The effect of light wavelength on in vitro bilirubin photodegradation and photoisomer production

Vreman, Hendrik J.; Kourula, Stephanie; Jašprová, Jana; Ludvíková, Lucie; Klán, Petr; Muchová, Lucie; Vı́tek, Libor; Cline, Benjamin K.; Wong, Ronald J.; Stevenson, David K.

doi:10.1038/s41390-019-0310-2

Cited by 24 publications

(16 citation statements)

References 41 publications

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“…In fact, bilirubin behaves as a bichromophore because of its molecular structure composed by two asymmetrical dipyrroles covalently linked by a methylene group [345]. This feature is responsible for exciton energy transfer events inside the chromophore, in turn affected by the molecule concentration, excitation wavelength and microenvironment, which can remarkably influence bilirubin absorption, fluorescence and quantum yield [346][347][348]. As a consequence, the changes occurring in bilirubin fluorescence depending on its biological medium can be exploited as a marker of liver functionality in the maintenance of systemic metabolism [349].…”

Section: Normal and Altered Cell And Tissuesmentioning

confidence: 99%

Light and Autofluorescence, Multitasking Features in Living Organisms

Croce

2021

Photochem

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Organisms belonging to all life kingdoms may have the natural capacity to fluoresce. Autofluorescence events depend on the presence of natural biomolecules, namely endogenous fluorophores, with suitable chemical properties in terms of conjugated double bonds, aromatic or more complex structures with oxidized and crosslinked bonds, ensuring an energy status able to permit electronic transitions matching with the energy of light in the UV-visible-near-IR spectral range. Emission of light from biological substrates has been reported since a long time, inspiring unceasing and countless studies. Early notes on autofluorescence of vegetables have been soon followed by attention to animals. Investigations on full living organisms from the wild environment have been driven prevalently by ecological and taxonomical purposes, while studies on cells, tissues and organs have been mainly promoted by diagnostic aims. Interest in autofluorescence is also growing as a sensing biomarker in food production and in more various industrial processes. The associated technological advances have supported investigations ranging from the pure photochemical characterization of specific endogenous fluorophores to their possible functional meanings and biological relevance, making fluorescence a valuable intrinsic biomarker for industrial and diagnostic applications, in a sort of real time, in situ biochemical analysis. This review aims to provide a wide-ranging report on the most investigated natural fluorescing biomolecules, from microorganisms to plants and animals of different taxonomic degrees, with their biological, environmental or biomedical issues relevant for the human health. Hence, some notes in the different sections dealing with different biological subject are also interlaced with human related issues. Light based events in biological subjects have inspired an almost countless literature, making it almost impossible to recall here all associated published works, forcing to apologize for the overlooked reports. This Review is thus proposed as an inspiring source for Readers, addressing them to additional literature for an expanded information on specific topics of more interest.

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Section: Normal and Altered Cell And Tissuesmentioning

confidence: 99%

Light and Autofluorescence, Multitasking Features in Living Organisms

Croce

2021

Photochem

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“…The choice of the activity assay compatible with bilirubin was necessary because a subset of the samples was from patients with biliary disease. Bilirubin shows absorption at 453 nm (Vreman, et al, 2019), which interferes with the absorbance results of the dithionite difference method obtained at 450 nm (De Bock, et al, 2014). The NADPH cytochrome P450 reductase method relies on measurement of absorbance at a different wavelength (550 nm) and was therefore preferred (Matsubara, et al, 1976;Omura & Sato, 1964), and was used as previously described (Achour, et al, 2011;Guengerich, et al, 2009).…”

