DNA-binding properties and photocleavage activity of cationic water-soluble chlorophyll derivatives.
Three cationic water-soluble chlorin e(6) derivatives, that is, 6a-,gammab-,7c-tris(2-trimethylammonioethyl)chlorin e(6) (1), 6a-,gammab-,7c-tris(3-methylpyridiniummethyl)chlorin e(6) (2), and 6a-,gammab-, 7c-tris(2-trimethylammonioethyl)-2-(3-trimethylammonioprop-1-enyl)chlorin e(6) (3), have been designed and synthesized to allow the study of their DNA-binding and -photocleavage activities. The DNA-unwinding assay, measurements of melting temperatures of double-stranded DNA, and the induced CD and visible absorption spectra have revealed that 1 and 3 are intercalated into the base pairs of the double-helical DNA, while 2 is bound to outside the minor groove of the double-helical DNA. The cationic water-soluble chlorin e(6) derivatives effectively cleave the double-helical DNA under photoirradiation and the DNA-photocleavage activity increases in the order 3>1>2. The DNA-binding and -photocleavage characteristics of the three cationic water-soluble chlorin e(6) derivatives are influenced by aspects of their molecular structure, such as the kind, number, and position of the cationic substituents.
Taima
Hidetoshi
H
Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Okubo
Akihiro
A
Yoshioka
Naoki
N
Inoue
Hidenari
H
D002412:Cations; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002734:Chlorophyll / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D002735:Chlorophyllides; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D010777:Photochemistry; D011166:Porphyrins / Q000737:chemistry*; D011838:Radiation-Sensitizing Agents / Q000737:chemistry*; D012995:Solubility; D014867:Water / Q000737:chemistry
D002412:Cations; D002735:Chlorophyllides; D011166:Porphyrins; D011838:Radiation-Sensitizing Agents; D014867:Water; D002734:Chlorophyll; C062985:phytochlorin; D004247:DNA