PBOX-15
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406743

CAS#: 354759-10-7

Description: PBOX-15 is a novel microtubule targeting agent, induces apoptosis, upregulates death receptors, and potentiates TRAIL-mediated apoptosis in multiple myeloma cells. PBOX-15 inhibits T-cell migration via post-translational modifications of tubulin. PBOX-15 induces apoptosis, upregulates death receptors, and potentiates TRAIL-mediated apoptosis in multiple myeloma cells. PBOX-15 induces apoptosis and improves the efficacy of oxaliplatin in human colorectal cancer cell lines.


Chemical Structure

img
PBOX-15
CAS# 354759-10-7

Theoretical Analysis

MedKoo Cat#: 406743
Name: PBOX-15
CAS#: 354759-10-7
Chemical Formula: C28H19NO3
Exact Mass: 417.14
Molecular Weight: 417.464
Elemental Analysis: C, 80.56; H, 4.59; N, 3.36; O, 11.50

Price and Availability

Size Price Availability Quantity
5mg USD 230
25mg USD 570
Bulk inquiry

Synonym: PBOX-15; PBOX15; PBOX 15.

IUPAC/Chemical Name: 5-(naphthalen-1-yl)naphtho[2,3-b]pyrrolo[1,2-d][1,4]oxazepin-4-yl acetate

InChi Key: STVDRIIZTGYIMM-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CC(OC1=C(C2=C3C=CC=CC3=CC=C2)OC4=CC5=CC=CC=C5C=C4N6C1=CC=C6)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: PBOX-15 is a novel microtubule targeting agent.
In vitro activity: PBOX-15 enhanced TRAIL-induced apoptosis by dual activation of extrinsic and intrinsic apoptotic pathways. The specific caspase-8 inhibitor, Z-IETD-FMK, identified the extrinsic pathway as the principal mode of apoptosis. This study demonstrates that PBOX-15 can enhance TRAIL-induced apoptosis by upregulation of DR5, reduction of cellular mitochondrial potential, activation of the caspase cascade and downregulation of PI3K/Akt, c-FLIP, Mcl-1 and IAP survival pathways. Reference: Int J Oncol. 2016 Jul;49(1):74-88. https://pubmed.ncbi.nlm.nih.gov/27176505/
In vivo activity: TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 417.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Nathwani SM, Greene LM, Butini S, Campiani G, Williams DC, Samali A, Szegezdi E, Zisterer DM. The pyrrolo-1,5-benzoxazepine, PBOX-15, enhances TRAIL‑induced apoptosis by upregulation of DR5 and downregulation of core cell survival proteins in acute lymphoblastic leukaemia cells. Int J Oncol. 2016 Jul;49(1):74-88. doi: 10.3892/ijo.2016.3518. Epub 2016 May 12. PMID: 27176505; PMCID: PMC4902072. 2. Kinsella P, Greene LM, Bright SA, Pollock JK, Butini S, Campiani G, Bauer S, Williams DC, Zisterer DM. The novel pyrrolo-1,5-benzoxazepine, PBOX-15, synergistically enhances the apoptotic efficacy of imatinib in gastrointestinal stromal tumours; suggested mechanism of action of PBOX-15. Invest New Drugs. 2016 Apr;34(2):159-67. doi: 10.1007/s10637-016-0331-1. Epub 2016 Feb 17. PMID: 26885657.
In vitro protocol: 1. Nathwani SM, Greene LM, Butini S, Campiani G, Williams DC, Samali A, Szegezdi E, Zisterer DM. The pyrrolo-1,5-benzoxazepine, PBOX-15, enhances TRAIL‑induced apoptosis by upregulation of DR5 and downregulation of core cell survival proteins in acute lymphoblastic leukaemia cells. Int J Oncol. 2016 Jul;49(1):74-88. doi: 10.3892/ijo.2016.3518. Epub 2016 May 12. PMID: 27176505; PMCID: PMC4902072. 2. Kinsella P, Greene LM, Bright SA, Pollock JK, Butini S, Campiani G, Bauer S, Williams DC, Zisterer DM. The novel pyrrolo-1,5-benzoxazepine, PBOX-15, synergistically enhances the apoptotic efficacy of imatinib in gastrointestinal stromal tumours; suggested mechanism of action of PBOX-15. Invest New Drugs. 2016 Apr;34(2):159-67. doi: 10.1007/s10637-016-0331-1. Epub 2016 Feb 17. PMID: 26885657.
In vivo protocol: TBD

