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SML1881

Sigma-Aldrich

PBOX-6

≥98% (HPLC)

Synonym(s):

6-(Naphthalen-1-yl)benzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-yl dimethylcarbamate, 7-[[Dimethylcarbamoyl]oxy]-6-(1-naphthyl)pyrrolo-[2,1-d](1,5)-benzoxazepine, Dimethyl-carbamic acid 5-naphthalen-1-yl-6-oxa-10b-aza-benzo[e]azulen-4-yl ester, PBOX6

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About This Item

Empirical Formula (Hill Notation):
C25H20N2O3
CAS Number:
290814-68-5
Molecular Weight:
396.44
UNSPSC Code:
12352202

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

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

InChI

1S/C25H20N2O3/c1-26(2)25(28)30-24-21-14-8-16-27(21)20-13-5-6-15-22(20)29-23(24)19-12-7-10-17-9-3-4-11-18(17)19/h3-16H,1-2H3

InChI key

SOIZAFVNIXAZFQ-UHFFFAOYSA-N

Biochem/physiol Actions

A tubulin-targeting, anti-microtubule agent that induces apoptosis in cancer cells and inhibits tumour growth in mice in vivo.
PBOX-6 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 = 2.28 μM/HL60-MDR1, 2.86 μM/HL60-ABCG2, 1.91 μM/HL60; IC50 = 4.71 μM/A2780-ADR, 4.10 μM/A2780). PBOX-6 inhibits the assembly of purified tubulin in cell-free assays and causes microtubule depolymerization in MCF-7 cells by binding a tubulin site distinct from those targeted by vinblastine and colchicine. When administered via intratumoral injection (7.5 mg/kg/day) in vivo, PBOX-6 is reported to significantly inhibit tumour growth in a murine model of neuroblastoma and a CML model of the imatinib-resistant T315I mutants.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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D M Zisterer et al.
The Journal of pharmacology and experimental therapeutics, 293(1), 48-59 (2000-03-29)
Some, but not all, of a series of novel pyrrolo-1,5-benzoxazepines (PBOXs) induce apoptosis as shown by cell shrinkage, chromatin condensation, and DNA fragmentation in three human cell lines, HL-60 promyelocytic, Jurkat T lymphoma, and Hut-78 s.c. lymphoma cells. This chemical
Jennifer C Lennon et al.
Investigational new drugs, 34(5), 663-676 (2016-06-24)
Neuroblastoma, a paediatric malignancy of the sympathetic nervous system, accounts for 15 % of childhood cancer deaths. Despite advances in understanding the biology, it remains one of the most difficult paediatric cancers to treat partly due to the development of multidrug
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

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