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Testosterone as a delivery vector for platinum(II) metallodrugs

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Huxley, Martin (2006) Testosterone as a delivery vector for platinum(II) metallodrugs. PhD thesis, University of Warwick.

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Official URL: http://webcat.warwick.ac.uk/record=b2222152~S15

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Abstract

A total of 6 steroidal ligands have been synthesised from simple starting materials using
Sonogashira coupling reactions. The ligands are based on testosterone substituted in the
l7a-position with ethnynyl-pyridine, ethnynyl-quinoline or ethnynyl-isoquinoline. A
range of platinum(II) complexes have been synthesised using these ligands of the type
trans- and cis- [Pt(NH3)2(L)(Cl][N03], where L is the steroidal ligand, alongside control
complexes containing simple aromatic amines for comparison. The addition of the steroid
imparted a substantional ability of the steroidal platinum(II) complexes to alter the
structure of B-DNA. Furthermore, the steroid imparted cytotoxicity onto the complexes,
which were very much more active that the steroidal ligand alone or platinum(II)
complexes containing only an aromatic amine. Moreover, forcing the steroidal skeleton
closer to DNA using 3-substituted pyridine rings and cis-geometries caused greater DNA
unwinding, which is likely to relate to direct interactions between the DNA helix and the
steroidal skeleton.

Item Type: Thesis or Dissertation (PhD)
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Library of Congress Subject Headings (LCSH): Ligands (Biochemistry), Steroids, Testosterone, Platinum compounds, Antineoplastic agents, DNA-ligand interactions
Official Date: September 2006
Dates:
DateEvent
September 2006Submitted
Institution: University of Warwick
Theses Department: Department of Chemistry
Thesis Type: PhD
Publication Status: Unpublished
Supervisor(s)/Advisor: Rodger, Alison ; Hannon, Mike
Extent: 352 p.
Language: eng

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