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Chemical Compound Review

AC1O6F66     3-[2-[[3-(2-carboxyethyl)-5- [(Z)-(3...

Synonyms:
 
 
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Disease relevance of bilirubin

 

High impact information on bilirubin

  • Kinetics and mechanism of electron transfer in intact photosystem II and in the isolated reaction center: Pheophytin is the primary electron acceptor [6].
  • If the reaction centers are prepared in the dark redox state P-700 A X FdB-FdA-, then upon illumination at 11K we observe a different triplet species of uncertain origin, possibly pheophytin or carotenoid [7].
  • Primary charge separation in bacterial photosynthesis: oxidized chlorophylls and reduced pheophytin [8].
  • This indicates that Cu(II) does not affect the electron transport between P680 and pheophytin [9].
  • Photosynthetic reaction center protein D1 contains five membrane-spanning alpha-helices which form binding sites for pheophytin, chlorophyll, carotenoids, quinone, Fe2+, and probably Mn2+ [10].
 

Chemical compound and disease context of bilirubin

  • To assess the diagnostic value of fasting serum total bile acids (STBA) in liver disease, STBA together with serum bilirubin (BIL), serum alkaline phosphatase (AP), and serum aspartate aminotransferase (ASAT) were measured in 66 consecutive patients who had a liver biopsy [5].
  • The experiments were performed in intact cells of the cyanobacterium Synechocystis 6803 in which the redox properties of the primary pheophytin electron acceptor, Phe, the primary electron donor, P(680), and the first quinone electron acceptor, Q(A), were modified [11].
  • In contrast, synchrony of total algal abundance was low (beta-carotene, pheophytin a, S < 0.10), reflecting low interannual coherence of summer taxa including colonial cyanobacteria and chlorophytes [12].
 

Biological context of bilirubin

  • Experimental evidence suggests that induction of the HO system is an important endogenous mechanism for cytoprotection and that the downstream products of heme degradation, CO, BR, and BV, may mediate these powerful beneficial effects [13].
  • 99mTc-DISIDA Vo was inhibited by BR, BSP, ICG and RB, as well as by a rabbit antibody to the rat liver plasma membrane BSP/BR binding protein [14].
  • The 15N content of pheophytin, the magnesium-free derivative of chlorophyll, can be measured with great accuracy and precision using positive-ion atmospheric pressure ionization electrospray mass spectroscopy following a simple solvent extraction of small amounts of plant tissue [4].
  • Pheophytin a also enhanced signal transduction in the mitogen-activated protein kinase signaling pathway, which is also induced by nerve growth factor [15].
  • Recently, a chlorophyll-related compound, pheophytin a, has been identified from an edible green alga, Enteromorpha prolifera (Sujiao-nori in Japanese) as a potent suppressive substance against genotoxin-induced umu C gene expression in a tester bacteria (Okai and Higashi-Okai, 1997, J. Sci. Food Agricul. 71, 531-535) [16].
 

Anatomical context of bilirubin

 

Associations of bilirubin with other chemical compounds

  • RESULTS: Associations were found between UGT enzyme activities of bilirubin (B) and 4-nitrophenol (NP; r=0.47, P=0.0024), B and 4-methylumbelliferone (MUB; r=0.54, P=0.0003), and NP and MUB (r=0.89, P<0.0001) [19].
  • In fact, recent work has demonstrated that administration of exogenous CO, BR, or BV may offer a simple, inexpensive method to substitute for the cytoprotective effects of HO-1 in a variety of clinically applicable models [13].
  • The dynamics of the elementary electron transfer step between pheophytin and primary ubiquinone in bacterial photosynthetic reaction centers is investigated by using a discrete state approach, including only the intramolecular normal modes of vibration of the two redox partners [20].
  • HPLC monitoring showed that pheophytin agradual degradation (> 90%) was accompanied by a considerable alpha-tocopherol loss (22-35%) due to the reaction of the latter with singlet oxygen [21].
  • Our results demonstrate that BR action induces a decrease in DPH and TMA-DPH polarization, FR increases DPH and TMA-DPH polarization, and CR causes only an increase in TMA-DPH polarization in lysosomal membranes [22].
 

