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S-Trityl-L-cysteine

S-Trityl-L-cysteine (STLC) is an organosulfur compound found in garlic plants. STLC exhibits anticancer and potential chemotherapeutic activities across several models. STLC acts as a mitotic inhibitor, inhibiting mitotic kinesin Eg5 and preventing separation of duplicated chromosomes and formation of bipolar spindles during mitosis. In chronic myelogenous leukemia (CML) cells, STLC induces cleavage of poly(ADP)-ribose polymerase (PARP) and activation of caspase 3, resulting in apoptosis and cell death.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18971255

Cas No.

2799-07-7

Purity

≥98%

Formula

C22H21NO2S

Formula Wt.

363.47

Chemical Name

S-(Triphenylmethyl)-L-cysteine

IUPAC Name

(2R)-2-amino-3-tritylsulfanylpropanoic acid

Synonym

NSC83265

Appearance

White to off white powder

Abualhasan MN, Good JA, Wittayanarakul K, et al. Doing the methylene shuffle–further insights into the inhibition of mitotic kinesin Eg5 with S-trityl L-cysteine. Eur J Med Chem. 2012 Aug;54:483-98. PMID: 22749640.

Shimizu M, Ishii H, Ogo N, et al. S-trityl-L-cysteine derivative induces caspase-independent cell death in K562 human chronic myeloid leukemia cell line. Cancer Lett. 2010 Dec 1;298(1):99-106. PMID: 20619960.

Kozielski F, Skoufias DA, Indorato RL, et al. Proteome analysis of apoptosis signaling by S-trityl-L-cysteine, a potent reversible inhibitor of human mitotic kinesin Eg5. Proteomics. 2008 Jan;8(2):289-300. PMID: 18186019.

Skoufias DA, DeBonis S, Saoudi Y, et al. S-trityl-L-cysteine is a reversible, tight binding inhibitor of the human kinesin Eg5 that specifically blocks mitotic progression. J Biol Chem. 2006 Jun 30;281(26):17559-69. PMID: 16507573.

PF04691503