Chiroptical properties of bilirubin-serum albumin binding sites

Chirality

Volumn 25, Issue 4, 2013, Pages 257-263

  Goncharova, Iryna ^a   Orlov, Sergey ^a   Urbanová, Marie ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

bilirubin; bilirubin albumin interaction; circular dichroism; mammalian serum albumin; stereoselective recognition

Indexed keywords

ALBUMIN; BILIRUBIN; BOVINE SERUM ALBUMIN; HUMAN SERUM ALBUMIN;

ALBUMIN BLOOD LEVEL; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BILIRUBIN BLOOD LEVEL; CHIRALITY; DRUG BINDING SITE; HUMAN; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONFORMATION;

EID: 84875645276     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22143     Document Type: Article

References (44)

1. Hansen TWR, Bradtlid D,. Bilirubin and brain toxicity. Acta Paediatr Scand 1986; 75: 513-522.
2. McDonagh AF, Lightner DA,. 'Like a shrivelled blood orange'-bilirubin, jaundice, and phototherapy. Pediatrics 1985; 75 (3): 443-455.
3. Ostrow JD, Pascolo L, Tiribelli C,. Mechanisms of bilirubin neurotoxicity. Hepatology 2002; 35: 1277-1280.
4. Boiadjiev SE, Lightner DA,. Optical activity and stereochemistry of linear oligopyrroles and bile pigments. Tetrahedron Asymmetry 1999; 10: 607-655.
5. Le Bas G, Allegret A, Mauguen Y, de Rango C, Bailly M,. The structure of triclinic bilirubin chloroform-methanol solvate. Acta Crystallogr Sect B 1980; 36: 3007-3011.
6. Brodersen R,. Bilirubin transport in the newborn infant, reviewed with relation to kernicterus. J Pediatr 1980; 96: 349-356.
7. Vítek L, Ostrow JD,. Bilirubin chemistry and metabolism; harmful and protective aspects. Curr Pharm Des 2009; 15: 2869-2883.
8. Brito AM, Silva RFM, Brites D,. Bilirubin toxicity to human erythrocytes: a review. Clin Chim Acta 2006; 374: 46-56.
9. Shapiro SM,. Bilirubin toxicity in the developing nervous system. Pediatr Neurol 2003; 29: 410-421.
10. Neuzil J, Stocker R,. Free and albumin-bound bilirubin are efficient co-antioxidants for α- tocopherol, inhibiting plasma and low density lipoprotein lipid peroxidation. J Biol Chem 1994; 269: 16712-16719.
11. Bernhard K, Ritzel G, Steiner KU,. Uber eine biologische Bedeutung der Gallenfarbstoffe. Bilirubin und Biliverdin als Antioxidation duer das Vitamin A und die essentiellen Fettsaeuren. Helv Chim Acta 1954; 37: 306-313.
12. Bulmer AC, Ried K, Coombes JS, Blanchfield JT, Toth I, Wagner KH,. The anti-mutagenic and antioxidant effects of bile pigments in the Ames Salmonella test. Mutat Res 2007; 629: 122-132.
13. Gopinathan V., Bilirubin and ascorbate antioxidant activity in neonatal plasma. FEBS Lett 1994; 349: 197-200.
14. Sedlak TW, Snyder SH,. Bilirubin benefits: cellular protection by a biliverdin reductase antioxidant cycle. Pediatrics 2004; 113: 1776-1782.
15. Stocker R., Antioxidant activities of bile pigments. Antioxid Redox Signal 2004; 6: 841-849.
16. Stocker R, Glazer AN, Ames BN,. Antioxidant activity of albumin-bound bilirubin. Proc Natl Acad Sci U S A 1987; 84: 5918-5922.
17. Arriaga SM, Almara AM, Mottino AD,. In vivo anti-complement effect of bilirubin-IXα. Biochem Pharmacol 2002; 64: 741-744.
18. Jameel NM, Frey BM, Frey FJ, Gowda TV, Vishwanath BS,. Inhibition of secretory phospholipase A2 enzyme by bilirubin: a new role as endogenous anti-inflammatory molecule. Mol Cell Biochem 2005; 276: 219-225.
19. Bulmer AC, Ried K, Blanchfield JT, Wagner KH,. The anti-mutagenic properties of bile pigments. Mutat Res 2008; 658: 28-41.
20. Mukerjee P, Ostrow JD,. Interactions of unconjugated bilirubin with vesicles, cyclodextrins and micelles: new modeling and the role of high pKa values. BMC Biochem 2010; 11. Available at: http://www.biomedcentral.com/1471- 2091/11/16.
21. Hahm JS, Ostrow JD, Mukerjee P, Celic L,. Ionization and self-association of unconjugated bilirubin, determined by rapid solvent partition from chloroform, with further studies of bilirubin solubility. J Lipid Res 1992; 33: 1123-1137.
