Acridine-psoralen amines and their interaction with deoxyribonucleic acid
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Acridine-psoralen amines and their interaction with deoxyribonucleic acid. / Hansen, J B; Koch, T.; Buchardt, O; Nielsen, Peter E.; Wirth, M; Nordén, B.
In: Biochemistry, Vol. 22, No. 21, 11.10.1983, p. 4878-86.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Acridine-psoralen amines and their interaction with deoxyribonucleic acid
AU - Hansen, J B
AU - Koch, T.
AU - Buchardt, O
AU - Nielsen, Peter E.
AU - Wirth, M
AU - Nordén, B
PY - 1983/10/11
Y1 - 1983/10/11
N2 - A series of novel compounds in which a 9-acridinyl nucleus is linked to a psoralen nucleus in the 5- or 8-position via polyamines was prepared and examined. Their reversible binding to DNA and their irreversible binding to DNA and DNA cross-linking upon irradiation with UV-A light were examined. It was found that they were all less efficiently photoreactive than 8-methoxypsoralen (8-MOP), both in cross-linking and photobinding to DNA, whereas the ratio between their photobinding and cross-linking was 40-400 times that of 8-MOP. Compounds in which the linker was attached to the 5-position in psoralen showed smaller cross-linking and photobinding efficiencies and larger ratios between photobinding and cross-linking than those of psoralens attached in the 8-position. This strongly indicates that the 9-substituents of the acridines are oriented toward the minor groove. Flow linear dichroism studies showed that the compounds were DNA intercalating with the acridine moiety, whereas the psoralen moiety in no case was clearly intercalating. This conclusion was further supported by viscometry which also strongly indicated monointercalation.
AB - A series of novel compounds in which a 9-acridinyl nucleus is linked to a psoralen nucleus in the 5- or 8-position via polyamines was prepared and examined. Their reversible binding to DNA and their irreversible binding to DNA and DNA cross-linking upon irradiation with UV-A light were examined. It was found that they were all less efficiently photoreactive than 8-methoxypsoralen (8-MOP), both in cross-linking and photobinding to DNA, whereas the ratio between their photobinding and cross-linking was 40-400 times that of 8-MOP. Compounds in which the linker was attached to the 5-position in psoralen showed smaller cross-linking and photobinding efficiencies and larger ratios between photobinding and cross-linking than those of psoralens attached in the 8-position. This strongly indicates that the 9-substituents of the acridines are oriented toward the minor groove. Flow linear dichroism studies showed that the compounds were DNA intercalating with the acridine moiety, whereas the psoralen moiety in no case was clearly intercalating. This conclusion was further supported by viscometry which also strongly indicated monointercalation.
KW - Acridines/chemical synthesis
KW - Amines
KW - Animals
KW - Cattle
KW - Chemical Phenomena
KW - Chemistry
KW - DNA
KW - Furocoumarins/chemical synthesis
KW - Indicators and Reagents
KW - Magnetic Resonance Spectroscopy
KW - Mass Spectrometry
KW - Spectrophotometry, Infrared
KW - Spectrophotometry, Ultraviolet
KW - Structure-Activity Relationship
KW - Thymus Gland
U2 - 10.1021/bi00290a003
DO - 10.1021/bi00290a003
M3 - Journal article
C2 - 6639934
VL - 22
SP - 4878
EP - 4886
JO - Biochemistry
JF - Biochemistry
SN - 0006-2960
IS - 21
ER -
ID: 203631925