Photonics of bilirubin – biologically important molecule (Review)

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Bilirubin, a bile pigment having photochemical activity, plays an important role in the body. Photonics (photophysics and photochemistry) of bilirubin has attracted scientific and practical interest of researchers up to the present day. This is because its molecule is capable of ultrafast photoisomerization processes, and also contains two interacting dipyrromethenone chromophores. Furthermore, the photochemical reactions of bilirubin are used in the widespread phototherapy of neonatal jaundice (neonatal hyperbilirubinemia), carried out to reduce the level of bilirubin in the body. This review briefly considers photonics of bilirubin, as well as its main photochemical reactions in phototherapy of neonatal hyperbilirubinemia.

Full Text

Restricted Access

About the authors

A. S. Tatikolov

Emanuel Institute of Biochemical Physics, Russian Academy of Sciences

Author for correspondence.
Email: tatikolov@mail.ru
Russian Federation, Moscow

I. G. Panova

International Scientific and Practical Center of Tissue Proliferation

Email: tatikolov@mail.ru
Russian Federation, Moscow

References

  1. S.Y. Kim and S.C. Park, Front. Pharmacol. 3, 45 (2012). https://doi.org/10.3389/fphar.2012.00045
  2. E. Sticova and M. Jirsa, World J. Gastroenterol. 19, 6398 (2013). https://doi.org/10.3748/wjg.v19.i38.6398
  3. S. Itoh, H. Okada, K. Koyano, S. Nakamura, Y. Konishi, T. Iwase, and T. Kusaka, Front. Pediatr. 10, 1002408 (2023). https://doi.org/10.3389/fped.2022.1002408
  4. D.A. Lightner and A.F. McDonagh, Acc. Chem. Res. 17, 417 (1984). https://doi.org/10.1021/ar00108a002
  5. C.P. Soto Conti, Arch. Argent. Pediatr. 119, No. 1, e18 (2021). http://dx.doi.org/10.5546/aap.2021.eng.e18
  6. J.F. Creeden, D.M. Gordon, D.E. Stec, and T.D. Hinds Ir, Am. J. Physiol. Endocrinol. Metab. 320, E191 (2021). https://doi.org/10.1152/ajpendo.00405.2020
  7. A.A. Lamola, Effects of environment on photophysical processes of bilirubin. In: Optical Properties and Structure of Terrapyrroles. Edited by G. Blauer and H. Sund. Walter de Gruyter, Berlin, 1985, p. 311–326.
  8. D.A. Lightner, J.K. Gawronski, and W.M.D. Wijekoon, J. Am. Chem. Soc. 109, No. 21, 6354 (1987). https://doi.org/10.1021/ja00255a020
  9. A.F. McDonagh and D.A. Lightner, Pediatrics 75, 443 (1985). https://doi.org/10.1542/peds.75.3.443
  10. A.F. McDonagh and D.A. Lightner, Semin. Liver Dis. 8, 272 (1988). https://doi.org/10.1055/s-2008-1040549
  11. J.E. Ennever, Pediatr. Clin. North Am. 33, 603 (1986). https://doi.org/10.1016/S0031-3955(16)36045-X
  12. D.A. Lightner, M. Reisinger, and G.L. Landen, J. Biol. Chem. 261, No. 13, 6034 (1986). https://doi.org/10.1016/S0021-9258(17)38489-2
  13. M. Taniguchi and J.S. Lindsey, J. Photochem. Photobiol. C 55, 100585 (2023). https://doi.org/10.1016/j.jphotochemrev.2023.100585
  14. A.A. Lamola and J. Flores, J. Am. Chem. Soc. 104, No. 9, 2530 (1982). https://doi.org/10.1021/ja00373a033
  15. B. Zietz and T. Gillbro, J. Phys. Chem. B 111, 11997 (2007). https://doi.org/10.1021/jp073421c
  16. A.S. Vetchinkin, S.Ya. Umanskii, Yu.A. Chaikina, and A.I. Shushin, Russ. J. Phys. Chem. B 16, No. 5, 945 (2022). https://doi.org/10.1134/S1990793122050104
  17. D.R. Anfimov, I.S. Golyak, O.A. Nebritova, and I.L. Fufurin, Russ. J. Phys. Chem. B 16, No. 5, 834 (2022). https://doi.org/10.1134/s1990793122050165
  18. V. Gorokhov, P. Knox, B. Korvatovskiy, N.Kh. Seifullina, S.N. Goryachev, N.P. Grishanova, V.Z. Paschenko, and A. B. Rubin, Russ. J. Phys. Chem. B 17, No. 3, 571 (2023). https://doi.org/10.1134/S199079312303020X
