[Blueboard] Seminar on local synthesis of cancer drug

Nina Rosario L. Rojas, Ph.D. nrojas at ateneo.edu
Sat Apr 16 16:07:31 PHT 2005

The Chemistry Department invites members of the community to the first
lecture in the

Chemistry Department Seminar Series
Summer Term 2005

A Synthetic Method for the Local Production of Mitoxantrone: An
Anti-Cancer Drug

M.S. Chemistry Thesis by:  Maria Lorna Arao-de Leoz
Adviser:  Modesto T. Chua, Ph.D.

Winner, Outstanding Graduate Research 2005
School of Science and Engineering

18 April 2005
4:30 p.m.
Schmitt Hall CH 109


Mitoxantrone is a potent anti-cancer drug effective against prostate,
ovarian and breast cancer, solid tumors, acute myeloid and nonlymphocytic
leukemia, multiple sclerosis and Hodgkin's lymphoma.  It is comparable in
clinical efficacy to other anthracyclines such as adriamycin but with
lesser toxic side effects.  However, this out-of-patent drug is currently
tagged at a high price in the United States.

This study aims to develop a synthetic procedure for mitoxantrone that can
be adapted for the local production of the drug.  Mitoxantrone was
originally prepared by subjecting an anthraquinone, chrysazin, to a
series of steps:  1) nitration, 2) reduction with iron powder, 3)
treatment with sodium hydrosulfite in basic solution followed by in situ
hydrolysis, and 4) one-pot treatment of the resultant intermediate with
an amino alcohol and a final oxidation step.  In the course of the study,
however, it was observed that there was a need for additional purification
steps of the nitration intermediate using sodium sulfite, followed by
sodium bicarbonate.  The reduction with iron powder also resulted in
incompletely reduced products.  An alternative route to the second step
was established which makes use of tin (II) chloride, followed by sodium
bicarbonate purification. Some parameters of the last two steps were also
modified.  The structure of the product was assigned on the basis of
spectral data and its cytotoxicity assay against breast cancer cells was

Nina Rosario L. Rojas, Ph.D.
Associate Professor
Chair, Department of Chemistry
Ateneo de Manila University
School of Science and Engineering
Loyola Heights, Quezon City
1108 Philippines
Telefax: +63-2-426-1323
Phone: +63-2-426-6001 x5620
nrojas at ateneo.edu

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