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Oxidative Repair of a Thymine Dimer in DNA from a Distance by a Covalently Linked Organic Intercalator

Vicic, David A. and Odom, Duncan T. and Núñez, Megan E. and Gianolio, Diego A. and McLaughlin, Larry W. and Barton, Jacqueline K. (2000) Oxidative Repair of a Thymine Dimer in DNA from a Distance by a Covalently Linked Organic Intercalator. Journal of the American Chemical Society, 122 (36). pp. 8603-8611. ISSN 0002-7863. doi:10.1021/ja000280i.

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A thymine cyclobutane dimer, site-specifically incorporated in a DNA duplex, is shown to be repaired upon photoexcitation (at 380 nm) of a naphthalene diimide intercalator (NDI), either bound noncovalently to the duplex or covalently appended to the C4 amine of a methylated cytosine base well separated from the thymine dimer. The repair of the thymine dimer is triggered by photooxidation either directly or by DNA-mediated charge transport over a distance of ∼22 Å, the separation between NDI and the cyclobutane ring. Photooxidative repair with covalently and noncovalently bound NDI is demonstrated using HPLC under denaturing conditions, where the loss of the thymine dimer-containing strand and the formation of the repaired strand are monitored directly, as well as using a novel gel electrophoretic assay. In this assay, two strands of oligonucleotides containing 5‘- and 3‘-terminal thymidines are first ligated photochemically to yield thymine dimers, and repair is then assayed by monitoring the reversal of the photoligation by intercalators bound either noncovalently or at a distance. Although both NDI and a rhodium intercalator were seen to reverse the photoligation, several anthraquinones and ethidium were unable to promote repair upon irradiation at 350 nm. This photoligation reversal assay provides a rapid screen for thymine dimer repair. The oxidative repair of thymine dimers in a DNA duplex from a distance appears now to be a general phenomenon and requires consideration in developing mechanisms for DNA-mediated charge transport.

Item Type:Article
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Barton, Jacqueline K.0000-0001-9883-1600
Additional Information:© 2000 American Chemical Society. Received 25 January 2000. Published online 23 August 2000. Published in print 1 September 2000. We are grateful to the National Institutes of Health (GM37065 to L.W.M. and GM49216 to J.K.B.) for their financial support of this work. D.A.V. acknowledges the American Cancer Society for a postdoctoral fellowship (#PF-99-332-01-CNE). M.E.N. acknowledges the Howard Hughes Medical Institute predoctoral fellowship program for funding, and D.T.O. acknowledges the Parsons Foundation.
Funding AgencyGrant Number
American Cancer SocietyPF-99-332-01-CNE
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
Ralph M. Parsons FoundationUNSPECIFIED
Issue or Number:36
Record Number:CaltechAUTHORS:20170404-094144114
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Official Citation:Oxidative Repair of a Thymine Dimer in DNA from a Distance by a Covalently Linked Organic Intercalator David A. Vicic, Duncan T. Odom, Megan E. Núñez, Diego A. Gianolio, Larry W. McLaughlin, and Jacqueline K. Barton Journal of the American Chemical Society 2000 122 (36), 8603-8611 DOI: 10.1021/ja000280i
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75675
Deposited By: Ruth Sustaita
Deposited On:04 Apr 2017 19:12
Last Modified:15 Nov 2021 16:35

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