MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 529709 | Name: F-14512 (free base)

Description:

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

F-14512 is a DNA topoisomerase II inhibitor potentially for the treatment of acute myeloid leukemia.

Chemical Structure

F-14512 (free base)
F-14512 (free base)
CAS#866874-63-7 (free base)

Theoretical Analysis

MedKoo Cat#: 529709

Name: F-14512 (free base)

CAS#: 866874-63-7 (free base)

Chemical Formula: C33H47N5O8

Exact Mass: 641.3425

Molecular Weight: 641.76

Elemental Analysis: C, 61.76; H, 7.38; N, 10.91; O, 19.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
866874-39-7 (HCl) 866874-63-7 (free base)
Synonym
F-14512; F14512; F14512
IUPAC/Chemical Name
2-((3-((4-((3-aminopropyl)amino)butyl)amino)propyl)amino)-N-((5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)acetamide
InChi Key
NUZMJDHDPVKFJN-TYDXHICZSA-N
InChi Code
InChI=1S/C33H47N5O8/c1-42-26-13-20(14-27(43-2)32(26)40)29-21-15-24-25(46-19-45-24)16-22(21)31(23-18-44-33(41)30(23)29)38-28(39)17-37-12-6-11-36-9-4-3-8-35-10-5-7-34/h13-16,23,29-31,35-37,40H,3-12,17-19,34H2,1-2H3,(H,38,39)/t23-,29+,30-,31+/m0/s1
SMILES Code
O=C(N[C@H]1[C@]2([H])[C@@](C(OC2)=O)([H])[C@H](C3=CC(OC)=C(O)C(OC)=C3)C4=C1C=C5OCOC5=C4)CNCCCNCCCCNCCCN
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 641.76 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
1: Tierny D, Serres F, Segaoula Z, Bemelmans I, Bouchaert E, Pétain A, Brel V, Couffin S, Marchal T, Nguyen L, Thuru X, Ferré P, Guilbaud N, Gomes B. Phase I Clinical Pharmacology Study of F14512, a New Polyamine-Vectorized Anticancer Drug, in Naturally Occurring Canine Lymphoma. Clin Cancer Res. 2015 Dec 1;21(23):5314-23. doi: 10.1158/1078-0432.CCR-14-3174. PubMed PMID: 26169968. 2: Mouawad F, Gros A, Rysman B, Bal-Mahieu C, Bertheau C, Horn S, Sarrazin T, Lartigau E, Chevalier D, Bailly C, Lansiaux A, Meignan S. The antitumor drug F14512 enhances cisplatin and ionizing radiation effects in head and neck squamous carcinoma cell lines. Oral Oncol. 2014 Feb;50(2):113-9. doi: 10.1016/j.oraloncology.2013.11.003. PubMed PMID: 24290982. 3: Leblond P, Boulet E, Bal-Mahieu C, Pillon A, Kruczynski A, Guilbaud N, Bailly C, Sarrazin T, Lartigau E, Lansiaux A, Meignan S. Activity of the polyamine-vectorized anti-cancer drug F14512 against pediatric glioma and neuroblastoma cell lines. Invest New Drugs. 2014 Oct;32(5):883-92. doi: 10.1007/s10637-014-0132-3. PubMed PMID: 25008900. 4: Thibault B, Clement E, Zorza G, Meignan S, Delord JP, Couderc B, Bailly C, Narducci F, Vandenberghe I, Kruczynski A, Guilbaud N, Ferré P, Annereau JP. F14512, a polyamine-vectorized inhibitor of topoisomerase II, exhibits a marked anti-tumor activity in ovarian cancer. Cancer Lett. 2016 Jan 1;370(1):10-8. doi: 10.1016/j.canlet.2015.09.006. PubMed PMID: 26404751. 5: Kruczynski A, Pillon A, Créancier L, Vandenberghe I, Gomes B, Brel V, Fournier E, Annereau JP, Currie E, Guminski Y, Bonnet D, Bailly C, Guilbaud N. F14512, a polyamine-vectorized anti-cancer drug, currently in clinical trials exhibits a marked preclinical anti-leukemic activity. Leukemia. 