Diazepinomicin

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

MedKoo CAT#: 206008

CAS#: 733035-26-2

Description: Diazepinomicin, also known as TLN-4601 and BU 4664L, is a small-molecule inhibitor of the RAS/RAF/MAPK signaling pathway with potential antineoplastic activity. Diazepinomicin binds to and inhibits Ras kinase, thereby preventing the phosphorylation and activation of proteins downstream of the Ras signal transduction pathway, including serine/threonine kinase RAF (BRAF) and extracellular signal-regulated kinases 1 and 2 (ERK1 and ERK-2). This agent also selectively binds to the peripheral benzodiazepine receptor (PBR), a receptor highly expressed in certain tumor cell types cells, inducing cell cycle arrest and apoptosis in PBR-expressing cells. Diazepinomicin can cross the blood-brain barrier (BBB).

Chemical Structure

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Diazepinomicin
CAS# 733035-26-2
Instruction

Theoretical Analysis

MedKoo Cat#: 206008
Name: Diazepinomicin
CAS#: 733035-26-2
Chemical Formula: C28H34N2O4
Exact Mass: 462.25
Molecular Weight: 462.580
Elemental Analysis: C, 72.70; H, 7.41; N, 6.06; O, 13.83

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: ECO 4601; ECO-4601; ECO4601; TLN4601; TLN 4601; TLN-4601; BU 4664L; BU-4664L; BU4664L; Diazepinomicin.

IUPAC/Chemical Name: 4,6,8-trihydroxy-10-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)-5H-dibenzo[b,e][1,4]diazepin-11(10H)-one

InChi Key: SALVHVNECODMJP-GNUCVDFRSA-N

InChi Code: InChI=1S/C28H34N2O4/c1-18(2)8-5-9-19(3)10-6-11-20(4)14-15-30-23-16-21(31)17-25(33)27(23)29-26-22(28(30)34)12-7-13-24(26)32/h7-8,10,12-14,16-17,29,31-33H,5-6,9,11,15H2,1-4H3/b19-10+,20-14+

SMILES Code: O=C1C2=CC=CC(O)=C2NC3=C(O)C=C(O)C=C3N1C/C=C(C)/CC/C=C(C)/CC/C=C(C)\C

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: >5 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:         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 462.58 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:
In vitro protocol:
In vivo protocol:

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1: Abdelmohsen UR, Szesny M, Othman EM, Schirmeister T, Grond S, Stopper H, Hentschel U. Antioxidant and anti-protease activities of diazepinomicin from the sponge-associated Micromonospora strain RV115. Mar Drugs. 2012 Oct;10(10):2208-21. doi: 10.3390/md10102208. Epub 2012 Oct 8. PubMed PMID: 23170078; PubMed Central PMCID: PMC3497017.

2: Mason WP, Belanger K, Nicholas G, Vallières I, Mathieu D, Kavan P, Desjardins A, Omuro A, Reymond D. A phase II study of the Ras-MAPK signaling pathway inhibitor TLN-4601 in patients with glioblastoma at first progression. J Neurooncol. 2012 Apr;107(2):343-9. doi: 10.1007/s11060-011-0747-6. Epub 2011 Nov 3. PubMed PMID: 22048878.

3: Campbell PM, Boufaied N, Fiordalisi JJ, Cox AD, Falardeau P, Der CJ, Gourdeau H. TLN-4601 suppresses growth and induces apoptosis of pancreatic carcinoma cells through inhibition of Ras-ERK MAPK signaling. J Mol Signal. 2010 Nov 2;5:18. doi: 10.1186/1750-2187-5-18. PubMed PMID: 21044336; PubMed Central PMCID: PMC2990749.

4: Bertomeu T, Zvereff V, Ibrahim A, Zehntner SP, Aliaga A, Rosa-Neto P, Bedell BJ, Falardeau P, Gourdeau H. TLN-4601 peripheral benzodiazepine receptor (PBR/TSPO) binding properties do not mediate apoptosis but confer tumor-specific accumulation. Biochem Pharmacol. 2010 Nov 15;80(10):1572-9. doi: 10.1016/j.bcp.2010.07.018. Epub 2010 Jul 22. PubMed PMID: 20655882.

5: Boufaied N, Wioland MA, Falardeau P, Gourdeau H. TLN-4601, a novel anticancer agent, inhibits Ras signaling post Ras prenylation and before MEK activation. Anticancer Drugs. 2010 Jun;21(5):543-52. doi: 10.1097/CAD.0b013e328337f373. PubMed PMID: 20220516.

6: Ratnayake AS, Janso JE, Feng X, Schlingmann G, Goljer I, Carter GT. Evaluating indole-related derivatives as precursors in the directed biosynthesis of diazepinomicin analogues. J Nat Prod. 2009 Mar 27;72(3):496-9. doi: 10.1021/np800664u. PubMed PMID: 19199816.

7: Feng X, Ratnayake AS, Charan RD, Janso JE, Bernan VS, Schlingmann G, He H, Tischler M, Koehn FE, Carter GT. Probing natural product biosynthetic pathways using Fourier transform ion cyclotron resonance mass spectrometry. Bioorg Med Chem. 2009 Mar 15;17(6):2154-61. doi: 10.1016/j.bmc.2008.10.073. Epub 2008 Nov 5. PubMed PMID: 19028101.

8: McAlpine JB, Banskota AH, Charan RD, Schlingmann G, Zazopoulos E, Piraee M, Janso J, Bernan VS, Aouidate M, Farnet CM, Feng X, Zhao Z, Carter GT. Biosynthesis of diazepinomicin/ECO-4601, a Micromonospora secondary metabolite with a novel ring system. J Nat Prod. 2008 Sep;71(9):1585-90. doi: 10.1021/np800376n. Epub 2008 Aug 23. PubMed PMID: 18722414.

9: Gourdeau H, McAlpine JB, Ranger M, Simard B, Berger F, Beaudry F, Farnet CM, Falardeau P. Identification, characterization and potent antitumor activity of ECO-4601, a novel peripheral benzodiazepine receptor ligand. Cancer Chemother Pharmacol. 2008 May;61(6):911-21. Epub 2007 Jul 11. Erratum in: Cancer Chemother Pharmacol. 2009 Feb;63(3):569. Cancer Chemother Pharmacol. 2008 Oct 22. doi: 10.1007/s00280-008-0848-x. Farnet, Chris M [added]. PubMed PMID: 17622531.

10: Charan RD, Schlingmann G, Janso J, Bernan V, Feng X, Carter GT. Diazepinomicin, a new antimicrobial alkaloid from a marine Micromonospora sp. J Nat Prod. 2004 Aug;67(8):1431-3. PubMed PMID: 15332871.