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Chemical Compound Review

CHEMBL281812     5-[bis(2-chloroethyl)amino]- 2,4-dinitro...

Synonyms: ACMC-1C65P, AG-D-84048, CHEBI:126457, NSC-646392, SN-23862, ...
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Disease relevance of NSC646392

  • Therefore, a series of compounds related to SN 23862 has been synthesized, and evaluated as potential prodrugs both by determination of kinetic parameters and by ratio of IC50 against UV4 cells when incubated in the presence of prodrug, with and without the E. coli enzyme and cofactor (NADH) [1].

High impact information on NSC646392

  • In contrast, the larger mustard group of the dinitrobenzamide mustard compound SN 23862 forces the prodrug to bind at both active sites with only the 2-nitro group able to participate in hydride transfer from the FMN, explaining why only the 2-hydroxylamine reduction product is observed [2].
  • The related mustard SN 23862 has similar selectivity and superior bystander effects in animal models [3].
  • A nitroreductase isolated and purified from Escherichia coli B has been demonstrated to have potential applications in ADEPT (antibody-directed enzyme prodrug therapy) by its ability in vitro to reduce dinitrobenzamides (e.g. 5-aziridinyl 2,4-dinitrobenzamide, CB 1954 and its bischloroethylamino analogue, SN 23862) to form cytotoxic derivatives [1].
  • PURPOSE: To characterise the pharmacokinetics and metabolism in mice of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862), the lead compound of a new class of bioreductive drugs in which a nitrogen mustard is activated by nitroreduction [4].
  • 2,4-Dinitrobenzamide mustards, exemplified by the parent compound SN 23862 (2) are activated under aerobic conditions by an Escherichia coli nitroreductase enzyme (NR2) via selective reduction of the 2-nitro group, and are thus of interest as prodrugs for antibody-directed enzyme-prodrug therapy (ADEPT) [5].

Analytical, diagnostic and therapeutic context of NSC646392

  • These results are consistent with the reported high bystander efficiency of SN 23862 as an NTR prodrug in multicellular layers and tumour xenografts [6].


  1. Bioactivation of dinitrobenzamide mustards by an E. coli B nitroreductase. Anlezark, G.M., Melton, R.G., Sherwood, R.F., Wilson, W.R., Denny, W.A., Palmer, B.D., Knox, R.J., Friedlos, F., Williams, A. Biochem. Pharmacol. (1995) [Pubmed]
  2. Studies on the nitroreductase prodrug-activating system. Crystal structures of complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs and of the enzyme active form. Johansson, E., Parkinson, G.N., Denny, W.A., Neidle, S. J. Med. Chem. (2003) [Pubmed]
  3. Nitroreductase-based GDEPT. Denny, W.A. Curr. Pharm. Des. (2002) [Pubmed]
  4. Pharmacokinetics and metabolism of the nitrogen mustard bioreductive drug 5. Kestell, P., Pruijn, F.B., Siim, B.G., Palmer, B.D., Wilson, W.R. Cancer Chemother. Pharmacol. (2000) [Pubmed]
  5. 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. Atwell, G.J., Boyd, M., Palmer, B.D., Anderson, R.F., Pullen, S.M., Wilson, W.R., Denny, W.A. Anticancer Drug Des. (1996) [Pubmed]
  6. 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT. Helsby, N.A., Ferry, D.M., Patterson, A.V., Pullen, S.M., Wilson, W.R. Br. J. Cancer (2004) [Pubmed]
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