WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H205828
CAS#: 220998-10-7 (free base)
Description: Elomotecan (BN-80927) belongs to a novel family of camptothecin analogs, the homocamptothecins, developed on the concept of topoisomerase I (Topo I) inhibition and characterized by a stable seven-membered beta-hydroxylactone ring. Preclinical data reported here show that BN80927 retains Topo I poisoning activity in cell-free assay (DNA relaxation) as well as in living cells, in which in vivo complexes of topoisomerase experiments and quantification of DNA-protein-complexes stabilization, have confirmed the higher potency of BN80927 as compared with the Topo I inhibitor SN38. In addition, BN80927 inhibits Topo II-mediated DNA relaxation in vitro but without cleavable-complex stabilization, thus indicating catalytic inhibition. Moreover, a Topo I-altered cell line (KBSTP2), resistant to SN38, remains sensitive to BN80927, suggesting that a part of the antiproliferative effects of BN80927 are mediated by a Topo I-independent pathway. This hypothesis is also supported by in vitro data showing an antiproliferative activity of BN80927 on a model of resistance related to the noncycling state of cells (G(0)-G(1) synchronized). In cell growth assays, BN80927 is a very potent antiproliferative agent as shown by IC(50) values consistently lower than those of SN38 in tumor cell lines as well as in their related drug-resistant lines. BN80927 shows high efficiency in vivo in tumor xenograft studies using human androgen-independent prostate tumors PC3 and DU145. Altogether, these data strongly support the clinical development of BN80927. (Source: Cancer Res. 2004 Jul 15;64(14):4942-9).
Hodoodo Cat#: H205828
Name: Elomotecan
CAS#: 220998-10-7 (free base)
Chemical Formula: C29H32ClN3O4
Exact Mass: 521.21
Molecular Weight: 522.035
Elemental Analysis: C, 66.72; H, 6.18; Cl, 6.79; N, 8.05; O, 12.26
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Related CAS #: 220997-99-9 (HCl) 220998-10-7 (free base),
Synonym: Elomotecan; BN80927; BN 80927; BN-80927; R1559; R-1559; R 1559;
IUPAC/Chemical Name: (R)-9-chloro-5-ethyl-5-hydroxy-10-methyl-12-((4-methylpiperidin-1-yl)methyl)-4,5-dihydrooxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15(1H,13H)-dione
InChi Key: KAQREZSTQZWNAG-GDLZYMKVSA-N
InChi Code: InChI=1S/C29H32ClN3O4/c1-4-29(36)12-26(34)37-15-21-22(29)10-25-27-20(14-33(25)28(21)35)19(13-32-7-5-16(2)6-8-32)18-9-17(3)23(30)11-24(18)31-27/h9-11,16,36H,4-8,12-15H2,1-3H3/t29-/m1/s1
SMILES Code: O=C(OC1)C[C@](O)(CC)C2=C1C(N3CC4=C(CN5CCC(C)CC5)C6=CC(C)=C(Cl)C=C6N=C4C3=C2)=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: >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:
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| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 522.04 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Yang S, Zhang WN. [Homocamptothecins--novel promising anticancer drugs as inhibitors of topoisomerase I]. Yao Xue Xue Bao. 2004 May;39(5):396-400. Review. Chinese. PubMed PMID: 15338888.
2: Demarquay D, Huchet M, Coulomb H, Lesueur-Ginot L, Lavergne O, Camara J, Kasprzyk PG, Prévost G, Bigg DC. BN80927: a novel homocamptothecin that inhibits proliferation of human tumor cells in vitro and in vivo. Cancer Res. 2004 Jul 15;64(14):4942-9. PubMed PMID: 15256467.
3: 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.
4: Ulukan H, Swaan PW. Camptothecins: a review of their chemotherapeutic potential. Drugs. 2002;62(14):2039-57. Review. PubMed PMID: 12269849.
5: Huchet M, Demarquay D, Coulomb H, Kasprzyk P, Carlson M, Lauer J, Lavergne O, Bigg D. The dual topoisomerase inhibitor, BN 80927, is highly potent against cell proliferation and tumor growth. Ann N Y Acad Sci. 2000;922:303-5. PubMed PMID: 11193907.
6: Demarquay D, Coulomb H, Huchet M, Lesueur-Ginot L, Camara J, Lavergne O, Bigg D. The homocamptothecin, BN 80927, is a potent topoisomerase I poison and topoisomerase II catalytic inhibitor. Ann N Y Acad Sci. 2000;922:301-2. PubMed PMID: 11193906.
7: Lavergne O, Harnett J, Rolland A, Lanco C, Lesueur-Ginot L, Demarquay D, Huchet M, Coulomb H, Bigg DC. BN 80927: a novel homocamptothecin with inhibitory activities on both topoisomerase I and topoisomerase II. Bioorg Med Chem Lett. 1999 Sep 6;9(17):2599-602. PubMed PMID: 10498216.
