518303-20-3

Basic information

• Product Name: UMI-77
• Synonyms: 2-[[4-[[(4-bromophenyl)sulfonyl]amino]-1-hydroxy-2-naphthalenyl]thio]-acetic acid;2-[4-[(4-Bromophenyl)sulfonylamino]-1-hydroxynaphthalen-2-yl]sulfanylacetic acid UMI-77;2-((4-(4-Bromophenylsulfonamido)-1-hydroxynaphthalen-2-yl)thio)acetic acid;Acetic acid, 2-[[4-[[(4-bromophenyl)sulfonyl]amino]-1-hydroxy-2-naphthalenyl]thio]-
• CAS NO: 518303-20-3
• Molecular Formula: C₁₈H₁₄BrNO₅S₂
• Molecular Weight: 468.34146
• Product Categories: Inhibitors
• Mol File: 518303-20-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 661.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.79±0.1 g/cm3(Predicted)
• Solubility: ≥23.4 mg/mL in DMSO; insoluble in H2O; ≥7.2 mg/mL in EtOH
• PKA: 2.41±0.30(Predicted)
• CAS DataBase Reference: UMI-77(CAS DataBase Reference)
• NIST Chemistry Reference: UMI-77(518303-20-3)
• EPA Substance Registry System: UMI-77(518303-20-3)

Safety Data

• Hazardous Substances Data: 518303-20-3(Hazardous Substances Data)

Usage

Description

UMI-77 is a small molecule inhibitor that targets Mcl-1, a protein that plays a crucial role in pancreatic cancer cell growth. By inhibiting Mcl-1, UMI-77 effectively blocks and attenuates the growth of pancreatic cancer cells, making it a promising anticancer agent.

Uses

Used in Anticancer Applications:
UMI-77 is used as an anticancer agent for pancreatic cancer. It functions by inhibiting the Mcl-1 protein, which is essential for the growth and survival of pancreatic cancer cells. This inhibition leads to the attenuation of cancer cell growth and potentially contributes to the treatment of pancreatic cancer.
Used in Pharmaceutical Industry:
UMI-77 is used as a small molecule inhibitor for research and development in the pharmaceutical industry. Its ability to target Mcl-1 makes it a valuable tool for studying the underlying mechanisms of pancreatic cancer and for developing new therapeutic strategies against this disease.

Biological Activity

umi-77 is a novel small-molecule inhibitor of mcl-1 with ki and ic50 values of 0.49 μm and 0.31 μm [1].myeloid cell leukemia-1 (mcl-1) is a member of the prosurvival bcl-2 family and is a potent anti-apoptotic protein. mcl-1 acts as an important survival factor in a broad range of human cancers [1].umi-77 is a novel small-molecule mcl-1 inhibitor. in fp-based binding assays, umi-77 potently and selectively displaced fluorescent labeled bid-bh3 peptide from mcl-1 protein with ki value of 0.49μm and bound to the bh3 binding pocket of mcl-1 protein. umi-77 bound to a1/bfl-1, bcl-w, bcl-2 and bcl-xl with ki values of 5.33, 8.19, 23.83 and 32.99μm. in a pull-down assay, umi-77 at 10 μm effectively and dose-dependently inhibited the interactions between bl-noxa and cellular mcl-1. it was reported that mcl-1 regulates pro-apoptotic bax and bak proteins and preventing their pro-apoptotic activity. umi-77 dose-dependently inhibited the binding of mcl-1 to bax with ic50 value of 1.43μm. in pc cells, umi-77 inhibited cell growth and induced apoptosis in a time and dose-dependent way [1].in bxpc-3 xenografted scid mice model, umi-77 exhibited robust anti-tumor efficacy with no toxicity. also, umi-77 decreased the anti-apoptotic protein survivin, which potently inhibited apoptosis by antagonizing caspase activity [1].

references

[1]. abulwerdi f, liao c, liu m, azmi as, et al. a novel small-molecule inhibitor of mcl-1 blocks pancreatic cancer growth in vitro and in vivo. mol cancer ther, 2014, 13(3): 565-575.

Upstream product

• 1429764-30-6 methyl 2-((4-(4-bromophenylsulfonamido)-1-methoxynaphthalen-2-yl)thio)acetate? 
• 1429765-78-5 methyl 2-((4-amino-1-methoxynaphthalen-2-yl)thio)acetate 
• 1429765-71-8 methyl 2-((1-methoxy-4-nitronaphthalen-2-yl)thio)acetate 
• 4900-63-4 1-methoxy-4-nitronaphthalene 
• 1429765-70-7 2-iodo-1-methoxy-4-nitronaphthalene 

Downstream Products

• 1429764-29-3 2-((1-acetoxy-4-(4-bromophenylsulfonamido)naphthalen-2-yl)thio)acetic acid 

Relevant articles and documents

3-substituted-N-(4-hydroxynaphthalen-1-yl)arylsulfonamides as a novel class of selective Mcl-1 inhibitors: Structure-based design, synthesis, SAR, and biological evaluation

Mcl-1, an antiapoptotic member of the Bcl-2 family of proteins, is a validated and attractive target for cancer therapy. Overexpression of Mcl-1 in many cancers results in disease progression and resistance to current chemotherapeutics. Utilizing high-throughput screening, compound 1 was identified as a selective Mcl-1 inhibitor and its binding to the BH3 binding groove of Mcl-1 was confirmed by several different, but complementary, biochemical and biophysical assays. Guided by structure-based drug design and supported by NMR experiments, comprehensive SAR studies were undertaken and a potent and selective inhibitor, compound 21, was designed which binds to Mcl-1 with a Ki of 180 nM. Biological characterization of 21 showed that it disrupts the interaction of endogenous Mcl-1 and biotinylated Noxa-BH3 peptide, causes cell death through a Bak/Bax-dependent mechanism, and selectively sensitizes Eμ-myc lymphomas overexpressing Mcl-1, but not Eμ-myc lymphoma cells overexpressing Bcl-2. Treatment of human leukemic cell lines with compound 21 resulted in cell death through activation of caspase-3 and induction of apoptosis.