  19. D.A. Cherepanov, G.E. Milanovsky, V.A. Nadtochenko, and A.Yu. Semenov, Russ. J. Phys. Chem. B 17, No. 3, 594 (2023). https://doi.org/10.1134/S1990793123030193
  20. C. Carreira-Blanco, P. Singer, R. Diller, and J.L.P. Lustres, Phys. Chem. Chem. Phys. 18, 7148 (2016). https://doi.org/10.1039/c5cp06971h
  21. H.P. Upadhyaya, J. Phys. Chem. A 122, No. 46, 9084 (2018). https://doi.org/10.1021/acs.jpca.8b09392
  22. R. Pu, Z. Wang, R. Zhu, J. Jiang, T.-C. Weng, Y. Huang, and W. Liu, J. Phys. Chem. Lett. 14, 809 (2023). https://doi.org/10.1021/acs.jpclett.2c03535
  23. E.J. Land, Photochem. Photobiol. 24, 475 (1976). https://doi.org/10.1111/j.1751-1097.1976.tb06857.x
  24. V.Yu. Plavskii, A.I. Tretyakova, L.G. Plavskaya, A.V. Mikulich, A.S. Stashevskii, A.S. Grabchikov, I.A. Khodasevich, and V.A. Orlovich, Molecular, membrane and cellular basis of the functioning of biosystems: Int. Scientific Conf. Tenth Congress of the Belarusian Public Association of Photobiologists and Biophysicists, June 19–21, 2012, Minsk, Belarus: Books of Art. in 2 books. Book 2. Editorial board: I.D. Volotovskii, S.N. Cherenkevich, et al. Minsk: Publishing house Center of BSU, 2012. P. 71, ISBN 978-985-553-356-7.
  25. R.W. Sloper and T.G. Truscott, Photoсhem. Photobiol. 35, 743 (1982). https://doi.org/10.1111/j.1751-1097.1982.tb02640.x
  26. K.L. Tan, Clin. Perinatol. 18, No. 3, 423 (1991). https://doi.org/10.1016/S0095-5108(18)30506-2
  27. F. Ebbesen, H.J. Vreman, and T.W.R. Hansen, Int. J. Mol. Sci. 24, 461 (2023). https://doi.org/10.3390/ijms24010461
  28. T.M. Slusher, H.J. Vreman, A.M. Brearley, Y.E. Vaucher, R.J. Wong, D.K. Stevenson, O.T. Adeleke, I.P. Ojo, G. Edowhorhu, T.C. Lund, and D.A. Gbadero, Lancet Glob. Health 6, e1122 (2018). http://dx.doi.org/10.1016/S2214-109X(18)30373-5
  29. S. Onishi, S. Itoh, and K. Isobe, Biochem. J. 236, 23 (1986). https://doi.org/10.1042/bj2360023
  30. S. Itoh, S. Onishi, K. Isobe, M. Manabe, and T. Yamakawa, Biol. Neonate 51, 10 (1987). https://doi.org/10.1159/000242625
  31. S. Itoh, H. Okada, T. Kuboi, and T. Kusaka, Pediatr. Intern. 59, 959 (2017). https://doi.org/10.1111/ped.13332
  32. Y. Uchida, Y. Morimoto, T. Uchiike, T. Kamamoto, T. Hayashi, I. Arai, T. Nishikubo, and Y. Takahashi, Early Human Dev. 91, 381 (2015). http://dx.doi.org/10.1016/j.earlhumdev.2015.04.010
  33. F. Ebbesen, P. Madsen, S. Støvring, H. Hundborg, and G. Agati, Acta Pædiatr. 96, 837 (2007). https://doi.org/10.1111/j.1651-2227.2007.00261.x
  34. F. Ebbesen, P.K. Vandborg, and M.L. Donneborg, Seminars in Perinatol. 45, 151358 (2021). https://doi.org/10.1016/j.semperi.2020.151358
  35. F. Ebbesen, M. Rodrigo-Domingo, A.M. Moeller, H.J. Vreman, and M.L. Donneborg, Pediatr. Res. 89, 598 (2021). https://doi.org/10.1038/s41390-020-0911-9
  36. F. Ebbesen, P.H. Madsen, P.K. Vandborg, L.H. Jakobsen, T. Trydal, and H.J. Vreman, Pediatr. Res. 80, 511 (2016). https://doi.org/10.1038/pr.2016.115
  37. A.A. Lamola, Clin. Perinatol. 43, No. 2, 259 (2016). http://dx.doi.org/10.1016/j.clp.2016.01.004
  38. V.K. Bhutani, Pediatrics. 128, e1046 (2011). www.pediatrics.org/cgi/doi/10.1542/peds.2011-1494

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Fig. 1. Structure of the BR molecule.

Download (26KB)
Indexing metadata
3. Fig. 2. Structure of the Z,Z-conformation of BR – 4Z,15Z-bilirubin-IXα. Dashed lines show intramolecular hydrogen bonds stabilizing the Z,Z-conformation. Arrows point to double bonds 4–5 and 15–16, relative to which BR photoisomerization occurs.

Download (50KB)
Indexing metadata
4. Fig. 3. Structure of lumirubin (cyclobilirubin).

Download (28KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences