Interaction of anthracene and its oxidative derivatives with human serum albumin.

Abstract

Binding affinities of ten polycyclic aromatic hydrocarbons to albumin were determined: anthracene, its eight oxy-derivatives: anthraquinone, 9-anthracenemethanol, 9-anthraldehyde, 9-anthracenecarboxylic acid, 1,4-dihydroxyanthraquinone, 1,5-dihydroxyanthraquinone, 1,8-dihydroxyanthraquinone, 2,6-dihydroxyanthraquinone and benzo[a]pyrene. The quenching of albumin fluorescence was used to measure the PAH - protein interaction. The theoretical curve of calculated fluorescence was fitted to experimental data after necessary corrections regarding PAHs fluorescence and inner filter effect. From the numerical fitting the final association constants were calculated. Anthracene and anthraquinone failed to quench the albumin fluorescence. 9-anthracenecarboxylic acid showed the highest, while 9-anthracenemethanol the weakest albumin binding affinity. The affinity constants determined for 9-anthraldehyde and benzo[a]pyrene were of the same magnitude and indicated low-affinity binding to albumin. The constants obtained for the four dihydroxyanthraquinones were higher, but dissimilar, which suggests that the position of the functional group in anthracene molecule influences the binding constant. Moreover, this study suggests that the type of substituent plays a significant role in PAH-albumin complex formation. The carboxylic group increases the binding affinity of the anthracene molecule the most rather than the presence of both carbonyl and hydroxyl groups. The lowest affinity constants were obtained for aldehyde, methyl and carbonyl substituents.

Photoresponsive PEG-Anthracene Grafted Hyaluronan as a Controlled-Delivery Biomaterial

“…With photo-cross-linking, it also releases over a relatively lengthy time extending past 2.5 months. Interestingly, past studies have shown some interaction exists between anthracene derivatives and human serum albumin . Therefore, it is possible that these interactions contribute to the lengthy release time of BSA from the photogels despite its low loading and attraction.…”

“…Interestingly, past studies have shown some interaction exists between anthracene derivatives and human serum albumin. 35 Therefore, it is possible that these interactions contribute to the lengthy release time of BSA from the photogels despite its low loading and attraction. Lysozyme, which is slightly positive at pH 7.4 due to its high pI, should show a small attraction to the HA photogels.…”

Micelles Embedded in Multiphasic Protein Hydrogel Enable Efficient and Air-Tolerant Triplet Fusion Upconversion with Heavy-Atom and Spin–Orbit Charge-Transfer Sensitizers

“…Furthermore, TTA-UC was not observed from deaerated BSA/upconverter complexes. This is because serum albumin binds only one anthracene or perylene-based molecule, , which is not enough to appease the TTA-UC mechanism. Conversely, TTA-UC was observed from a deaerated solution of SDS/upconverter micelles.…”

Metabolism and removal of anthracene and lead by a B. subtilis-produced biosurfactant

“…The Environmental Protection Agency has introduced these compounds as dangerous pollutants because of their high stability and toxicity [ 2 ]. Anthrancene is an aromatic hydrocarbon, with low solubility in the water and high accumulation affinity in organism tissues [ 3 , 4 ]. Allowable limit of anthrancene identified by Canadian Council of Ministers of the Environment [ 5 ] for sediment is 46.9 μg/kg.…”