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Chem Read Done

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Chemistry
School
University of Southern Indiana
Type
Homework
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Read the review article titled "Cisplatin Discovery, Chemistry, Cancer Action, and
Guidance" and answer the following questions in your own words:
1) Describe the structure of cisplatin. What are the common characteristics of the
cisplatin-like drug?
Cisplatin (CDDP, cis-diamino dichloro platin) is a platinum complex, with a planar
structure, consisting of two chlorine atoms that protrude in the cis position around the
platinum atom. The stereochemistry of this compound is essential for its therapeutic effects
since the trans isomer is not cytotoxic.
Complete bioavailability
Protein binding> 95%
Metabolism 56
Half-life 30-100 hours
When the chloride concentration is lower, cisplatin readily undergoes an exchange of
chloride ligand for water (H2O) ligand (s). The diamminediaquaPt (II) thus formed can
react with N bases by replacing water ligands with N-based ligands.
As such, cisplatin primarily binds to two guanine N atoms of double-stranded DNA and
thus induces programmed death. Since the trans configuration cannot do this, transplatin is
not effective in destroying DNA. Cisplatin is effective against many cancers, particularly in
combination chemotherapy with other anticancer drugs, such as Taxol and/or vinblastine.
However, cisplatin has serious cytotoxicities to healthy cells because cisplatin can destroy
DNA in healthy and cancer cells. Furthermore, Pt (II) has a high affinity for S-containing
ligands.
2) Cisplatin is most commonly prepared by a multi-step reaction from [PtCl4] 2
(Indian J. Chem. 1970, 8, 193). Draw the structure of the intermediate formed in
Scheme 1 with the appropriate stereochemistry.

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