Gene context of bilirubin

  • However, these associations were not found in GGT, ALP, or BIL [23].
  • The effect of pheophytin a on neurite outgrowth of PC12 cells was completely blocked by U0126, a representative mitogen-activated protein kinase kinase inhibitor [15].
  • We show that the method is very sensitive for the detection of contaminants such as the core antenna protein CP47, pigment-free and denatured reaction center proteins, and unbound chlorophyll and pheophytin molecules [24].
  • Pigment stoichiometries were determined using two different methods of data analysis and were based on the assumption that there are two pheophytin a molecules per photosystem II reaction center [17].
  • The Delta mu values for the Q(x) and Q(y) transitions of H(B) are small (Delta mu = 0.6-1.0 D f(-1)), whereas that of the Q(x) transition of the active pheophytin H(A) is remarkably large (Delta mu = 3 D f(-1)) [25].
 

Analytical, diagnostic and therapeutic context of bilirubin

  • Pigment analysis using reverse-phase HPLC confirmed that contamination by chlorophyll bound to the CP47 apoprotein in the nonresolved RC preparation was low and that the ratio of chlorophyll a to pheophytin a remained 6 when the preparation was separated into its monomeric and dimeric components [26].
  • Pheophytin-protein interactions in photosystem II studied by resonance Raman spectroscopy of modified reaction centers [27].
  • The efficacy of this device was compared with that of conventional phototherapy devices by measuring the in vitro photodegradation of BR in human serum albumin [28].
  • It is concluded that STBA had no diagnostic advantage as compared with the commonly used liver function tests BIL, AP, and ASAT [5].
  • Hemoperfusion through albumin-conjugated agarose gel (AAG) effectively removes bilirubin (BR) and other albumin-bound materials from whole blood or plasma [29].