22. Frei B, Stocker R, Ames BN,. Antioxidant defenses and lipid peroxidation in human blood plasma. Proc Natl Acad Sci U S A 1988; 85: 9748-9752.
23. Brodersen R., Binding of bilirubin to albumin. CRC Crit Rev Clin Lab Sci 1980; 11 (4): 305-399.
24. Jacobsen J, Brodersen R,. Albumin-bilirubin binding mechanism. Kinetic and spectroscopic studies of binding of bilirubin and xanthobilirubic acid to human serum albumin. J Biol Chem 1983; 258: 6319-6326.
25. Knudsen A, Pedersen AO, Brodersen R,. Spectroscopic properties of bilirubin-human serum albumin complexes: a stoichiometric analysis. Arch Biochem Biophys 1986; 244: 273-284.
26. Peters Jr T,. Serum albumin. Adv Protein Chem 1985; 37: 161-245.
27. Eichinger D, Falk H,. On the chemistry of pyrrole pigments, XLIV: Bile pigments as ionophores. Monatsh Chem 1982; 113: 355-364.
28. Lightner DA, Reisinger M, Landen GL,. On the structure of albumin-bound bilirubin. Selective binding of intramolecularly hydrogen-bonded conformational enantiomers. J Biol Chem 1986; 261: 6034-6038.
29. Petersen CE, Ha CE, Harohalli K, Feix JB, Bhagavan NV,. A dynamic model for bilirubin binding to human serum albumin. J Biol Chem 2000; 275: 20985-20995.
30. Blaha G, Siam M, Lehner H,. A circular dichroism (CD) study of the consecutive binding of serum albumin to bilirubin. Possible implications for the bilirubin level. J Chem Soc Perkin Trans 2 1997: 2119-2124.
31. Goncharova I, Urbanová M,. Stereoselective bile pigment binding to polypeptides and albumins: a circular dichroism study. Anal Bioanal Chem 2008; 392: 1355-1365.
32. Khan MM, Muzammil S, Tayyab S,. Role of salt bridge(s) in the binding and photoconversion of bilirubin bound to high affinity site on human serum albumin. Biochim Biophy Acta 2000; 1479: 103-113.
33. Khan MM, Tayyab S,. Understanding the role of internal lysine residues of serum albumins in conformational stability and bilirubin binding. Biochim Biophys Acta 2001; 1545: 263-277.
34. Siam M, Blaha G, Lehner H,. Maximum binding capacity of serum albumin for bilirubin is one, as revealed by circular dichroism. J Chem Soc Perkin Trans 2 1998: 853-856.
35. Amin SB, Ahlfors CE,. Bilirubin-binding capacity in premature infants. Pediatrics 2008; 121: 872-873.
36. Brodersen R, Funding L, Pedersen AO, Röigaard-Petersen H,. Binding of bilirubin to low-affinity sites of human serum albumin in vitro followed by co-crystallization. Scand J Clin Lab Invest 1972; 29: 433-446.
37. Carter DC, Ho JX,. Structure of serum albumin. Adv Protein Chem 1994; 45: 153-203.
38. He XM, Carter DC,. Atomic structure and chemistry of human serum albumin. Nature 1992; 358: 209-215.
39. Person RV, Peterson BR, Lightner DA,. Bilirubin conformational analysis and circular dichroism. J Am Chem Soc 1994; 116 (1): 42-59.
40. Wang J, Ndou TT, Warner IM, Pau CP,. Spectroscopic analysis and drug-binding studies of the CNBr fragments of human serum albumin. Talanta 1993; 40: 557-563.
41. Goncharova I, Urbanová M,. Bile pigment complexes with cyclodextrins: electronic and vibrational circular dichroism study. Tetrahedron Asymmetry 2007; 18: 2061-2068.
42. Abbate S, Lebon F, Longhi G, Boiadjiev SE, Lightner DA,. Vibrational and electronic circular dichroism of dimethyl mesobilirubins-XIIIα. J Phys Chem B 2012; 116: 5628-5636.
43. Zunszain PA, Ghuman J, McDonagh AF, Curry S,. Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXα. J Mol Biol 2008; 381: 394-406.
44. Minomo A, Ishima Y, Kragh-Hansen U, Chuang VTG, Uchida M, Taguchi K, Watanabe H, Maruyama T, Morioka H, Otagiri M,. Biological characteristics of two lysines on human serum albumin in the high-affinity binding of 4Z,15Z-bilirubin-IXα revealed by phage display. FEBS J 2011; 278: 4100-4111.