2013 Nov;27(11):2139-48. doi: 10.1038/leu.2013.108. PubMed PMID: 23568148. 6: Ballot C, Jendoubi M, Kluza J, Jonneaux A, Laine W, Formstecher P, Bailly C, Marchetti P. Regulation by survivin of cancer cell death induced by F14512, a polyamine-containing inhibitor of DNA topoisomerase II. Apoptosis. 2012 Apr;17(4):364-76. doi: 10.1007/s10495-011-0681-2. PubMed PMID: 22127645. 7: Brel V, Annereau JP, Vispé S, Kruczynski A, Bailly C, Guilbaud N. Cytotoxicity and cell death mechanisms induced by the polyamine-vectorized anti-cancer drug F14512 targeting topoisomerase II. Biochem Pharmacol. 2011 Dec 15;82(12):1843-52. doi: 10.1016/j.bcp.2011.08.028. PubMed PMID: 21924246. 8: Gentry AC, Pitts SL, Jablonsky MJ, Bailly C, Graves DE, Osheroff N. Interactions between the etoposide derivative F14512 and human type II topoisomerases: implications for the C4 spermine moiety in promoting enzyme-mediated DNA cleavage. Biochemistry. 2011 Apr 19;50(15):3240-9. doi: 10.1021/bi200094z. PubMed PMID: 21413765; PubMed Central PMCID: PMC3086367. 9: Kruczynski A, Vandenberghe I, Pillon A, Pesnel S, Goetsch L, Barret JM, Guminski Y, Le Pape A, Imbert T, Bailly C, Guilbaud N. Preclinical activity of F14512, designed to target tumors expressing an active polyamine transport system. Invest New Drugs. 2011 Feb;29(1):9-21. doi: 10.1007/s10637-009-9328-3. PubMed PMID: 19777159. 10: Chelouah S, Monod-Wissler C, Bailly C, Barret JM, Guilbaud N, Vispé S, Käs E. An integrated Drosophila model system reveals unique properties for F14512, a novel polyamine-containing anticancer drug that targets topoisomerase II. PLoS One. 2011;6(8):e23597. doi: 10.1371/journal.pone.0023597. PubMed PMID: 21853156; PubMed Central PMCID: PMC3154508. 11: Barret JM, Kruczynski A, Vispé S, Annereau JP, Brel V, Guminski Y, Delcros JG, Lansiaux A, Guilbaud N, Imbert T, Bailly C. F14512, a potent antitumor agent targeting topoisomerase II vectored into cancer cells via the polyamine transport system. Cancer Res. 2008 Dec 1;68(23):9845-53. doi: 10.1158/0008-5472.CAN-08-2748. PubMed PMID: 19047165. 12: Annereau JP, Brel V, Dumontet C, Guminski Y, Imbert T, Broussas M, Vispé S, Bréand S, Guilbaud N, Barret JM, Bailly C. A fluorescent biomarker of the polyamine transport system to select patients with AML for F14512 treatment. Leuk Res. 2010 Oct;34(10):1383-9. doi: 10.1016/j.leukres.2009.12.021. PubMed PMID: 20096930. 13: Palermo G, Minniti E, Greco ML, Riccardi L, Simoni E, Convertino M, Marchetti C, Rosini M, Sissi C, Minarini A, De Vivo M. An optimized polyamine moiety boosts the potency of human type II topoisomerase poisons as quantified by comparative analysis centered on the clinical candidate F14512. Chem Commun (Camb). 2015 Oct 1;51(76):14310-3. doi: 10.1039/c5cc05065k. PubMed PMID: 26234198. 14: Pesnel S, Guminski Y, Pillon A, Lerondel S, Imbert T, Guilbaud N, Kruczynski A, Bailly C, Le Pape A. 99mTc-HYNIC-spermine for imaging polyamine transport system-positive tumours: preclinical evaluation. Eur J Nucl Med Mol Imaging. 2011 Oct;38(10):1832-41. doi: 10.1007/s00259-011-1857-2. PubMed PMID: 21660624.

View History

CCT-137690

CCT-137690

Featured