WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H524769
CAS#: 136440-70-5
Description: CP 115953 inhibits topoisomerase II activity via an interaction with the enzyme and not by DNA unwinding. CP 115953 stimulates cytokine production by lymphocytes.
Hodoodo Cat#: H524769
Name: CP 115953
CAS#: 136440-70-5
Chemical Formula: C19H13F2NO4
Exact Mass: 357.08
Molecular Weight: 357.310
Elemental Analysis: C, 63.87; H, 3.67; F, 10.63; N, 3.92; O, 17.91
This product is not in stock, which may be available by custom synthesis.
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Synonym: CP-115953; CP 115953; CP115953; Cp-115,953.
IUPAC/Chemical Name: 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxyphenyl)-4-oxo-3-quinolinecarboxylic acid
InChi Key: ISQTYKAFNUVODK-UHFFFAOYSA-N
InChi Code: InChI=1S/C19H13F2NO4/c20-14-7-12-17(16(21)15(14)9-1-5-11(23)6-2-9)22(10-3-4-10)8-13(18(12)24)19(25)26/h1-2,5-8,10,23H,3-4H2,(H,25,26)
SMILES Code: c1cc(ccc1c2c(cc3c(c2F)n(cc(c3=O)C(=O)O)C4CC4)F)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: >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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 357.31 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: Bromberg KD, Burgin AB, Osheroff N. Quinolone action against human topoisomerase IIalpha: stimulation of enzyme-mediated double-stranded DNA cleavage. Biochemistry. 2003 Apr 1;42(12):3393-8. PubMed PMID: 12653542.
2: Strumberg D, Nitiss JL, Dong J, Walker J, Nicklaus MC, Kohn KW, Heddle JG, Maxwell A, Seeber S, Pommier Y. Importance of the fourth alpha-helix within the CAP homology domain of type II topoisomerase for DNA cleavage site recognition and quinolone action. Antimicrob Agents Chemother. 2002 Sep;46(9):2735-46. PubMed PMID: 12183223; PubMed Central PMCID: PMC127396.
3: Dong J, Walker J, Nitiss JL. A mutation in yeast topoisomerase II that confers hypersensitivity to multiple classes of topoisomerase II poisons. J Biol Chem. 2000 Mar 17;275(11):7980-7. PubMed PMID: 10713116.
4: Anderson VE, Zaniewski RP, Kaczmarek FS, Gootz TD, Osheroff N. Quinolones inhibit DNA religation mediated by Staphylococcus aureus topoisomerase IV. Changes in drug mechanism across evolutionary boundaries. J Biol Chem. 1999 Dec 10;274(50):35927-32. PubMed PMID: 10585479.
5: Borde V, Duguet M. DNA topoisomerase II sites in the histone H4 gene during the highly synchronous cell cycle of Physarum polycephalum. Nucleic Acids Res. 1998 May 1;26(9):2042-49. Erratum in: Nucleic Acids Res 1998 Oct 15;26(20):following 4789. PubMed PMID: 9547257; PubMed Central PMCID: PMC147523.
6: Elsea SH, Westergaard M, Burden DA, Lomenick JP, Osheroff N. Quinolones share a common interaction domain on topoisomerase II with other DNA cleavage-enhancing antineoplastic drugs. Biochemistry. 1997 Mar 11;36(10):2919-24. PubMed PMID: 9062121.
7: Borde V, Duguet M. In vivo topoisomerase II cleavage sites in the ribosomal DNA of Physarum polycephalum. Biochemistry. 1996 May 7;35(18):5787-95. PubMed PMID: 8639539.
8: Hsiung Y, Elsea SH, Osheroff N, Nitiss JL. A mutation in yeast TOP2 homologous to a quinolone-resistant mutation in bacteria. Mutation of the amino acid homologous to Ser83 of Escherichia coli gyrA alters sensitivity to eukaryotic topoisomerase inhibitors. J Biol Chem. 1995 Sep 1;270(35):20359-64. PubMed PMID: 7657608.
9: Spitzner JR, Chung IK, Gootz TD, McGuirk PR, Muller MT. Analysis of eukaryotic topoisomerase II cleavage sites in the presence of the quinolone CP-115,953 reveals drug-dependent and -independent recognition elements. Mol Pharmacol. 1995 Aug;48(2):238-49. PubMed PMID: 7651357.
10: Riesbeck K, Forsgren A. CP-115,953 stimulates cytokine production by lymphocytes. Antimicrob Agents Chemother. 1995 Feb;39(2):476-83. PubMed PMID: 7726518; PubMed Central PMCID: PMC162563.
11: Elsea SH, Hsiung Y, Nitiss JL, Osheroff N. A yeast type II topoisomerase selected for resistance to quinolones. Mutation of histidine 1012 to tyrosine confers resistance to nonintercalative drugs but hypersensitivity to ellipticine. J Biol Chem. 1995 Jan 27;270(4):1913-20. PubMed PMID: 7829529.
12: Osheroff N, Corbett AH, Elsea SH, Westergaard M. Defining functional drug-interaction domains on topoisomerase II by exploiting mechanistic differences between drug classes. Cancer Chemother Pharmacol. 1994;34 Suppl:S19-25. Review. PubMed PMID: 8070023.
13: Elsea SH, McGuirk PR, Gootz TD, Moynihan M, Osheroff N. Drug features that contribute to the activity of quinolones against mammalian topoisomerase II and cultured cells: correlation between enhancement of enzyme-mediated DNA cleavage in vitro and cytotoxic potential. Antimicrob Agents Chemother. 1993 Oct;37(10):2179-86. PubMed PMID: 8257142; PubMed Central PMCID: PMC192247.
14: Corbett AH, Hong D, Osheroff N. Exploiting mechanistic differences between drug classes to define functional drug interaction domains on topoisomerase II. Evidence that several diverse DNA cleavage-enhancing agents share a common site of action on the enzyme. J Biol Chem. 1993 Jul 5;268(19):14394-8. PubMed PMID: 8390992.
15: Robinson MJ, Corbett AH, Osheroff N. Effects of topoisomerase II-targeted drugs on enzyme-mediated DNA cleavage and ATP hydrolysis: evidence for distinct drug interaction domains on topoisomerase II. Biochemistry. 1993 Apr 13;32(14):3638-43. PubMed PMID: 8385484.
16: Elsea SH, Osheroff N, Nitiss JL. Cytotoxicity of quinolones toward eukaryotic cells. Identification of topoisomerase II as the primary cellular target for the quinolone CP-115,953 in yeast. J Biol Chem. 1992 Jul 5;267(19):13150-3. PubMed PMID: 1320012.
17: Robinson MJ, Martin BA, Gootz TD, McGuirk PR, Osheroff N. Effects of novel fluoroquinolones on the catalytic activities of eukaryotic topoisomerase II: Influence of the C-8 fluorine group. Antimicrob Agents Chemother. 1992 Apr;36(4):751-6. PubMed PMID: 1323952; PubMed Central PMCID: PMC189387.
18: Robinson MJ, Martin BA, Gootz TD, McGuirk PR, Moynihan M, Sutcliffe JA, Osheroff N. Effects of quinolone derivatives on eukaryotic topoisomerase II. A novel mechanism for enhancement of enzyme-mediated DNA cleavage. J Biol Chem. 1991 Aug 5;266(22):14585-92. PubMed PMID: 1650363.
