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M3258

CAT: 0804-HY-111790-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-111790-02Size:5 mg
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Description
M3258 is an orally bioavailable, potent, reversible and highly selective immunoproteasome subunit LMP7 (β5i) inhibitor. M3258 exerts high biochemical (IC50=3.6 nM) and cellular (IC50=3.4 nM) potency against the LMP7 subunit. M3258 shows strong antitumor efficacy in multiple myeloma xenograft models. M3258 leads to a significant and prolonged suppression of tumor LMP7 activity and ubiquitinated protein turnover and the induction of apoptosis in multiple myeloma cells[1][2].
CAS Number
2285330-15-4
UNSPSC
12352005
Target
Apoptosis; Proteasome
Type
Reference compound
Related Pathways
Apoptosis; Metabolic Enzyme/Protease
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/M-3258.html
Purity
98.0
Solubility
DMSO : 250 mg/mL (ultrasonic)
Smiles
O=C(N[C@@H](CC1=COC2=C1C=CC=C2)B(O)O)[C@H]3[C@@H]4CC[C@@H](O4)C3
Molecular Formula
C17H20BNO5
Molecular Weight
329.16
References & Citations
[1]Klein M, et al. Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i) [published online ahead of print, 2021 Jul 6]. J Med Chem. 2021;10.1021/acs.jmedchem.1c00604.|[2]Sanderson MP, et al. M3258 Is a Selective Inhibitor of the Immunoproteasome Subunit LMP7 (β5i) Delivering Efficacy in Multiple Myeloma Models [published online ahead of print, 2021 May 27]. Mol Cancer Ther. 2021;10.1158/1535-7163.MCT-21-0005.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 1

Chemical Information

M-3258

LMP7 Inhibitor M3258 is an orally bioavailable, potent, selective, reversible inhibitor of the large multifunctional peptidase 7 (LMP7, Beta5i, PSMB8), a chymotrypsin-like, proteolytic subunit of the immunoproteasome, with potential antineoplastic activity. Upon oral administration, LMP7 inhibitor M3258 targets and inhibits the proteolytic activity of the LMP7 subunit of immunoproteasome, thereby blocking its deubiquitylating activity. This blocks the ubiquitin proteasome degradation pathway, prevents the degradation of defective proteins, and leads to an accumulation of poly-ubiquitylated proteins. This induces the unfolded protein response (UPR) and results in both the induction of tumor cell apoptosis and the inhibition of tumor cell growth. Proteasomes are large multi-subunit protease complexes that degrade unneeded or damaged proteins that have been ubiquitinated, thereby restoring protein homeostasis. Unlike the constitutive proteasome, which is expressed in most tissues, immunoproteasome is specifically present in normal and malignant hematopoietic cells, including multiple myeloma. Immunoproteasome degrades ubiquitinated proteins, generates peptides for presentation on MHC class I, and plays a key role in the adaptive immune response and inflammatory diseases.

CAS Number2285330-15-4
PubChem CID138319683
IUPAC Name[(1R)-2-(1-benzofuran-3-yl)-1-[[(1S,2R,4R)-7-oxabicyclo[2.2.1]heptane-2-carbonyl]amino]ethyl]boronic acid
Molecular FormulaC17H20BNO5
Molecular Weight329.2
Topological Polar Surface Area91.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Heavy Atom Count24
Formal Charge0
Complexity476
SMILES
B([C@H](CC1=COC2=CC=CC=C21)NC(=O)[C@@H]3C[C@H]4CC[C@@H]3O4)(O)O
InChI
InChI=1S/C17H20BNO5/c20-17(13-8-11-5-6-15(13)24-11)19-16(18(21)22)7-10-9-23-14-4-2-1-3-12(10)14/h1-4,9,11,13,15-16,21-22H,5-8H2,(H,19,20)/t11-,13-,15+,16+/m1/s1
InChIKey
RFQDLTYXNINJON-OYNZBZHQSA-N
Chemical Structure
2D Structure
2D structure of M-3258
CAS: 2285330-15-4
CID: 138319683
Formula: C17H20BNO5
MW: 329.2
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight329.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass329.1434529
Monoisotopic Mass329.1434529
Topological Polar Surface Area91.9 Ų
Heavy Atom Count24
Formal Charge0
Complexity476
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
465513M3258