Tafluposide

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

MedKoo CAT#: 528413

CAS#: 179067-42-6

Description: 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.


Price and Availability

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Tafluposide (F-11782) is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 528413
Name: Tafluposide
CAS#: 179067-42-6
Chemical Formula: C45H35F10O20P
Exact Mass: 1116.13
Molecular Weight: 1116.7128
Elemental Analysis: C, 48.40; H, 3.16; F, 17.01; O, 28.65; P, 2.77


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]


Technical Data

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).

Harmonized System Code:
293490


References

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.