References

  1. Formation of a long-lived P+BA- state in plant pheophytin-exchanged reaction centers of Rhodobacter sphaeroides R26 at low temperature. Kennis, J.T., Shkuropatov, A.Y., van Stokkum, I.H., Gast, P., Hoff, A.J., Shuvalov, V.A., Aartsma, T.J. Biochemistry (1997) [Pubmed]
  2. Isolation and spectroscopic characterization of a plantlike photosystem II reaction center from the cyanobacterium Synechocystis sp. 6803. Oren-Shamir, M., Sai, P.S., Edelman, M., Scherz, A. Biochemistry (1995) [Pubmed]
  3. Orientation of the tyrosyl D, pheophytin anion, and semiquinone Q(A)(*)(-) radicals in photosystem II determined by high-field electron paramagnetic resonance. Dorlet, P., Rutherford, A.W., Un, S. Biochemistry (2000) [Pubmed]
  4. A mass spectrometry method for measuring 15N incorporation into pheophytin. Kahn, M.L., Parra-Colmenares, A., Ford, C.L., Kaser, F., McCaskill, D., Ketchum, R.E. Anal. Biochem. (2002) [Pubmed]
  5. The diagnostic value of fasting serum total bile acid concentration in patients with suspected liver disease. A prospective, consecutive study. Rickers, H., Christensen, M., Arnfred, T., Dige, U., Thaysen, E.H. Scand. J. Gastroenterol. (1982) [Pubmed]
  6. Kinetics and mechanism of electron transfer in intact photosystem II and in the isolated reaction center: Pheophytin is the primary electron acceptor. Holzwarth, A.R., Müller, M.G., Reus, M., Nowaczyk, M., Sander, J., Rögner, M. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  7. Triplet states in photosystem I of spinach chloroplasts and subchloroplast particles. Frank, H.A., McLean, M.B., Sauer, K. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  8. Primary charge separation in bacterial photosynthesis: oxidized chlorophylls and reduced pheophytin. Fajer, J., Brune, D.C., Davis, M.S., Forman, A., Spaulding, L.D. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  9. Precise location of the Cu(II)-inhibitory binding site in higher plant and bacterial photosynthetic reaction centers as probed by light-induced absorption changes. Yruela, I., Alfonso, M., Ortiz de Zarate, I., Montoya, G., Picorel, R. J. Biol. Chem. (1993) [Pubmed]
  10. Ribosomes pause at specific sites during synthesis of membrane-bound chloroplast reaction center protein D1. Kim, J., Klein, P.G., Mullet, J.E. J. Biol. Chem. (1991) [Pubmed]
  11. Radiative and non-radiative charge recombination pathways in Photosystem II studied by thermoluminescence and chlorophyll fluorescence in the cyanobacterium Synechocystis 6803. Cser, K., Vass, I. Biochim. Biophys. Acta (2007) [Pubmed]
  12. Century-long synchrony of fossil algae in a chain of Canadian prairie lakes. Patoine, A., Leavitt, P.R. Ecology (2006) [Pubmed]
  13. Products of heme oxygenase and their potential therapeutic applications. Kirkby, K.A., Adin, C.A. Am. J. Physiol. Renal Physiol. (2006) [Pubmed]
  14. Studies of the hepatocellular uptake of the hepatobiliary scintiscanning agent 99mTc-DISIDA. Okuda, H., Nunes, R., Vallabhajosula, S., Strashun, A., Goldsmith, S.J., Berk, P.D. J. Hepatol. (1986) [Pubmed]
  15. Pheophytin a, a low molecular weight compound found in the marine brown alga Sargassum fulvellum, promotes the differentiation of PC12 cells. Ina, A., Hayashi, K., Nozaki, H., Kamei, Y. Int. J. Dev. Neurosci. (2007) [Pubmed]
  16. Potent anti-inflammatory activity of pheophytin a derived from edible green alga, Enteromorpha prolifera (Sujiao-nori). Okai, Y., Higashi-Okai, K. Int. J. Immunopharmacol. (1997) [Pubmed]
  17. Pigment quantitation and analysis by HPLC reverse phase chromatography: a characterization of antenna size in oxygen-evolving photosystem II preparations from cyanobacteria and plants. Patzlaff, J.S., Barry, B.A. Biochemistry (1996) [Pubmed]
  18. Potent suppressive activity of pheophytin a and b from the non-polyphenolic fraction of green tea (Camellia sinensis) against tumor promotion in mouse skin. Higashi-Okai, K., Otani, S., Okai, Y. Cancer Lett. (1998) [Pubmed]
  19. Combined polymorphisms in UDP-glucuronosyltransferases 1A1 and 1A6: implications for patients with Gilbert's syndrome. Peters, W.H., te Morsche, R.H., Roelofs, H.M. J. Hepatol. (2003) [Pubmed]
  20. Role of intramolecular vibrations in long-range electron transfer between pheophytin and ubiquinone in bacterial photosynthetic reaction centers. Borrelli, R., Di Donato, M., Peluso, A. Biophys. J. (2005) [Pubmed]
  21. Stability of virgin olive oil. 2. Photo-oxidation studies. Psomiadou, E., Tsimidou, M. J. Agric. Food Chem. (2002) [Pubmed]
  22. Effects of some biologically active compounds on phagosome-lysosome fusion in peritoneal macrophages of mice. Mozhenok, T., Belyaeva, T., Bulychev, A., Kuznetsova, I., Leontieva, E., Faddejeva, M. Cell Biol. Int. (1998) [Pubmed]
  23. Serum liver function profiles in coking workers. Wu, M.T., Mao, I.F., Wypij, D., Ho, C.K., Chen, J.R., Christiani, D.C. Am. J. Ind. Med. (1997) [Pubmed]
  24. Purification and spectroscopic characterization of photosystem II reaction center complexes isolated with or without Triton X-100. Eijckelhoff, C., van Roon, H., Groot, M.L., van Grondelle, R., Dekker, J.P. Biochemistry (1996) [Pubmed]
  25. Electric field effects on the chlorophylls, pheophytins, and beta-carotenes in the reaction center of photosystem II. Frese, R.N., Germano, M., de Weerd, F.L., van Stokkum, I.H., Shkuropatov, A.Y., Shuvalov, V.A., van Gorkom, H.J., van Grondelle, R., Dekker, J.P. Biochemistry (2003) [Pubmed]
  26. Heterogeneity and pigment composition of isolated photosystem II reaction centers. Zheleva, D., Hankamer, B., Barber, J. Biochemistry (1996) [Pubmed]
  27. Pheophytin-protein interactions in photosystem II studied by resonance Raman spectroscopy of modified reaction centers. Germano, M., Pascal, A., Shkuropatov, A.Y., Robert, B., Hoff, A.J., van Gorkom, H.J. Biochemistry (2002) [Pubmed]
  28. Light-emitting diodes: a novel light source for phototherapy. Vreman, H.J., Wong, R.J., Stevenson, D.K., Route, R.K., Reader, S.D., Fejer, M.M., Gale, R., Seidman, D.S. Pediatr. Res. (1998) [Pubmed]
  29. Hemoperfusion through albumin-conjugated agarose gel for the treatment of neonatal jaundice in premature rhesus monkeys. Scharschimidt, B.F., Martin, J.F., Shapiro, L.J., Plotz, P.H., Berk, P.D. J. Lab. Clin. Med. (1977) [Pubmed]
 
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