Disease relevance of Terthiophene

• Characterization of cutaneous phototoxicity induced by topical alpha-terthienyl and ultraviolet A radiation [1].
• After irradiation with near UV light, alpha-terthienyl and most of its analogues had significant toxicity, with minimum inhibitory concentrations in the range of 0.02-40 microM [2].
• Intracellular target for alpha-terthienyl photosensitization: involvement of lysosomal membrane damage [3].
• A number of carboxylic acid derivatives of the photoactive terthiophene, alpha-terthienyl, were found to possess impressive UVA-dependent activity against the human immunodeficiency virus, HIV-1; but only when assayed in the absence of serum, indicating that the latter contained interfering components [4].
• Photodynamic hemolysis caused by alpha-terthienyl [5].

High impact information on Terthiophene

• This system was studied by following the inhibition of glucose-6-phosphate dehydrogenase by photoactivated alpha-terthienyl and protection of the enzyme activity in the absence of oxygen and by various additions [6].
• We analyze the electronic and molecular structures for the ground and excited electronic states of aromatic terthiophene (3T), the quinodimethane 3',4'-dibutyl-5,5' '-bis(dicyanomethylene)-5,5' '-dihydro-2,2':5',2' '-terthiophene (3Q), and isologues with the middle ring S-oxidized (3TO2, 3QO2) [7].
• Energy transfer was observed between the metal surface plasmon absorption and fluorescence of the terthiophene dendrons [8].
• The rate constant is insensitive to the mode of attachment to the surface but displays a significant viscosity dependence, change with spacer composition (alkane versus terthiophene), and nature of the solvent (H(2)O versus D(2)O) [9].
• A theoretical study on the low-lying excited states of 2,2':5',2''-terthiophene and 2,2':5',2'':5'',2'''-quaterthiophene [10].

Chemical compound and disease context of Terthiophene

• Various synthetic analogues of the naturally occurring terthiophene, alpha-terthienyl (alpha T), were evaluated for anti-human immunodeficiency virus (HIV) activity [11].
• The photoactivated antiviral and cytotoxic activities of the naturally occurring thiophene, alpha-terthienyl (1), and 15 synthetic analogues were evaluated against murine cytomegalovirus and Sindbis virus, and murine mastocytoma cells [2].
• Coexposure to 400 muw/cm2 for 15 min increased the toxicity of psoralen, alpha-terthienyl, anthracene, acridine, fluoranthene, TNT, Cu2-, As3-, Ni2, and Cd2+ [12].

Biological context of Terthiophene

• When the Asteraceae-derived photooxidant alpha-terthienyl was co-administered, lipid peroxidation and larval mortality were significantly enhanced in the treated groups of insects with lowered in vivo glutathione levels [13].
• The carboxaldehyde and hydroxymethyl derivatives of alpha-terthiophene were potent PKC inhibitors (IC50 = 10(-7) M) [14].
• Examination of naturally occurring polyacetylenes and alpha-terthienyl for their ability to induce cytogenetic damage [15].
• alpha-Terthienyl and 5 polyacetylenes were examined for chromosome damaging activity using Syrian hamster cells [15].
• Pharmacokinetics, metabolism and toxicity of the plant-derived photoxin alpha-terthienyl [16].

Anatomical context of Terthiophene

• Photoinactivation of human erythrocyte enzymes by alpha-terthienyl and phenylheptatriyne, naturally occurring compounds in the Asteraceae [17].
• We report a new aspect of rapid (<30 s) light-induced cell membrane damage photosensitized by 5,5"-bis(aminomethyl)-2,2':5',2"-terthiophene dihydrochloride (BAT), which is a water-soluble alpha-terthienyl analogue, using a high-power laser (light intensity 1.6 W cm(-2)) [18].

Associations of Terthiophene with other chemical compounds

• Picosecond time-resolved fluorescence spectroscopy reveals that unsubstituted terthiophene has the shortest emission lifetime of 140 ps in acetonitrile [19].
• Suppression of carotenoid formation by inactivation of the katF gene lowered, but did not abolish, the protection offered by carotenoids against inactivation by alpha-terthienyl plus near-ultraviolet light (320-400 nm) [20].
• In liposomes with highly ordered lipid where the fatty acid side chains are saturated, alpha-terthienyl had no effect on glucose permeability [21].
• Triplet states of poly(phenylene ethynylene), (3)PPE(*), not easily formed by direct photoexcitation, were produced by pulse radiolysis in toluene, along with triplet states of T(3)PPE having terthiophene end-caps [22].
• Enhanced permeability to glucose in these liposomes due to the action of alpha-terthienyl and phenylheptatriyne involved lipid peroxidation, but neither of the two assays used to monitor lipid peroxidation (malondialdehyde and peroxide formation) was directly correlated with the increase in liposome permeability [21].

Gene context of Terthiophene

• Hexamer 1(6T) was synthesized by oxidative coupling of terthiophene 12, tris-annelated with BCO units, in 81% yield [23].
• The triplet energy of alpha-terthienyl has been determined by heavy atom-induced optical absorption: the value of 39.7 +/- 1.5 kcal/mol is consistent with earlier energy transfer work [24].

Analytical, diagnostic and therapeutic context of Terthiophene

• Raman spectroscopy of short-lived terthiophene radical cations generated by photochemical and chemical oxidation [25].
• We provide evidence for the generation of a free radical viz., superoxide anion radical, by alpha-terthienyl employing spin-trapping techniques, probably due to the extension of the latter reaction [26].

References