Isolation and characterization of pyrimidine-psoralen-pyrimidine photodiadducts from DNA

Kanne, David B.; Straub, Kenneth; Hearst, John E.; Rapoport, Henry

doi:10.1021/ja00388a046

Cited by 195 publications

(135 citation statements)

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“…The major bis adduct formed when 8-MOP or trioxsalen reacts with double-stranded DNA has been isolated, and its structure has been characterized by NMR (1,22). Two thymines are involved; they form cyclobutane rings with the 3,4-double bond on the pyrone ring and the 4',5'-double bond on the furane ring.…”

Section: Resultsmentioning

confidence: 99%

Sequence-specific photo-induced cross-linking of the two strands of double-helical DNA by a psoralen covalently linked to a triple helix-forming oligonucleotide.

Takasugi

Guendouz

Chassignol

et al. 1991

Proc. Natl. Acad. Sci. U.S.A.

232

165

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On the basis of the structure of DNA-psoralen bis adducts (formed by psoralen with two thymines on opposite strands), a psoralen-oligonucleotide conjugate was designed to photoinduce a cross-link between the two DNA strands at a specific sequence. Psoralen was attached via its C-5 position to a 5'-thiophosphate group of an 11-mer homopyrimidine oligonucleotide. The 11-mer binds to an 11-base-pair homopurinehomopyrimidine sequence of a DNA fragment, where it forms a triple helix. Upon near-UV-irradiation, the two strands of DNA are crosslinked at the TpA step present at the triplex-duplex junction. The reaction is specific for the homopurine'homopyrimidine DNA sequence and requires both oligonucleotide recognition of the DNA major groove and intercalation of psoralen at the triplex-duplex junction. The yield of the photoinduced cross-linking reaction is quite high (>80%). Such psoralen-oligonucleotide conjugates are probes of sequencespecific triple-helix formation and could be used to selectively control gene expression or to induce site-directed mutations.

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Section: Resultsmentioning

confidence: 99%

Sequence-specific photo-induced cross-linking of the two strands of double-helical DNA by a psoralen covalently linked to a triple helix-forming oligonucleotide.

Takasugi

Guendouz

Chassignol

et al. 1991

Proc. Natl. Acad. Sci. U.S.A.

232

165

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“…Another evidence for the formation of an interstrand cross-link is shown on Figure 5, which exhibits large upfield shifts for protons H5' (4 (29)(30)(31)(32). Cross peaks H6(T1)-H3(pso), H4(pso)-H3(pso), H5'(pso)-H6(T2) and H5'(pso)-H4'(pso) are also observed on the DQF-COSY spectrum, showing that cycloaddition have taken place between the 5-6 double bond ofT1 and the 3-4 (pyrone) double bond of psoralen, and between the 5-6 double bond of T2 and the 4'-5' (furan) double bond ofpsoralen.…”

Section: Location Of the Psoralen Derivativementioning

confidence: 89%

“…NMR analysis of diadducts formed by several psoralen molecules with DNA has revealed that the cross-link between the two strands of DNA involves two thymines, one on each strand of DNA at 5'TpA3' sequences (27,(29)(30)(31) …”

Section: Location Of the Psoralen Derivativementioning

confidence: 99%

Solution structure of oligonucleotides covalently linked to a psoralen derivative

et al. 1995

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maps, revealed that the mini double helix adopts a B-form conformation and that the deoxyriboses preferentially adopt a C2'-endo conformation. The nOe connectivities observed between the protons of the bases or the sugars In each duplex, and the protons of the psoralen and the hexamethylene chain, led us to propose a model involving an equilibrium between two conformations due to different locations of the psoralen. Upon UV-irradiation, the psoralen moiety crosslinked the two DNA strands at the level of 5'TpA3' sequences. NMR studies of the single major photocross-linked duplex pso-m6-d(TAAGCCG) and d(CGG-CTTA) were performed. The stereochemistry of the diadduct is indeed cis-syn at both cyclobutane rings. In addition, the effects of this diadduct on the helical structure are analyzed In detail.

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“…Psoralens may intercalate with DNA in the dark [29] and may, upon irradiation (320-400 nm), form photocycloaddition products, most frequently with thymidine in the cis-syn orientation [30]. Such reactions involve the 2'-3' and 3-4 double bonds.…”

Section: Discussionmentioning

confidence: 99%

Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. Microsomal conversion of (+)marmesin into psoralen

Wendorff

Matern

1986

Eur J Biochem

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Microsomal fractions isolated from parsley cell suspension cultures, which had been challenged with an elicitor from either Alternaria carthami or PI1 ~~tlrophthora megasperma f. sp. glycinea, catalyzed the formation of psoralen from synthetic [3-'4C](+)marmesin. Whereas psoralen was the only product formed in incubations with Alternaria-induced microsomes, another unidentified product was isolated from incubations with Phythophthorainduced microsomes. The latter product is neither a precursor nor a product of psoralen. In contrast, microsomes isolated from non-induced parsley cells lacked both of these catalytic activities. The formation of psoralen depends on NADPH as a cofactor and molecular oxygen. Blue-light-reversible CO inhibition and inhibition by various synthetic chemicals known to bind to cytochromes P450 indicated that the reaction is catalyzed by an elicitorinducible cytochrome P,,,-dependent psoralen synthase. Fractionation of microsomal preparations by centrifugation revealed that psoralen synthase is associated with the endoplasmic reticulum. Our results suggest that the endoplasmic reticulum of cultured parsley cells is the primary target in the previously reported differential induction by elicitors from these two non-pathogenic strains of fungi.Continuously dark-cultured parsley cells accumulate and excrete various linear furanocoumarin and a pyronocoumarin phytoalexins in response to elicitor challenge, as was shown previously using crude cell-wall fractions from two nonpathogenic fungi (Alternaria carthami and Phythophthora megasperma f. sp. glycinea) [I, 21. The relative composition of the coumarins induced varied significantly in response to the two elicitors. Furthermore, the increase in fresh weight of A. carthami (Ac) elicitor-induced parsley cells was comparable to that of untreated controls [3], suggesting that the primary metabolism of the cells was not severely altered, whereas comparable amounts of P. megasperma (Pmg) elicitor inhibited the growth of the cells. Since massive synthesis of the coumarins was observed within a few hours of addition of either one of the elicitors, parsley cells appeared to represent Correspondence to U. Matern, Lehrstuhl fiir Biochemie der

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Isolation and characterization of pyrimidine-psoralen-pyrimidine photodiadducts from DNA

Cited by 195 publications

References 0 publications

Sequence-specific photo-induced cross-linking of the two strands of double-helical DNA by a psoralen covalently linked to a triple helix-forming oligonucleotide.

Sequence-specific photo-induced cross-linking of the two strands of double-helical DNA by a psoralen covalently linked to a triple helix-forming oligonucleotide.

Solution structure of oligonucleotides covalently linked to a psoralen derivative

Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. Microsomal conversion of (+)marmesin into psoralen

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