Tafluposide | F-11782 | CAS#179067-42-6 | DNA Topoisomerase Inhibitor

MedKoo Cat#: 528413 | Name: Tafluposide

Description:

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

Tafluposide, also known as F-11782, is a DNA topoisomerase inhibitor potentially for the treatment of solid tumors. Tafluposide induces delayed, but extensive, DNA strand breaks. Tafluposide showed significant cytotoxicity against cells derived from either hematological or solid tumors, with a marked inter-patient variation. There was no significant difference between the effect of tafluposide in samples from untreated or previously treated patients. Whilst tafluposide appeared to show weak cross-resistance with the topoisomerase II inhibitor etoposide in acute myeloid leukemia, there did not appear to be any correlation with the effect of the topoisomerase I inhibitor topotecan in either hematological or solid malignancies.

Chemical Structure

Tafluposide

CAS#179067-42-6

Theoretical Analysis

MedKoo Cat#: 528413

Name: Tafluposide

CAS#: 179067-42-6

Chemical Formula: C45H35F10O20P

Exact Mass: 1116.1300

Molecular Weight: 1116.71

Elemental Analysis: C, 48.40; H, 3.16; F, 17.01; O, 28.65; P, 2.77

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.

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Related CAS #

No Data

Synonym

Tafluposide, F-11782, F 11782, F11782

IUPAC/Chemical Name

(4aR,6R,7R,8S,8aR)-6-(((5S,5aR,8aR,9R)-9-(3,5-dimethoxy-4-(phosphonooxy)phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)oxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl bis(2-(perfluorophenoxy)acetate)

InChi Key

RTJVUHUGTUDWRK-WRGUAVMLSA-N

InChi Code

InChI=1S/C45H35F10O20P/c1-13-64-9-22-39(70-13)42(72-23(56)10-65-40-33(52)29(48)27(46)30(49)34(40)53)43(73-24(57)11-66-41-35(54)31(50)28(47)32(51)36(41)55)45(71-22)74-37-16-7-19-18(68-12-69-19)6-15(16)25(26-17(37)8-67-44(26)58)14-4-20(62-2)38(21(5-14)63-3)75-76(59,60)61/h4-7,13,17,22,25-26,37,39,42-43,45H,8-12H2,1-3H3,(H2,59,60,61)/t13?,17-,22+,25+,26-,37+,39+,42-,43+,45-/m0/s1

SMILES Code

O=C1OC[C@]2([H])[C@H](O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO4)O3)OC4C)OC(COC5=C(F)C(F)=C(F)C(F)=C5F)=O)OC(COC6=C(F)C(F)=C(F)C(F)=C6F)=O)C7=C(C=C8OCOC8=C7)[C@@H](C9=CC(OC)=C(OP(O)(O)=O)C(OC)=C9)[C@]21[H]

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,116.71 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.

