | SEPANTRONIUM BROMI

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

YM155 is a small molecule inhibitor of survivin expression that acts by inhibiting the survivin gene promoter transcription. Shown to induce apoptosis and inhibit tumor growth.

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.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=[N+](C2=C(N1CCOC)C(=O)C3=CC=CC=C3C2=O)CC4=NC=CN=C4.[Br-]
• IUPAC Name: 1-(2-methoxyethyl)-2-methyl-3-(pyrazin-2-ylmethyl)benzo[f]benzimidazol-3-ium-4,9-dione;bromide
• InChIKey: QBIYUDDJPRGKNJ-UHFFFAOYSA-M
• INCHI: 1S/C20H19N4O3.BrH/c1-13-23(9-10-27-2)17-18(24(13)12-14-11-21-7-8-22-14)20(26)16-6-4-3-5-15(16)19(17)25;/h3-8,11H,9-10,12H2,1-2H3;1H/q+1;/p-1
• Isomeric SMILES: CC1=[N+](C2=C(N1CCOC)C(=O)C3=CC=CC=C3C2=O)CC4=NC=CN=C4.[Br-]
• PubChem CID: 11178236
• Molecular Weight: 443.29

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthalenes
• Alternative Parents: Aryl ketones Pyrazines N-substituted imidazoles Vinylogous amides Heteroaromatic compounds Dialkyl ethers Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Organic bromide salts Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Naphthalene - Aryl ketone - N-substituted imidazole - Pyrazine - Azole - Imidazole - Heteroaromatic compound - Vinylogous amide - Ketone - Azacycle - Ether - Dialkyl ether - Organoheterocyclic compound - Organic bromide salt - Organic salt - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
• 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)

PAK1 Tchem Serine/threonine-protein kinase PAK 1 (2601 Activities)

Discover Target: PAK1

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DU-145 (51482 Activities)

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PC-3 (62116 Activities)

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A549 (127892 Activities)

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HUVEC (11049 Activities)

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MDA-MB-435 (38290 Activities)

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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CHO-K1 (1115 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Chorioallantoic membrane (375 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (>89 mg/ml), DMSO (>89 mg/ml), ethanol (>24 mg/ml), DMF (~3 mg/ml), and PBS (pH 7.2) (~10 mg/ml).
• Molecular Weight: 443.300 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 442.064 Da
• Monoisotopic Mass: 442.064 Da
• Topological Polar Surface Area: 78.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 571.000
• 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: 2

XLogP3

References

1. Fabiao Hu, Changping Deng, Yiwen Zhou, Yuping Liu, Tong Zhang, Peiwen Zhang, Zhangting Zhao, Hui Miao, Wenyun Zheng, Wenliang Zhang, Meiyan Wang, Xingyuan Ma.  (2021)  Multistage targeting and dual inhibiting strategies based on bioengineered tumor matrix microenvironment-mediated protein nanocages for enhancing cancer biotherapy.  Bioengineering & Translational Medicine,  7  (2): (e10290).  [PMID:35600646] [10.1002/btm2.10290]

2. Jang Hye-Jeong, Chung In-Young, Lim Changjin, Chung Sungkyun, Kim Bi-o, Kim Eun Sook, Kim Seok-Ho, Cho You-Hee.  (2019)  Redirecting an Anticancer to an Antibacterial Hit Against Methicillin-Resistant Staphylococcus aureus.  Frontiers in Microbiology,      [PMID:30858845] [10.3389/fmicb.2019.00350]