79719-28-1Relevant academic research and scientific papers
On the Preparation of Bilirubins of the Natural α Series Substituted with a Propionic Acid Residue and a Hydroxypropyl Group [1]
Crusats,Farrera,Ribo
, p. 85 - 89 (1996)
The reduction of mesobiliverdin XIIIα propan-1,3-diyl diester with NaBH4 affords mesobilirubin XIIIα propan-1,3-diyl diester. The same reduction of mesobiliverdin XIIIα methylen diester. The same reduction of mesobiliverdin XIIIα methylen diester affords 8-(2-carboxyethyl)-3,17-diethyl-12-(3-hydroxypropyl)-2,7,13,17- tetramethylbiladien-ac-1,9-(21H, 24H)-dione (MBR-mc). The UV/Vis and 1H NMR spectra of MBR-mc show that its structure in solution is similar to that of the natural bilirubins of the α series.
Induction of wavelength-dependent photochemistry in bilirubins by serum albumin
McDonagh, Antony F.,Agati, Giovanni,Lightner, David A.
, p. 649 - 660 (2007/10/03)
Quantum yields for Z ? E photoisomerization of the natural bi-chromophore bilirubin IXα in ammoniacal methanol solution were found to vary with excitation wavelength, whereas no variation (within experimental error) was observed for xanthobilirubic acid and for symmetrically substituted bilirubins (bilirubin IIIα, bilirubin XIIIα, and mesobilirubin XIIα) in the same solvent. The quantum yield for Z ? E photoisomerization of xanthobilirubic acid bound to human serum albumin was also invariant with excitation wavelength. In contrast, quantum yields for Z ? E photoisomerization of the symmetrically-substituted bilirubins did show marked excitation wavelength dependency when they were bound to human serum albumin. These results show that quantum yields for Z ? E photoisomerization of bilirubins are markedly sensitive to protein binding and to the nature of pyrrole ring β-substituents. They also demonstrate that wavelength-dependent photochemistry is characteristic of bilirubins with non-identical pyrromethenone chromophores, as expected from exciton coupling theory, and that complexation with albumin induces wavelength-dependent photochemistry in symmetrically substituted bilirubins.
An efficient synthesis of symmetric bilindiones. Mesobilirubin-XIIIα and analogs with varying alkanoic acid chain lengths
Shrout,Puzicha,Lightner
, p. 328 - 332 (2007/10/02)
An inexpensive gram-scale, three-step procedure is described to convert methyl xanthobilirubinate and it alkanoic acid ester analogs (methyl 5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2- ylidene)methyl]-1,4-dimethylpyrrol-3-ethanoate, -propanoate, -butanoate, -pentanoate, -hexanoate) into mesobilirubin-XIIIα and analogs in >90% yield at each step.
