Excited state proton transfer in 9-aminoacridine carboxamides in water and in DNA
- Iowa State Univ., Ames, IA (United States)
The 9-aminoacridine molecule is important in several different fields of chemistry. The absorption and fluorescence spectra of this compound are pH sensitive and it is this property that allowed it to be used as a pH probe in different chemical environments. The compound exhibits proton transfer reactions which are among the most fundamental of chemical reactions. The planarity of 9-aminoacridine allows it to intercalate into DNA. Intercalation is a process in which the aromatic flat surface of the intercalator inserts between adjacent base pairs of DNA. The large surface area of 9-aminoacridine`s fused tricyclic ring system allows strong intercalative binding through van der Waals attractions. 9-aminoacridine and many of its derivatives have been tried as possible antitumor drugs. The cytotoxicity of an antitumor agent can be dramatically increased through the addition of one or two cationic side chains. This increase in cytotoxicity using the 9-aminoacridine compound as a parent molecule has been investigated through various derivatives with cationic side chains consisting of different number of carbon atoms between the proximal and distal N atoms. Similar derivatives varied the position of the carboxamide side chain on the aromatic ring system. The objective of this work is to first create a baseline study of the excited state kinetics of the 9-aminoacridine carboxamides in the absence of DNA. The baseline study will allow the excited state kinetics of these antitumor drugs when placed in DNA to be more fully understood.
- Research Organization:
- Ames Lab., Ames, IA (United States)
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- W-7405-ENG-82
- OSTI ID:
- 130623
- Report Number(s):
- IS-T-1757; ON: DE96002243; TRN: 95:008297
- Resource Relation:
- Other Information: TH: Thesis (Ph.D.); PBD: 1995
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
DNA
CHEMICAL REACTIONS
NEOPLASMS
DRUGS
ACRIDINES
FLUORESCENCE
SURFACE AREA
SPECTRA
ABSORPTION
CLATHRATES
EXCITED STATES
POTENTIAL ENERGY
ALGORITHMS
BIOCHEMISTRY
MATHEMATICAL MODELS
VAN DER WAALS FORCES
CHEMICAL BONDS