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Acridine-psoralen amines and their interaction with deoxyribonucleic acid

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Standard

Acridine-psoralen amines and their interaction with deoxyribonucleic acid. / Hansen, J B; Koch, T.; Buchardt, O; Nielsen, Peter E.; Wirth, M; Nordén, B.

I: Biochemistry, Bind 22, Nr. 21, 11.10.1983, s. 4878-86.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Harvard

Hansen, JB, Koch, T, Buchardt, O, Nielsen, PE, Wirth, M & Nordén, B 1983, 'Acridine-psoralen amines and their interaction with deoxyribonucleic acid', Biochemistry, bind 22, nr. 21, s. 4878-86. https://doi.org/10.1021/bi00290a003

APA

Hansen, J. B., Koch, T., Buchardt, O., Nielsen, P. E., Wirth, M., & Nordén, B. (1983). Acridine-psoralen amines and their interaction with deoxyribonucleic acid. Biochemistry, 22(21), 4878-86. https://doi.org/10.1021/bi00290a003

Vancouver

Hansen JB, Koch T, Buchardt O, Nielsen PE, Wirth M, Nordén B. Acridine-psoralen amines and their interaction with deoxyribonucleic acid. Biochemistry. 1983 okt 11;22(21):4878-86. https://doi.org/10.1021/bi00290a003

Author

Hansen, J B ; Koch, T. ; Buchardt, O ; Nielsen, Peter E. ; Wirth, M ; Nordén, B. / Acridine-psoralen amines and their interaction with deoxyribonucleic acid. I: Biochemistry. 1983 ; Bind 22, Nr. 21. s. 4878-86.

Bibtex

@article{176f68c6836849d7a74add9c6fc69138,
title = "Acridine-psoralen amines and their interaction with deoxyribonucleic acid",
abstract = "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.",
keywords = "Acridines/chemical synthesis, Amines, Animals, Cattle, Chemical Phenomena, Chemistry, DNA, Furocoumarins/chemical synthesis, Indicators and Reagents, Magnetic Resonance Spectroscopy, Mass Spectrometry, Spectrophotometry, Infrared, Spectrophotometry, Ultraviolet, Structure-Activity Relationship, Thymus Gland",
author = "Hansen, {J B} and T. Koch and O Buchardt and Nielsen, {Peter E.} and M Wirth and B Nord{\'e}n",
year = "1983",
month = oct,
day = "11",
doi = "10.1021/bi00290a003",
language = "English",
volume = "22",
pages = "4878--86",
journal = "Biochemistry",
issn = "0006-2960",
publisher = "American Chemical Society",
number = "21",

}

RIS

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