≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
M3258 is an orally bioavailable, potent, reversible and highly selective immunoproteasome subunit LMP7 (β5i) inhibitor. M3258 exerts high biochemical ( IC 50 =3.6 nM) and cellular ( IC 50 =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
In Vitro
M3258 inhibits human LMP7 with a mean IC 50 of 4.1 nM. M3258 displays weak activity against the constitutive proteasome subunit β5 (mean IC 50 =2519 nM). M3258 potently inhibits LMP7 in the human multiple myeloma cell lines MM.1S and U266B1 and in human, rat, and dog PBMCs with IC 50 s between 2 and 37 nM. M3258 induces a >four fold accumulation of ubiquitinated proteins with an EC 50 of 1980 nM in MM.1S cells. M3258 interferes with immunoproteasome function. M3258 also induces apoptosis assessed by caspase 3/7 activity (EC 50 =420 nM;>3.5-fold induction) and reduces MM.1S cell viability (IC 50 =367 nM). MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: MM.1S cells Concentration: 0.01-100 nM Incubation Time: 2 hours Result: Potently inhibited LMP7 in the human multiple myeloma cell lines MM.1S (IC 50 =2.2 nM).
In Vivo
M3258 (1 mg/kg; 10 mg/kg) shows superior antitumor efficacy in selected multiple myeloma and mantle cell lymphoma xenograft models compared with the approved nonselective proteasome inhibitors bortezomib and ixazomib. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female H2d Rag2 mice or female CB-17 SCID mice (U266B1 subcutaneous xenograft model; MM.1S subcutaneous xenograft model)Dosage: 1 mg/kg in U266B1 subcutaneous xenograft model; 10 mg/kg in MM.1S subcutaneous xenograft model Administration: P.o.; either once daily, every 2 days or twice weekly (days 1 and 4) Result: Displayed significant and strong antitumor efficacy.
Form:Solid
IC50& Target:LMP7
| Canonical Smiles | B(C(CC1=COC2=CC=CC=C21)NC(=O)C3CC4CCC3O4)(O)O |
|---|---|
| IUPAC Name | [(1R)-2-(1-benzofuran-3-yl)-1-[[(1S,2R,4R)-7-oxabicyclo[2.2.1]heptane-2-carbonyl]amino]ethyl]boronic acid |
| InChIKey | RFQDLTYXNINJON-OYNZBZHQSA-N |
| 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 |
| Isomeric SMILES | B([C@H](CC1=COC2=CC=CC=C21)NC(=O)[C@@H]3C[C@H]4CC[C@@H]3O4)(O)O |
| PubChem CID | 138319683 |
| MeSH Entry Terms | ((1R)-2-(1-benzofuran-3-yl)-1-(((1S,2R,4R)-7-oxabicyclo(2.2.1)heptane-2-carbonyl)amino)ethyl)boronic acid;M3258 |
| Molecular Weight | 329.16 |
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Benzofurans |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzofurans |
| Alternative Parents | Benzenoids Tetrahydrofurans Heteroaromatic compounds Furans Secondary carboxylic acid amides Boronic acids Oxacyclic compounds Organic metalloid salts Dialkyl ethers Organopnictogen compounds Organonitrogen compounds Organic oxides Monoalkylboranes Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Benzofuran - Benzenoid - Heteroaromatic compound - Tetrahydrofuran - Furan - Secondary carboxylic acid amide - Carboxamide group - Boronic acid - Boronic acid derivative - Oxacycle - Organic metalloid salt - Ether - Dialkyl ether - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Monoalkylborane - Alkylborane - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organooxygen compound - Organonitrogen compound - Organoboron compound - Carbonyl group - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. |
| External Descriptors | Not available |
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| Solubility | DMSO : 250 mg/mL (759.51 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 329.200 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Exact Mass | 329.143 Da |
| Monoisotopic Mass | 329.143 Da |
| Topological Polar Surface Area | 91.900 Ų |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Complexity | 476.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| 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 |
