Tuning the DNA reactivity of cis-platinum: Conjugation to a mismatch-specific metallointercalator

Journal of the American Chemical Society

Volumn 126, Issue 45, 2004, Pages 14728-14729

  Petitjean, Anne ^a   Barton, Jacqueline K ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; DNA; INTERCALATING AGENT; OLIGONUCLEOTIDE;

ARTICLE; CONJUGATION; MASS SPECTROMETRY;

BASE PAIR MISMATCH; CISPLATIN; DNA; DNA ADDUCTS; INTERCALATING AGENTS; OLIGONUCLEOTIDES; ORGANOMETALLIC COMPOUNDS;

EID: 8844234926     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047235l     Document Type: Article

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21. Complexes were utilized as a mixture of configurational isomers.
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23. Adduct formation levels off after 10 h under these conditions.
24. Since the observed photocleavage could have been due to residual unreacted conjugate, we also separated the incubated duplex from free conjugate via molecular sieves prior to irradiation. The irradiation patterns of the purified samples (Figure 2, lanes 6) are very similar to unfiltered mixtures (lanes 5), suggesting that the intercalator is still able to interact with the mismatched site within DNA adducts. In addition, since the coordination adducts with the oligonucleotide targets may have a different migration than the related Maxam Gilbert fragments, the irradiated incubated samples were treated with cyanide in order to reverse the adducts to yield unmetalated oligonucleotide fragments. Product analysis does not reveal new species, confirming that the intercalator mainly resides close to the mismatch, even in the coordination adducts (see Supporting Information).
25. Coordination of 1 but not 2 to the DNA duplex is also evident in Figure 2.
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29. 2 using 5 μM DNA, 5 μM Pt.
30. Varying the reaction conditions (nature and concentration of the buffer, temperature) affects the yield of adduct formed but does not affect the selectivity significantly.
31. Absolute yield of ad2 is noteworthy. Whereas reaction with CC3 results in ∼5.2% ad1 and ∼2% ad2, with CC9, adducts ad2 are more abundant (∼7%) than adducts ad1 (∼3.6%).
32. 5′ labeling of the complementary strand (not containing the GG) confirms that the interstrand adducts are more abundant than their faster moving intrastrand counterparts (by a factor of ∼1.4 in this G-rich complement).