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: Kluza J, Mazinghien R, Irwin H, Hartley JA, Bailly C. Relationships between DNA strand breakage and apoptotic progression upon treatment of HL-60 leukemia cells with tafluposide or etoposide. Anticancer Drugs. 2006 Feb;17(2):155-64. PubMed PMID: 16428933. 2: Pujol MD, Romero M, Sánchez I. Synthesis and biological activity of new class of dioxygenated anticancer agents. Curr Med Chem Anticancer Agents. 2005 May;5(3):215-37. Review. PubMed PMID: 15992351. 3: Kruczynski A, Barret JM, Van Hille B, Chansard N, Astruc J, Menon Y, Duchier C, Créancier L, Hill BT. Decreased nucleotide excision repair activity and alterations of topoisomerase IIalpha are associated with the in vivo resistance of a P388 leukemia subline to F11782, a novel catalytic inhibitor of topoisomerases I and II. Clin Cancer Res. 2004 May 1;10(9):3156-68. PubMed PMID: 15131057. 4: Jensen LH, Renodon-Cornière A, Nitiss KC, Hill BT, Nitiss JL, Jensen PB, Sehested M. A dual mechanism of action of the anticancer agent F 11782 on human topoisomerase II alpha. Biochem Pharmacol. 2003 Aug 15;66(4):623-31. PubMed PMID: 12906927. 5: Sargent JM, Elgie AW, Williamson CJ, Hill BT. Ex vivo effects of the dual topoisomerase inhibitor tafluposide (F 11782) on cells isolated from fresh tumor samples taken from patients with cancer. Anticancer Drugs. 2003 Jul;14(6):467-73. PubMed PMID: 12853890. 6: Etiévant C, Kruczynski A, Barret JM, Perrin D, Hill BT. Apoptotic cell death induction by F 11782 a novel dual catalytic inhibitor of topoisomerases I and II. Biochem Pharmacol. 2003 Mar 1;65(5):755-63. PubMed PMID: 12628489. 7: Denny WA, Baguley BC. Dual topoisomerase I/II inhibitors in cancer therapy. Curr Top Med Chem. 2003;3(3):339-53. Review. PubMed PMID: 12570767. 8: Kruczynski A, Ricome C, Waud WR, Hill BT. In vivo antitumor activity of F 11782, a non-intercalating dual catalytic inhibitor of topoisomerases I and II, against a panel of human tumor xenografts. J Exp Ther Oncol. 2002 Jul-Aug;2(4):219-27. PubMed PMID: 12416026. 9: Barret JM, Kruczynski A, Etiévant C, Hill BT. Synergistic effects of F 11782, a novel dual inhibitor of topoisomerases I and II, in combination with other anticancer agents. Cancer Chemother Pharmacol. 2002 Jun;49(6):479-86. PubMed PMID: 12107553. 10: Barret JM, Etiévant C, Baudouin C, Skov K, Charvéron M, Hill BT. F 11782, a novel catalytic inhibitor of topoisomerases I and II, induces atypical, yet cytotoxic DNA double-strand breaks in CHO-K1 cells. Anticancer Res. 2002 Jan-Feb;22(1A):187-92. PubMed PMID: 12017285. 11: Barret JM, Cadou M, Hill BT. Inhibition of nucleotide excision repair and sensitisation of cells to DNA cross-linking anticancer drugs by F 11782, a novel fluorinated epipodophylloid. Biochem Pharmacol. 2002 Jan 15;63(2):251-8. PubMed PMID: 11841800. 12: Barret JM, Montaudon D, Etiévant C, Perrin D, Kruczynski A, Robert J, Hill BT. Detection of DNA-strand breaks in cells treated with F 11782, a catalytic inhibitor of topoisomerases I and II. Anticancer Res. 2000 Nov-Dec;20(6B):4557-62. PubMed PMID: 11205304. 13: van Hille B, Etiévant C, Barret JM, Kruczynski A, Hill BT. Characterization of the biological and biochemical activities of F 11782 and the bisdioxopiperazines, ICRF-187 and ICRF-193, two types of topoisomerase II catalytic inhibitors with distinctive mechanisms of action. Anticancer Drugs. 2000 Nov;11(10):829-41. PubMed PMID: 11142691. 14: Barret JM, Hill BT, Olive PL. Characterization of DNA-strand breakage induced in V79 cells by F 11782, a catalytic inhibitor of topoisomerases. Br J Cancer. 2000 Dec;83(12):1740-6. PubMed PMID: 11104575; PubMed Central PMCID: PMC2363439. 15: Kruczynski A, Etiévant C, Perrin D, Imbert T, Colpaert F, Hill BT. Preclinical antitumour activity of F 11782, a novel dual catalytic inhibitor of topoisomerases. Br J Cancer. 2000 Dec;83(11):1516-24. PubMed PMID: 11076662; PubMed Central PMCID: PMC2363411. 16: Etiévant C, Kruczynski A, Barret JM, Perrin D, van Hille B, Guminski Y, Hill BT. F 11782, a dual inhibitor of topoisomerases I and II with an original mechanism of action in vitro, and markedly superior in vivo antitumour activity, relative to three other dual topoisomerase inhibitors, intoplicin, aclarubicin and TAS-103. Cancer Chemother Pharmacol. 2000;46(2):101-13. PubMed PMID: 10972479. 17: Perrin D, van Hille B, Barret JM, Kruczynski A, Etiévant C, Imbert T, Hill BT. F 11782, a novel epipodophylloid non-intercalating dual catalytic inhibitor of topoisomerases I and II with an original mechanism of action. Biochem Pharmacol. 2000 Apr 1;59(7):807-19. PubMed PMID: 10718339.