DNA-Interactive Drugs: Tomamycin


 
Name Tomamycin
NCS# 177499
Category Pyrrolo-(1,4)-benzodiazepine
Binding Mode Covalent adduction to N2-G in DNA minor groove; aromatic ring oriented to the 3' side of the adduct, also in minor groove [Boyd, 1990].
Site Specificity 5'-RGR-3' > 5'-RGY-3' > 5'-YGR-3' > 5'-YGY-3'  [Hertzberg, 1986; Hurley, 1988]
Effect on DNA Aromatic group of tomamycin is positioned to the 3' side of the covalent adduct in one NMR solution study.  Overall helical distortion is minimal [Boyd, 1990].  Depending on sequence, bends DNA 8.25o to 14o [Kizu, 1993].
Source Originally isolated from Streptomyces achromogenes var. tomaymyceticus [Arima, 1972].
Preparation and Use Dissolved in DMSO to stock concentration of 10mM.  In methanol, extinction coefficient at 320nm is 3600 M-1 cm-1 [Arima, 1972].
 
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Please direct all comments to: Jack Welch, M.D., Ph.D.
Last Modified August 1, 1998Last modification: August 10, 1998