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Nathwani SM, Greene LM, Butini S, Campiani G, Williams DC, Samali A, Szegezdi E, Zisterer DM. The pyrrolo-1,5-benzoxazepine, PBOX-15, enhances TRAIL induced apoptosis by upregulation of DR5 and downregulation of core cell survival proteins in acute lymphoblastic leukaemia cells. Int J Oncol. 2016 May 12. doi: 10.3892/ijo.2016.3518. [Epub ahead of print] PubMed PMID: 27176505.

2: Kinsella P, Greene LM, Bright SA, Pollock JK, Butini S, Campiani G, Bauer S, Williams DC, Zisterer DM. The novel pyrrolo-1,5-benzoxazepine, PBOX-15, synergistically enhances the apoptotic efficacy of imatinib in gastrointestinal stromal tumours; suggested mechanism of action of PBOX-15. Invest New Drugs. 2016 Apr;34(2):159-67. doi: 10.1007/s10637-016-0331-1. Epub 2016 Feb 17. PubMed PMID: 26885657.

3: Fiore D, Proto MC, Pisanti S, Picardi P, Pagano Zottola AC, Butini S, Gemma S, Casagni A, Laezza C, Vitale M, Ligresti A, Di Marzo V, Zisterer DM, Nathwani S, Williams DC, Campiani G, Gazzerro P, Bifulco M. Antitumor effect of pyrrolo-1,5-benzoxazepine-15 and its synergistic effect with Oxaliplatin and 5-FU in colorectal cancer cells. Cancer Biol Ther. 2015 Sep 21:0. [Epub ahead of print] PubMed PMID: 26392056.

4: O'Callaghan K, Palagano E, Butini S, Campiani G, Williams DC, Zisterer DM, O'Sullivan J. Induction of apoptosis in oral squamous carcinoma cells by pyrrolo-1,5-benzoxazepines. Mol Med Rep. 2015 Sep;12(3):3748-54. doi: 10.3892/mmr.2015.3832. Epub 2015 May 25. PubMed PMID: 26005189.

5: Retraction notice to “PBOX-15 induces apoptosis and improves the efficacy of oxaliplatin in human colorectal cancer cell lines” [Eur. J. Pharmacol. 714(1–3) (2013) 379–387]. Eur J Pharmacol. 2014 Apr 5;728:190. doi: 10.1016/j.ejphar.2014.01.024. PubMed PMID: 24795989.

6: Gangemi G, Gazzerro P, Fiore D, Proto MC, Butini S, Gemma S, Casagni A, Laezza C, Vitale M, Ligresti A, Di Marzo V, Zisterer DM, Nathwani S, Clive Williams D, Campiani G, Bifulco M. PBOX-15 induces apoptosis and improves the efficacy of oxaliplatin in human colorectal cancer cell lines. Eur J Pharmacol. 2013 Aug 15;714(1-3):379-87. doi: 10.1016/j.ejphar.2013.07.011. Epub 2013 Jul 16. Retraction in: Eur J Pharmacol. 2014 Apr 5;728:190. PubMed PMID: 23872382.

7: Lysaght J, Verma NK, Maginn EN, Ryan JM, Campiani G, Zisterer DM, Williams DC, Browne PV, Lawler MP, McElligott AM. The microtubule targeting agent PBOX-15 inhibits integrin-mediated cell adhesion and induces apoptosis in acute lymphoblastic leukaemia cells. Int J Oncol. 2013 Jan;42(1):239-46. doi: 10.3892/ijo.2012.1688. Epub 2012 Nov 6. PubMed PMID: 23135704.

