Caroline Descôteaux, Kevin Brasseur, Valérie Leblanc, Sophie Parent, Eric Asselin, Gervais Bérubé
Index: Steroids 77(5) , 403-12, (2012)
Full Text: HTML
L-para-Tyrosine was linked to ortho-hydroxyaniline, meta-hydroxyaniline and para-hydroxyaniline giving three distinct tyrosinamide molecules. The new extended amino acid derivatives were constructed to imitate, in part, the estradiol (E(2), the natural female sex hormone) nucleus. The resulting tyrosinamides were then linked to chlorambucil either directly, or via a 5 and 10 carbon atoms spacer chain. This was done in an attempt to target cancerous cells expressing the estrogen receptor alpha (ERα) and to obtain a more specific chemotherapeutic agent. The tyrosinamide-chlorambucil molecules were designed and synthesized in good yields, according to two different approaches. The novel compounds were evaluated for their anticancer efficacy in hormone-dependent and hormone-independent (ER+; MCF-7 and ER-; MDA-MB-231) breast cancer cell lines. Interestingly, the meta-hydroxyphenyl-tyrosinamide-chlorambucil derivatives were more active than the ortho- and para- analogs. The molecules bearing a 5 carbon atoms spacer were selected for additional biological study using a panel of female cancerous cells; breast (ZR-75-1, MDA-MB-436, MDA-MB-468), ovarian (OVCAR-3, A2780) and uterine (Ishikawa, HEC-1A). It was discovered that for breast cancer cells, the new compounds were up to 4.2 times more active than chlorambucil itself.Copyright © 2011 Elsevier Inc. All rights reserved.
Structure | Name/CAS No. | Molecular Formula | Articles |
---|---|---|---|
![]() |
H-Tyr-NH2
CAS:4985-46-0 |
C9H13ClN2O2 |
Solvent selection and optimization of α-chymotrypsin-catalyz...
2012-01-01 [Biotechnol. Prog. 28(6) , 1443-9, (2012)] |
Enzymatic copolymerization alters the structure of unpolymer...
2004-01-01 [Biomacromolecules 5(5) , 1869-76, (2004)] |
Derivatization and purification of bisecting tyrosinamide-ol...
1994-12-01 [Arch. Biochem. Biophys. 315(2) , 460-6, (1994)] |
Probing the binding specificity of C-type lectins in vivo.
2003-01-01 [Meth. Enzymol. 363 , 90-104, (2003)] |
Synthesis, spectroscopic and structural elucidation of tyros...
2009-02-01 [Amino Acids 36(2) , 195-201, (2009)] |
Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer
Copyright © 2024 ChemSrc All Rights Reserved