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Merck
CN

SML4032

Sigma-Aldrich

CPSF3-IN-1

≥98% (HPLC)

Synonym(s):

3-(1,3-Ddihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(40- acetyl-1,10-biphenyl-3-yl) propanamide, N-(4′-Acetyl[1,1′-biphenyl]-3-yl)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole-7-propanamide; benzoxaborole 1

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Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(NC1=CC(C2=CC=C(C=C2)C(C)=O)=CC=C1)CCC3=CC=CC4=C3B(OC4)O

InChI

1S/C24H22BNO4/c1-16(27)17-8-10-18(11-9-17)20-5-3-7-22(14-20)26-23(28)13-12-19-4-2-6-21-15-30-25(29)24(19)21/h2-11,14,29H,12-13,15H2,1H3,(H,26,28)

InChI key

KANKQAZGSKQFCK-UHFFFAOYSA-N

Biochem/physiol Actions

Cell penetrant, potent and selective inhibitor of endonuclease activity of CPSF3 in vitro that limits transcriptional termination in cells.
CPSF3-IN-1 (3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(40- acetyl-1,10-biphenyl-3-yl) propenamide) is a cell penetrant, potent and selective inhibitor of endonuclease activity of CPSF3 (cleavage and polyadenylation specific factor 3) in vitro that limits transcriptional termination in cells. CPSF3-IN-1 binds to CPSF3 active site and causes transcription readthrough. It potently inhibits growth of numerous cancer cell lines (IC50 = 0.28 µM HCT116 cells).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Ye Tao et al.
Cell chemical biology, 31(1), 139-149 (2023-11-16)
A novel class of benzoxaboroles was reported to induce cancer cell death but the mechanism was unknown. Using a forward genetics platform, we discovered mutations in cleavage and polyadenylation specific factor 3 (CPSF3) that reduce benzoxaborole binding and confer resistance.
Jiong Zhang et al.
Journal of medicinal chemistry, 62(14), 6765-6784 (2019-07-03)
Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has

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