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Merck
CN

SML1895

Sigma-Aldrich

PBOX-15

≥98% (HPLC)

Synonym(s):

4-Acetoxy-5-(1-naphthyl) naphtho[2,3-b]pyrrolo[2,1-d][1,4]oxazepine, PBOX15, Pyrrolo-1,5-benzoxazepine-15

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About This Item

Empirical Formula (Hill Notation):
C28H19NO3
CAS Number:
354759-10-7
Molecular Weight:
417.46
UNSPSC Code:
12352202
NACRES:
NA.77

Key Documents

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Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC(OC1=C(C2=CC=CC3=C2C=CC=C3)OC4=C(N5C1=CC=C5)C=C6C=CC=CC6=C4)=O

InChI

1S/C28H19NO3/c1-18(30)31-28-24-14-7-15-29(24)25-16-20-9-2-3-10-21(20)17-26(25)32-27(28)23-13-6-11-19-8-4-5-12-22(19)23/h2-17H,1H3

InChI key

STVDRIIZTGYIMM-UHFFFAOYSA-N

Biochem/physiol Actions

A tubulin-targeting, anti-microtubule agent that induces apoptosis in cancer cells, including those exhibiting multi-drug resistance.
PBOX-15 belongs to a group of tubulin-targeting pyrrolo-1,5-benzoxazepine (PBOX) compounds that potently induce apoptosis in a wide spectrum of cancer cells, including those originating from the four main types of leukemia and those exhibiting multi-drug resistance (IC50 = 155 nM/HL60-MDR1, 252 nM/HL60-ABCG2, 210 nM/HL60). PBOX-15 inhibits the assembly of purified tubulin in cell-free assays and causes microtubule depolymerization in MCF-7 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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Certificates of Analysis (COA)

Lot/Batch Number
0000017496
0000017499
047M4734V

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Seema-Maria Nathwani et al.
International journal of oncology, 49(1), 74-88 (2016-05-14)
Apoptotic defects are frequently associated with poor outcome in pediatric acute lymphoblastic leukaemia (ALL) hence there is an ongoing demand for novel strategies that counteract apoptotic resistance. The death ligand TRAIL (tumour necrosis factor-related apoptosis-inducing ligand) and its selective tumour
Jude M Mulligan et al.
Molecular pharmacology, 70(1), 60-70 (2006-03-31)
We have demonstrated previously that certain members of a series of novel pyrrolo-1,5-benzoxazepine (PBOX) compounds potently induce apoptosis in a variety of human chemotherapy-resistant cancer cell lines and in primary ex vivo material derived from cancer patients. A better understanding
Paula Kinsella et al.
Investigational new drugs, 34(2), 159-167 (2016-02-18)
The C-KIT receptor tyrosine kinase is constitutively activated in the majority of gastrointestinal stromal tumours (GIST). Imatinib (IM) a selective inhibitor of C-KIT, is indicated for the treatment of KIT-positive unresectable and/or metastatic GIST, and has tripled the survival time

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