FSL0680

Structure

• InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)
• InChIKey=WZNJWVWKTVETCG-UHFFFAOYSA-N

Synonyms

• 500-44-7
• L(-)-Mimosine
• L-Mimosine from Koa hoale seeds

Origin

Leucaena leucocephala
Mimosa pudica

Biological activities

Inhibition of DNA replication and cell cycle arrest at G1

Therapeutic

DNA synthesis inhibitor

Target

Iron/zinc chelation
Serine methyltransferase
Deoxyhypusyl hydroxylase

Assay information

Cell growth inhibition of lung cancer cells by 40-60% at 400 μM
Cell growth inhibition of brest cancer cells by more than 90% at 400 μM
Inhibition of the transcription of the cytoplasmic serine hydroxymethyltransferase gene (SHMT1)
Inhibition of deoxyhypusyl hydroxylase (50 μM)
Inhibition of tyrosinase (IC₅₀=3.68 μM)
Inhibition of the binding of Ctf4 to chromatin

References

• Park SY, Im JS, Park SR, Kim SE, Wang HJ, Lee JK
  Mimosine arrests the cell cycle prior to the onset of DNA replication by preventing the binding of human Ctf4/And-1 to chromatin via Hif-1? activation in HeLa cells.
  Cell Cycle, 11(4): 761-766 (2012)  22374673  doi: 10.4161/cc.11.4.19209
• Casañola-Martín GM, Marrero-Ponce Y, Khan MT, Ather A, Sultan S, Torrens F, Rotondo R
  TOMOCOMD-CARDD descriptors-based virtual screening of tyrosinase inhibitors: evaluation of different classification model combinations using bond-based linear indices.
  Bioorg Med Chem, 15(3): 1483-1503 (2007)  17110117  doi: 10.1016/j.bmc.2006.10.067
• Perry C, Sastry R, Nasrallah IM, Stover PJ
  Mimosine attenuates serine hydroxymethyltransferase transcription by chelating zinc. Implications for inhibition of DNA replication.
  J Biol Chem, 280(1): 396-400 (2005)  15531579  doi: 10.1074/jbc.M410467200
• Chang HC, Lee TH, Chuang LY, Yen MH, Hung WC
  Inhibitory effect of mimosine on proliferation of human lung cancer cells is mediated by multiple mechanisms.
  Cancer Lett, 145(1-2): 1-8 (1999)  10530763
• Kulp KS, Vulliet PR
  Mimosine blocks cell cycle progression by chelating iron in asynchronous human breast cancer cells.
  Toxicol Appl Pharmacol, 139(2): 356-364 (1996)  8806853  doi: 10.1006/taap.1996.0176
• Lin HB, Falchetto R, Mosca PJ, Shabanowitz J, Hunt DF, Hamlin JL
  Mimosine targets serine hydroxymethyltransferase.
  J Biol Chem, 271(5): 2548-2556 (1996)  8576220
• Hanauske-Abel HM, Park MH, Hanauske AR, Popowicz AM, Lalande M, Folk JE
  Inhibition of the G1-S transition of the cell cycle by inhibitors of deoxyhypusine hydroxylation.
  Biochim Biophys Acta, 1221(2): 115-124 (1994)  8148388
• Thompson JF, Morris CJ, Smith IK
  New naturally occurring amino acids.
  Annu Rev Biochem, 38: 137-158 (1969)  4897064  doi: 10.1146/annurev.bi.38.070169.001033