WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406186
CAS#: 142439-61-0
Description: SN-23862 is a bioreductive agent with potential anticancer activity. SN-23862 is analogue of CB-1954, a dinitrobenzamide aziridine with nitrogen mustard. SN-23862 is also a prodrug that is activated by enzymatic nitroreduction in tumor.
MedKoo Cat#: 406186
Name: SN-23862
CAS#: 142439-61-0
Chemical Formula: C11H12Cl2N4O5
Exact Mass: 350.01847
Molecular Weight: 351.14278
Elemental Analysis: C, 37.63; H, 3.44; Cl, 20.19; N, 15.96; O, 22.78
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Synonym: SN23862; SN23862; SN 23862
IUPAC/Chemical Name: 5-(N, N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
InChi Key: DQMALWRRERBILB-UHFFFAOYSA-N
InChi Code: InChI=1S/C11H12Cl2N4O5/c12-1-3-15(4-2-13)9-5-7(11(14)18)8(16(19)20)6-10(9)17(21)22/h5-6H,1-4H2,(H2,14,18)
SMILES Code: O=C(N)C1=CC(N(CCCl)CCCl)=C([N+]([O-])=O)C=C1[N+]([O-])=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
The following data is based on the product molecular weight 351.14278 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: Çelik A, Yetiş G. An unusually cold active nitroreductase for prodrug activations. Bioorg Med Chem. 2012 Jun 1;20(11):3540-50. doi: 10.1016/j.bmc.2012.04.004. Epub 2012 Apr 11. PubMed PMID: 22546205.
2: Wilson WR, Hicks KO, Pullen SM, Ferry DM, Helsby NA, Patterson AV. Bystander effects of bioreductive drugs: potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards. Radiat Res. 2007 Jun;167(6):625-36. PubMed PMID: 17523848.
3: Helsby NA, Ferry DM, Patterson AV, Pullen SM, Wilson WR. 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT. Br J Cancer. 2004 Mar 8;90(5):1084-92. PubMed PMID: 14997211; PubMed Central PMCID: PMC2409616.
4: Johansson E, Parkinson GN, Denny WA, Neidle S. Studies on the nitroreductase prodrug-activating system. Crystal structures of complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs and of the enzyme active form. J Med Chem. 2003 Sep 11;46(19):4009-20. PubMed PMID: 12954054.
5: Helsby NA, Wheeler SJ, Pruijn FB, Palmer BD, Yang S, Denny WA, Wilson WR. Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: distinct mechanisms of bioreductive activation. Chem Res Toxicol. 2003 Apr;16(4):469-78. PubMed PMID: 12703963.
6: Denny WA. Nitroreductase-based GDEPT. Curr Pharm Des. 2002;8(15):1349-61. Review. PubMed PMID: 12052212.
7: Wilson WR, Pullen SM, Hogg A, Helsby NA, Hicks KO, Denny WA. Quantitation of bystander effects in nitroreductase suicide gene therapy using three-dimensional cell cultures. Cancer Res. 2002 Mar 1;62(5):1425-32. PubMed PMID: 11888915.
8: Anlezark GM, Vaughan T, Fashola-Stone E, Michael NP, Murdoch H, Sims MA, Stubbs S, Wigley S, Minton NP. Bacillus amyloliquefaciens orthologue of Bacillus subtilis ywrO encodes a nitroreductase enzyme which activates the prodrug CB 1954. Microbiology. 2002 Jan;148(Pt 1):297-306. PubMed PMID: 11782522.
9: Kestell P, Pruijn FB, Siim BG, Palmer BD, Wilson WR. Pharmacokinetics and metabolism of the nitrogen mustard bioreductive drug 5. Cancer Chemother Pharmacol. 2000;46(5):365-74. PubMed PMID: 11127940.
10: Lee HH, Palmer BD, Wilson WR, Denny WA. Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard. Bioorg Med Chem Lett. 1998 Jul 7;8(13):1741-4. PubMed PMID: 9873426.
11: Atwell GJ, Boyd M, Palmer BD, Anderson RF, Pullen SM, Wilson WR, Denny WA. Synthesis and evaluation of 4-substituted analogues of 5-[N,N-bis (2-chloroethyl)amino]-2-nitrobenzamide as bioreductively activated prodrugs using an Escherichia coli nitroreductase. Anticancer Drug Des. 1996 Oct;11(7):553-67. PubMed PMID: 8921936.
12: Palmer BD, Wilson WR, Anderson RF, Boyd M, Denny WA. Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide. J Med Chem. 1996 Jun 21;39(13):2518-28. PubMed PMID: 8691449.
13: Wilson WR, Pruijn FB. Hypoxia-activated prodrugs as antitumour agents: strategies for maximizing tumour cell killing. Clin Exp Pharmacol Physiol. 1995 Nov;22(11):881-5. PubMed PMID: 8593750.
14: Anlezark GM, Melton RG, Sherwood RF, Wilson WR, Denny WA, Palmer BD, Knox RJ, Friedlos F, Williams A. Bioactivation of dinitrobenzamide mustards by an E. coli B nitroreductase. Biochem Pharmacol. 1995 Aug 25;50(5):609-18. PubMed PMID: 7669063.
15: Palmer BD, van Zijl P, Denny WA, Wilson WR. Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide. J Med Chem. 1995 Mar 31;38(7):1229-41. PubMed PMID: 7707325.
16: Palmer BD, Wilson WR, Atwell GJ, Schultz D, Xu XZ, Denny WA. Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide. J Med Chem. 1994 Jul 8;37(14):2175-84. PubMed PMID: 8035424.
17: Cliffe S, Taylor ML, Rutland M, Baguley BC, Hill RP, Wilson WR. Combining bioreductive drugs (SR 4233 or SN 23862) with the vasoactive agents flavone acetic acid or 5,6-dimethylxanthenone acetic acid. Int J Radiat Oncol Biol Phys. 1994 May 15;29(2):373-7. PubMed PMID: 8195036.
18: Palmer BD, Wilson WR, Cliffe S, Denny WA. Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells. J Med Chem. 1992 Aug 21;35(17):3214-22. PubMed PMID: 1507207.
CB1954 and SN-23862 structures
CB1954 and SN-23862 structures