8: Maginn EN, Browne PV, Hayden P, Vandenberghe E, MacDonagh B, Evans P, Goodyer M, Tewari P, Campiani G, Butini S, Williams DC, Zisterer DM, Lawler MP, McElligott AM. PBOX-15, a novel microtubule targeting agent, induces apoptosis, upregulates death receptors, and potentiates TRAIL-mediated apoptosis in multiple myeloma cells. Br J Cancer. 2011 Jan 18;104(2):281-9. doi: 10.1038/sj.bjc.6606035. Epub 2010 Dec 21. PubMed PMID: 21179037; PubMed Central PMCID: PMC3031893.

9: Forde JC, Maginn EN, McNamara G, Martin LM, Campiani G, Williams DC, Zisterer D, McElligott AM, Lawler M, Lynch TH, Hollywood D, Marignol L. Microtubule-targeting-compound PBOX-15 radiosensitizes cancer cells in vitro. Cancer Biol Ther. 2011 Feb 15;11(4):421-8. Epub 2011 Feb 15. PubMed PMID: 21131779.

10: Nathwani SM, Cloonan SM, Stronach M, Campiani G, Lawler M, Williams DC, Zisterer DM. Novel microtubule-targeting agents, pyrrolo-1,5-benzoxazepines, induce cell cycle arrest and apoptosis in prostate cancer cells. Oncol Rep. 2010 Dec;24(6):1499-507. PubMed PMID: 21042745.

11: Nathwani SM, Butler S, Fayne D, McGovern NN, Sarkadi B, Meegan MJ, Lloyd DG, Campiani G, Lawler M, Williams DC, Zisterer DM. Novel microtubule-targeting agents, pyrrolo-1,5-benzoxazepines, induce apoptosis in multi-drug-resistant cancer cells. Cancer Chemother Pharmacol. 2010 Aug;66(3):585-96. doi: 10.1007/s00280-009-1200-9. Epub 2009 Dec 18. PubMed PMID: 20020128.

12: McElligott AM, Maginn EN, Greene LM, McGuckin S, Hayat A, Browne PV, Butini S, Campiani G, Catherwood MA, Vandenberghe E, Williams DC, Zisterer DM, Lawler M. The novel tubulin-targeting agent pyrrolo-1,5-benzoxazepine-15 induces apoptosis in poor prognostic subgroups of chronic lymphocytic leukemia. Cancer Res. 2009 Nov 1;69(21):8366-75. doi: 10.1158/0008-5472.CAN-09-0131. Epub 2009 Oct 13. PubMed PMID: 19826055.

13: Verma NK, Dempsey E, Conroy J, Olwell P, Mcelligott AM, Davies AM, Kelleher D, Butini S, Campiani G, Williams DC, Zisterer DM, Lawler M, Volkov Y. A new microtubule-targeting compound PBOX-15 inhibits T-cell migration via post-translational modifications of tubulin. J Mol Med (Berl). 2008 Apr;86(4):457-69. doi: 10.1007/s00109-008-0312-8. Epub 2008 Feb 13. PubMed PMID: 18270678.

14: Greene LM, Campiani G, Lawler M, Williams DC, Zisterer DM. BubR1 is required for a sustained mitotic spindle checkpoint arrest in human cancer cells treated with tubulin-targeting pyrrolo-1,5-benzoxazepines. Mol Pharmacol. 2008 Feb;73(2):419-30. Epub 2007 Nov 8. PubMed PMID: 17991869.

15: Mulligan JM, Greene LM, Cloonan S, Mc Gee MM, Onnis V, Campiani G, Fattorusso C, Lawler M, Williams DC, Zisterer DM. Identification of tubulin as the molecular target of proapoptotic pyrrolo-1,5-benzoxazepines. Mol Pharmacol. 2006 Jul;70(1):60-70. Epub 2006 Mar 29. PubMed PMID: 16571652.