ChemInform Abstract: DIETHYLAMINOALKYLOXYCOUMARIN AND ‐FUROCOUMARIN DERIVATIVES

Antonello, C; Magno, Sebastiano Marciani; Gia, Ornella; Carlassare, F.; Baccichetti, F.; Bordin, F.

doi:10.1002/chin.197924229

Cited by 5 publications

(8 citation statements)

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“…8‐(3‐Bromopropyloxy)‐psoralen ( 3 ) was obtained by the reaction of 8‐hydroxypsoralen with 1,3‐dibromopropane (18). To a stirred solution of 2 (3.7 g, 18.3 mmol) in acetone (260 mL) were added K 2 CO 3 (7.9 g, 52.9 mmol) and 1,3‐dibromopropane (10.6 g, 52.9 mmol).…”

Section: Methodsmentioning

confidence: 99%

On the Photobiological Properties of Chimeras Combining Quaternary Ammonium Derivatives of Retinoic Amides and Psoralen. A Study with Cultured Human Keratinocytes¶†

Lartillot¹,

Risler²,

Andriamialisoa³

et al. 2007

Photochemistry and Photobiology

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The effectiveness of the combination of retinoids with 8‐methoxypsoralen (8‐MOP) and ultraviolet‐A (UV‐A) light in the treatment of some cutaneous proliferative diseases has motivated the synthesis of new “chimera‐type” molecules built from psoralen derivatives and retinoic amides and related molecules. The chimeras result from the combination of 8‐(3‐bromopropyloxy)‐psoralen with amides prepared by reacting 4‐amino‐pyridine with 13E‐ and 13Z‐retinoic acids or a “retinoid‐like” derivative with an alkene chain of only three double bonds. The synthesis of chimeras built with the 8‐(3‐bromopropyloxy)‐psoralen and the amide of cinnamic acid or its 4‐methoxy derivative has also been carried out. In contrast to 8‐MOP, all the chimeras exhibit strong molar absorptivities in the range 20 000–40 000 M−1cm−1 in the 340–390 nm UV‐A region. The “retinoid‐like”– and retinoid–psoralen chimeras are characterized by a marked dark toxicity toward proliferating NCTC 2544 keratinocytes (with a lethal dose corresponding to 50% cell survival [LD50] of 1–5 μM) as compared with that of the cinnamic acid derivative–psoralen chimeras (LD50≥ 50 μM). This toxicity leads to alteration of the mitochondrial membrane potential. At nontoxic concentrations, the chimeras demonstrate effective psoralens + UV‐A–induced photocytotoxicity. They are moderate photosensitizers of membrane lipid peroxidation. Cell apoptosis is a major photocytotoxic process as suggested by the fluorescence‐activated cell‐sorting technique using annexin–fluorescein isothiocyanate and propidium iodide as apoptotic markers.

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Section: Methodsmentioning

confidence: 99%

On the Photobiological Properties of Chimeras Combining Quaternary Ammonium Derivatives of Retinoic Amides and Psoralen. A Study with Cultured Human Keratinocytes¶†

Lartillot¹,

Risler²,

Andriamialisoa³

et al. 2007

Photochemistry and Photobiology

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“…8‐Methoxypsoralen was demethylated with tribromoboron 8 and reacted with 1,3‐dibromopropane to give 8‐(3′‐bromopropanoxyl)psoralen following the procedure of Antonello et al 9 . This compound and 8‐MOP were nitrated with fuming nitric acid in acetic acid and reduced to amines by zinc and stannous chloride 10–11 .…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of 8‐hydroxypsoralen, 8 8‐(3′‐bromopropanoxy)psoralen, 9 8‐methoxy‐5‐nitropsoralen 11 and 5‐amino‐8‐methoxypsoralen have been described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

“…Solutions were then sterilized by filtration using Acrodisc syringe filters (0.2 μm, Gelman Sciences, Ann Arbor, MI) and stored at 4°C. Their concentrations were determined spectrophotometrically by using the following extinction coefficients: ethidium bromide, 12 ε 480 = 5860 M 1 cm 1 ; calf thymus DNA, ε 260 = 6600 M 1 cm 1 ; 11 , 9 ε 303 = 1.145 × 10 4 M 1 cm 1 ; 1 and 2 , ε 120 = 1.40 × 10 4 M 1 cm 1 . Binding constants were measured by a modification of the Hansen et al ethidium bromide fluorescence displacement assay 13 : A series of 2 mL solutions were made with constant concentrations of calf thymus DNA with varying concentrations of the compound in question.…”

Section: Methodsmentioning

confidence: 99%

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Exploratory Photochemistry of 5‐azido‐8‐alkoxy–substituted Psoralens Free and Bound to Dna

Chen

Michalak

Platz

1995

Photochem & Photobiology

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5-Azido-8-alkoxy psoralens were synthesized. Laser flash photolysis (LFP: XeF, 351 nm, 55 mJ, 17 ns) of the azides in acetonitrile or benzene solution produces the triplet nitrene and a small amount of ketenimine. Laser flash photolysis of the azides in methanol or aqueous solution cleanly produces the triplet nitrene. In aqueous solution containing highly polymerized calf thymus DNA, LFP produces a mixture of triplet nitrene and ketenimine corresponding to photolysis of free and bound psoralen, respectively. The two transients decay slowly but at different rates. Assignment of the transient spectra were secured by matrix EPR and UV-visible spectroscopy. The triplet nitrene lifetime is the same in buffer and in the presence and absence of calf thymus DNA. The results explain why psoralen azides are unable to efficiently nick plasmid DNA pBR322 upon UV activation.

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“…(1) followed by treatment with 1,3-dibromopropane (Antonello et al, 1979), 8-[[(3-diethylamino)propyl]oxy]psoralen (3a) by treatment of 2 with diethylamine (Antonello et al, 1979), and the acridines 6a-c and 61) by treatment of 9-chloroacridine or 2-methoxy-6,9-dichloroacridine with the relevant polyamines as previously described (Hansen et al, 1983). The psoralenacridine heterodimers were prepared as described for compounds 9a-2HCl and 9b*2HCl.…”

Section: Methodsmentioning

confidence: 99%

Acridine-psoralen amines and their interaction with deoxyribonucleic acid

Hansen¹,

Koch²,

Buchardt³

et al. 1983

Biochemistry

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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.

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ChemInform Abstract: DIETHYLAMINOALKYLOXYCOUMARIN AND ‐FUROCOUMARIN DERIVATIVES

Abstract: Durch Umsetzung der Phenole (Ia)‐(IVa) mit Dibromalkanen und nachfolgende Reaktion mit Diethylamin erhält man die Diethylaminoalkyloxy‐Verbindungen (Ic)‐(IVc).

Cited by 5 publications

References 0 publications

On the Photobiological Properties of Chimeras Combining Quaternary Ammonium Derivatives of Retinoic Amides and Psoralen. A Study with Cultured Human Keratinocytes¶†

On the Photobiological Properties of Chimeras Combining Quaternary Ammonium Derivatives of Retinoic Amides and Psoralen. A Study with Cultured Human Keratinocytes¶†

Exploratory Photochemistry of 5‐azido‐8‐alkoxy–substituted Psoralens Free and Bound to Dna

Acridine-psoralen amines and their interaction with deoxyribonucleic acid

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