2799-07-7

S-Trityl-cysteine (2799-07-7) is a cell permeable inhibitor of mitotic kinesin Eg5 (IC50 for inhibition of basal ATPase activity = 1 μM; IC50 for inhibition of microtubule-activated ATPase activity = 140 nM). Mean growth concentration (GI50) of 1.31 μM for a panel of 60 different tumor cell lines.

almost white to light yellow granular powder

A protected cysteine for peptide synthesis. S-Trityl-L-cysteine (STLC) is a tight-binding inhibitor of Eg5 that prevents mitotic progression. It has proven antitumor activity as shown in the NCI 60 tumor cell line screen.

A protected cysteine for peptide synthesis. S-Trityl-L-cysteine (STLC) is a tight-binding inhibitor of Eg5 that prevents mitotic progression. It has proven antitumor activity as shown in the NCI 60 tumor cell line screen.

ChEBI: (2R)-2-amino-3-[(triphenylmethyl)thio]propanoic acid is a benzenoid aromatic compound.

reaction type: solution phase peptide synthesis

Potent, cell-permeable, selective inhibitor of mitotic kinesin Eg5, a protein required for establishing and maintaining a bipolar spindle. Inhibits basal ATPase activity (IC 50 = 1 mM) and microtubule-activated ATPase activity of Eg5 (IC 50 = 140 nM). Induces mitotic arrest in HeLa cells with an IC 50 of 700 nM. Displays antitumor activity.

Triphenylmethanol (3.3 g, 12.7 mmol) and L-cysteine hydrochloride (2 g, 12.7 mmol) were reacted in 25 mL of trifluoroacetic acid (TFA). The mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C, followed by the slow addition of 4 N sodium hydroxide solution and ether (40 mL) to adjust the pH to 4-5. Next, 10% aqueous sodium acetate was added to further adjust the pH to 5-6. The precipitate precipitated from the reaction mixture was collected by filtration, washed with fresh ether, and dried to afford S-trityl-L-cysteine (5 g, 98% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 2.35-2.61 (m, 2H, CH2), 2.85-2.98 (m, 1H, CH), 7.2-7.45 (m, 15H, triphenylmethyl-L-H).MALDI-TOF MS analysis showed m/z 364.7 [M + H]+, which is in agreement with the theoretical C22H21NO2S molecular weight (363.47).

Store at +4°C

1) DeBonis et al. (2004) In vitro screening for inhibitors of the human mitotic kinesin Eg5 with antimitotic and antitumour activities; Mol. Cancer Ther. 3 1079 2) Brier et al. (2004) Identification of the protein binding region of S-trityl-L-cysteine, a new potent inhibitor of mitotic kinesin Eg5; Biochemistry 43 13072 3) Skoufias et al. (2006) S-trityl-l-cysteine is a reversible, tight-binding inhibitor of the human kinesin eg5 that specifically blocks mitotic progression; J. Biol. Chem., 281 17559