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Chemical Compound Review

DA-125     [2-[(2R,4S)-4- [(2S,3R,4R,5S,6S)-3-fluoro- 4...

Synonyms: SureCN4849040, AC1L3FWQ, LS-16020, DA 125, 140637-82-7, ...
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Disease relevance of 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester

 

High impact information on 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester

 

Chemical compound and disease context of 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester

  • PURPOSE: DA-125 is a novel anthracycline derivative developed by Dong-A Pharmaceutical Company, Korea. Preclinical studies have suggested that DA-125 has greater efficacy and less toxicity than doxorubicin [2].
 

Biological context of 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester

  • DA-125-induced apoptosis was also decreased in JNK1- -transfected cells [4].
  • In the MTT test, DA-125 showed lower IC50 values than doxorubicin for 14 of 20 cell lines [5].
  • Pharmacokinetics of four metabolites of DA-125, a new anthracycline antineoplastic agent after single and multiple intravenous administration to rats [6].
  • The tissue distribution, and biliary and urinary excretion of four metabolites (M1-M4) of a new anthracycline antineoplastic agent (DA-125) were compared after single and multiple (7 consecutive days) intravenous (i.v.) administration to rats [6].
  • DA-125 was given at dose levels of 0, 0.1, 0.3, and 1.0 mg/kg/day administered intravenously to pregnant rats from days 7 to 17 of gestation [7].
 

Anatomical context of 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester

  • Cellular uptake and antitumor activity of the new anthracycline analog DA-125 in human cancer cell lines [5].
  • The maximally tolerated dose (MTD) of DA-125 was determined to be 100 mg/m2, and the dose-limiting factor for DA-125 was bone marrow suppression [3].
  • Mean AUAts (area under the amount-time curves from time zero to last measurement time t) (or AUCts-area under the plasma concentration-time curves from time zero until the last measurement time t) of M1-M4 in each tissue after single and multiple administrations of DA-125 were also comparable except in the bone marrow and thymus [6].
 

Associations of 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester with other chemical compounds

  • Among cancer cells from the stomach and colon, DA-125 was more potent than doxorubicin in 12 of 14 cell lines [5].
  • The pharmacokinetics of M1, M2, M3 and/or M4 were compared after intravenous (i.v.) administration of DA-125 and/or ME2303 to mice (25 mg kg(-1)) and rats (5, 10, 20, 30, and 40 mg kg(-1)) [8].
 

Gene context of 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester

  • In all lines tested, the mean IC50 values for both DA-125 and ADM were lowest in the parent cells, followed by CDDP-resistant cells and ADM-resistant cells [9].
 

Analytical, diagnostic and therapeutic context of 3-aminopropanoic acid [2-[(2S,4S)-4-[(2S,3R,4R,5R,6S)-3-fluoro-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxo-ethyl] ester

References

  1. Inhibitory effect of DA-125, a new anthracyclin analog antitumor agent, on the invasion of human fibrosarcoma cells by down-regulating the matrix metalloproteinases. Park, H.J., Chung, H.J., Min, H.Y., Park, E.J., Hong, J.Y., Kim, W.B., Kim, S.H., Lee, S.K. Biochem. Pharmacol. (2005) [Pubmed]
  2. A phase II trial of DA-125, a novel anthracycline, in advanced non-small-cell lung cancer. Kang, Y.K., Ryoo, B.Y., Kim, T.Y., Im, Y.H., Kim, B.S., Park, Y.H., Lee, C.T. Cancer Chemother. Pharmacol. (1999) [Pubmed]
  3. Phase I clinical trial: pharmacokinetics of a novel anthracycline, DA-125 and metabolites. Single dose study. Roh, J.K., Rha, S.Y., Lee, C.I., Lee, K.H., Lee, J.J., Shim, H.J., Lee, S.D., Kim, W.B., Yang, J., Kim, S.H., Lee, M.G. International journal of clinical pharmacology and therapeutics. (1998) [Pubmed]
  4. DA-125, a novel anthracycline derivative showing high-affinity DNA binding and topoisomerase II inhibitory activities, exerts cytotoxicity via c-Jun N-terminal kinase pathway. Kim, S.G., Sung, M., Kang, K.W., Kim, S.H., Son, M.H., Kim, W.B. Cancer Chemother. Pharmacol. (2001) [Pubmed]
  5. Cellular uptake and antitumor activity of the new anthracycline analog DA-125 in human cancer cell lines. Lim, K.H., Kim, H.S., Yang, Y.M., Lee, S.D., Kim, W.B., Yang, J., Park, J.G. Cancer Chemother. Pharmacol. (1997) [Pubmed]
  6. Pharmacokinetics of four metabolites of DA-125, a new anthracycline antineoplastic agent after single and multiple intravenous administration to rats. Lee, S.D., Lee, W.I., Shim, H.J., Lee, E.D., Kim, W.B., Yang, J., Kim, C.K., Lee, M.G. Journal of clinical pharmacy and therapeutics. (1996) [Pubmed]
  7. Teratogenic effects of DA-125, a new anthracycline anticancer agent, in rats. Chung, M.K., Kim, J.C., Roh, J.K. Reprod. Toxicol. (1995) [Pubmed]
  8. Comparison of pharmacokinetics of M1, M2, M3, and M4 after intravenous administration of DA-125 or ME2303 to mice and rats. New adriamycin analogues containing fluorine. Yoon, E.J., Lee, W.I., Shim, H.J., Lee, S.D., Kim, W.B., Yang, J., Lee, M.G. Biopharmaceutics & drug disposition. (1996) [Pubmed]
  9. Antitumor activity of DA-125, a novel anthracycline, in human gastric and pulmonary adenocarcinoma cells resistant to adriamycin and cisplatin. Hong, W.S., Jung, H.Y., Yang, S.K., Kim, H.R., Min, Y.I. Anticancer Res. (1997) [Pubmed]
  10. Simultaneous determination of a new anthracycline, DA-125, and its metabolites M1, M2, M3 and M4 in plasma and urine by high-performance liquid chromatography. Shim, H.J., Lee, E.D., Yoon, E.J., Lee, S.D., Kim, W.B., Yang, J., Lee, M.G. J. Chromatogr. B, Biomed. Appl. (1994) [Pubmed]
 
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