Section: Nadph Cytochrome P450 Reductase Activitymentioning

confidence: 99%

Scaling Factors for Clearance in Adult Liver Cirrhosis

et al. 2020

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In-vitro in-vivo extrapolation (IVIVE) enables prediction of in vivo clinical outcomes related to drug exposure in various populations from in vitro data. Prudent IVIVE requires scalars specific to the biological characteristics of the system in each population. This study determined experimentally, for the first time, scalars in liver samples from patients with varying degrees of cirrhosis. Microsomal and cytosolic fractions were extracted from 13 noncirrhotic and 32 cirrhotic livers (6 mild, 13 moderate, and 13 severe, based on Child-Pugh Score). Fractional protein content was determined and cytochrome P450 reductase activity was used to correct for microsomal protein loss. Although the median microsomal protein per gram liver (MPPGL) in mild, moderate, and severe cirrhosis (26.2, 32.4, and 30.8 mg.g-1 , respectively) seemed lower than control livers (36.6 mg.g-1), differences were not statistically significant (Kruskal-Wallis test, p>0.05). Corresponding values for cytosolic protein per gram liver (CPPGL) were 88.2, 67.9, 62.2 and 75.4 (mg.g-1) for mild, moderate, sever cirrhosis and control livers, respectively, with statistically lower values for server vs controls (Mann-Whitney p=0.006). Cirrhosis associated with cancer showed lower MPPGL (24.8 mg.g-1) than cirrhosis associated with cholestasis (38.3 mg.g-1 , p=0.003). Physiologicallybased pharmacokinetic simulations with disease-specific scalars captured cirrhosis impact on exposure to afentanil, metoprolol, midazolam, and ethinylestradiol. These experimentallydetermined scalars should alleviate the need for indirect scaling using functional liver volume. Scaling factors in cirrhosis might be a reflection of the etiology rather than the disease severity. Hence, bundling various cirrhotic conditions under the same umbrella when predicting hepatic impairment impact should be revisited. Significance statement: Cirrhosis-specific scalars required for extrapolation from microsomal or cytosolic in vitro systems to liver tissue are lacking. These scalars can help in This article has not been copyedited and formatted. The final version may differ from this version.

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“…max. ∼450 nm) 9 undergoes configurational isomerizations to (Z,E)-and (E,Z)isomers (Scheme 1), both of which can further isomerize to give the (E,E)-configurational isomer. In addition, (E,Z)-and (E,E)-isomers undergo solvent-assisted structural rearrangement to give lumirubin upon irradiation.…”

Section: ■ Introductionmentioning

confidence: 99%

Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit

et al. 2020

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Phototherapy is a standard treatment for severe neonatal jaundice to remove toxic bilirubin from the blood. Here, the wavelength-dependent photochemistry of vinylneoxanthobilirubic acid methyl ester, a simplified model of a bilirubin dipyrrinone subunit responsible for a lumirubin-like structural rearrangement, was thoroughly investigated by liquid chromatography and mass and absorption spectroscopies, with the application of a multivariate curve resolution analysis method supplemented with quantum chemical calculations. Irradiation of the model chromophore leads to reversible Z → E photoisomerization followed by reversible photocyclization to a sevenmembered ring system (formed as a mixture of diastereomers). Both the isomerization processes are efficient (Φ ZE ∼ Φ EZ ∼ 0.16) when irradiated in the wavelength range of 360−410 nm, whereas the E-isomer cyclization (Φ c = 0.006−0.008) and cycloreversion (Φ −c = 0.002−0.004) reactions are significantly less efficient. The quantum yields of all processes were found to depend strongly on the wavelength of irradiation, especially when lower energy photons were used. Upon irradiation in the tail of the absorption bands (490 nm), both the isomers exhibit more efficient photoisomerization (Φ ZE ∼ Φ EZ ∼ 0.30) and cyclization (Φ c = ∼0.07). In addition, the isomeric bilirubin dipyrrinone subunits were found to possess important antioxidant activities while being substantially less toxic than bilirubin.

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The effect of light wavelength on in vitro bilirubin photodegradation and photoisomer production

Cited by 24 publications

References 41 publications

Light and Autofluorescence, Multitasking Features in Living Organisms

Light and Autofluorescence, Multitasking Features in Living Organisms

Scaling Factors for Clearance in Adult Liver Cirrhosis

Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit

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