A [2+2] photo-adduct of 8-methoxypsoralen and thymine: x-ray crystal structure. A model for the reaction of psoralens with DNA in the phototherapy of psoriasis

Edward J Land; Francis A P Rushton; Roy L Beddoes; J Malcolm Bruce; Robert J Cernik; Shiona C Dawson; Owen S Mills

doi:10.1039/c39820000022

A [2+2] photo-adduct of 8-methoxypsoralen and thymine: x-ray crystal structure. A model for the reaction of psoralens with DNA in the phototherapy of psoriasis

Edward J Land, Francis A P Rushton, Roy L Beddoes, J Malcolm Bruce, Robert J Cernik, Shiona C Dawson, Owen S Mills

Research output: Contribution to journal › Article › peer-review

Abstract

UV irradn. of a mixt. of 8-methoxypsoralen and thymine in ice-MeOH contg. Ph2CO as photosensitizer for 20 min gave ∼3% [2+2]-adduct I. The structure of I was detd. by x-ray crystallog.; the bonding of the 4'- and 5'-positions of the methoxypsoralen to the 5- and 6-positions of the thymine, resp., was cis. [on SciFinder(R)]

Original language	English
Pages (from-to)	22-3
Number of pages	18
Journal	J. Chem. Soc., Chem. Commun.
Issue number	1
DOIs	https://doi.org/10.1039/c39820000022
Publication status	Published - 1982

Keywords

Crystal structure
Molecular structure (of methoxypsoralen-thymine cycloadduct)
Psoriasis (psoralen phototherapy of, model reaction study of)
photochem cycloaddn methoxypsoralen thymine
crystal structure methoxypsoralen thymine cycloadduct
mol structure methoxypsoralen thymine cycloadduct
psoralen methoxy thymine cycloadduct structure
psoriasis treatment psoralen DNA model

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title = "A [2+2] photo-adduct of 8-methoxypsoralen and thymine: x-ray crystal structure. A model for the reaction of psoralens with DNA in the phototherapy of psoriasis",

abstract = "UV irradn. of a mixt. of 8-methoxypsoralen and thymine in ice-MeOH contg. Ph2CO as photosensitizer for 20 min gave ∼3% [2+2]-adduct I. The structure of I was detd. by x-ray crystallog.; the bonding of the 4'- and 5'-positions of the methoxypsoralen to the 5- and 6-positions of the thymine, resp., was cis. [on SciFinder(R)]",

keywords = "Crystal structure, Molecular structure (of methoxypsoralen-thymine cycloadduct), Psoriasis (psoralen phototherapy of, model reaction study of), photochem cycloaddn methoxypsoralen thymine, crystal structure methoxypsoralen thymine cycloadduct, mol structure methoxypsoralen thymine cycloadduct, psoralen methoxy thymine cycloadduct structure, psoriasis treatment psoralen DNA model",

author = "Land, {Edward J} and Rushton, {Francis A P} and Beddoes, {Roy L} and Bruce, {J Malcolm} and Cernik, {Robert J} and Dawson, {Shiona C} and Mills, {Owen S}",

note = "CAN 96:217790 Heterocyclic Compounds (More Than One Hetero Atom) 65-71-4 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reaction of, with methoxypsoralen, photochem.); 298-81-7 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reaction of, with thymine, photochem.); 81803-28-3P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. and crystal and mol. structure of)",

year = "1982",

doi = "10.1039/c39820000022",

language = "English",

pages = "22--3",

journal = "J. Chem. Soc., Chem. Commun.",

issn = "0022-4936",

publisher = "Chemical Society",

number = "1",

}

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T1 - A [2+2] photo-adduct of 8-methoxypsoralen and thymine: x-ray crystal structure. A model for the reaction of psoralens with DNA in the phototherapy of psoriasis

AU - Land, Edward J

AU - Rushton, Francis A P

AU - Beddoes, Roy L

AU - Bruce, J Malcolm

AU - Cernik, Robert J

AU - Dawson, Shiona C

AU - Mills, Owen S

N1 - CAN 96:217790 Heterocyclic Compounds (More Than One Hetero Atom) 65-71-4 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reaction of, with methoxypsoralen, photochem.); 298-81-7 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reaction of, with thymine, photochem.); 81803-28-3P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. and crystal and mol. structure of)

PY - 1982

Y1 - 1982

N2 - UV irradn. of a mixt. of 8-methoxypsoralen and thymine in ice-MeOH contg. Ph2CO as photosensitizer for 20 min gave ∼3% [2+2]-adduct I. The structure of I was detd. by x-ray crystallog.; the bonding of the 4'- and 5'-positions of the methoxypsoralen to the 5- and 6-positions of the thymine, resp., was cis. [on SciFinder(R)]

AB - UV irradn. of a mixt. of 8-methoxypsoralen and thymine in ice-MeOH contg. Ph2CO as photosensitizer for 20 min gave ∼3% [2+2]-adduct I. The structure of I was detd. by x-ray crystallog.; the bonding of the 4'- and 5'-positions of the methoxypsoralen to the 5- and 6-positions of the thymine, resp., was cis. [on SciFinder(R)]

KW - Crystal structure

KW - Molecular structure (of methoxypsoralen-thymine cycloadduct)

KW - Psoriasis (psoralen phototherapy of, model reaction study of)

KW - photochem cycloaddn methoxypsoralen thymine

KW - crystal structure methoxypsoralen thymine cycloadduct

KW - mol structure methoxypsoralen thymine cycloadduct

KW - psoralen methoxy thymine cycloadduct structure

KW - psoriasis treatment psoralen DNA model

U2 - 10.1039/c39820000022

DO - 10.1039/c39820000022

M3 - Article

SN - 0022-4936

SP - 22

EP - 23

JO - J. Chem. Soc., Chem. Commun.

JF - J. Chem. Soc., Chem. Commun.

IS - 1

ER -

A [2+2] photo-adduct of 8-methoxypsoralen and thymine: x-ray crystal structure. A model for the reaction of psoralens with DNA in the phototherapy of psoriasis

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Keywords

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