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Chemical Compound Review: 

AC1O5NJA     methyl6-[(E)-1- methoxycarbonylprop-1-en-2...

Synonyms: LS-56707, U 73975, 123219-86-3
 
 
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Disease relevance of U-73975

  • Although carzelesin was less potent in terms of in vitro cytotoxicity and in vivo optimal dosage and showed low affinity for binding to DNA, it was therapeutically more efficacious against mouse L1210 leukemia than was U-76074 or adozelesin (U-73975), another cyclopropylpyrroloindole analogue which is currently in phase I clinical trials [1].
  • Adozelesin (U-73975) is an extremely potent cytotoxic agent which causes 90% lethality, after 2 h exposure in vitro, of Chinese hamster ovary and lung (CHO and V79), mouse melanoma (B16), and human ovarian carcinoma (A2780) cells at 0.33, 0.19, 0.2, and 0.025 ng/ml, respectively [2].
  • The technique utilizes a modified form of bacteriophage T7 polymerase, Sequenase, to synthesize a radiolabeled nascent strand from dsDNA that has been reacted in vitro with the CC-1065 analogue U-73975 (adozelesin) [3].
 

High impact information on U-73975

  • Lethality, DNA alkylation, and cell cycle effects of adozelesin (U-73975) on rodent and human cells [2].
  • 1,2-Dihydro-1-(chloromethyl)-5-hydroxy-8-methyl-3H-furano[3,2-e]in dole (CFI) as a novel replacement of the cyclopropylpyrroloindoline (CPI) alkylation subunit of CC-1065, U-71184, and U-73975 (adozelesin) has been synthesized and incorporated into a series of efficacious antineoplastic agents [4].
  • This technique yielded a consensus sequence for U-73975 bonding that is similar to, but not identical with, the published consensus obtained for CC-1065 by a modified Maxam and Gilbert sequencing technique [3].

References

  1. Cytotoxicity and antitumor activity of carzelesin, a prodrug cyclopropylpyrroloindole analogue. Li, L.H., DeKoning, T.F., Kelly, R.C., Krueger, W.C., McGovren, J.P., Padbury, G.E., Petzold, G.L., Wallace, T.L., Ouding, R.J., Prairie, M.D. Cancer Res. (1992) [Pubmed]
  2. Lethality, DNA alkylation, and cell cycle effects of adozelesin (U-73975) on rodent and human cells. Bhuyan, B.K., Smith, K.S., Adams, E.G., Petzold, G.L., McGovren, J.P. Cancer Res. (1992) [Pubmed]
  3. In vitro and in vivo DNA bonding by the CC-1065 analogue U-73975. Weiland, K.L., Dooley, T.P. Biochemistry (1991) [Pubmed]
  4. Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: an asymmetric hydroboration mediated synthesis of the alkylation subunits. Mohamadi, F., Spees, M.M., Staten, G.S., Marder, P., Kipka, J.K., Johnson, D.A., Boger, D.L., Zarrinmayeh, H. J. Med. Chem. (1994) [Pubmed]
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