Lumirubin

Lumirubin
	; (Z)-isomer of lumirubin
Names
	IUPAC name 3-[2-[[6-(2-carboxyethyl)-7,11-dimethyl-12-oxo-4,13-diazatricyclo[8.3.0.03,7]trideca-1,3,5,9-tetraen-5-yl]methyl]-5-[(E)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
Identifiers
CAS Number	110617-57-7; 83664-21-5;
3D model (JSmol)	Interactive image;
ChemSpider	4946083;
PubChem CID	135754285;
	InChI InChI=1S/C33H36N4O6/c1-6-19-16(2)24(36-32(19)43)13-23-17(3)20(7-9-29(38)39)25(34-23)14-27-22(8-10-30(40)41)33(5)12-11-21-18(4)31(42)37-26(21)15-28(33)35-27/h6,11,13,15,18,34H,1,7-10,12,14H2,2-5H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b24-13+ Key: BYVDUQYJIIPFIB-ZMOGYAJESA-N;
	SMILES CC1C2=CCC3(C(=NC(=C3CCC(=O)O)CC4=C(C(=C(N4)/C=C/5\C(=C(C(=O)N5)C=C)C)C)CCC(=O)O)C=C2NC1=O)C;
Properties
Chemical formula	C33H36N4O6
Molar mass	584.673 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lumirubin is a structural isomer of bilirubin, which is formed during phototherapy used to treat neonatal jaundice. This polar isomer resulting from the blue-green lights of phototherapy has an active site to albumin, and its effects are considered less toxic than those of bilirubin.^[1]^[2]^[3] Lumirubin is excreted into bile or urine. ZZ, ZE, EE and EZ are the four structural isomers of bilirubin. ZZ is the stable, more insoluble form. Other forms are relatively soluble and are known as lumirubins. Phototherapy converts the ZZ form into lumirubins. Monoglucuronylated lumirubins are easily excreted.^[4]

References

^ Dvořák, Aleš; Pospíšilová, Kateřina; Žížalová, Kateřina; Capková, Nikola; Muchová, Lucie; Vecka, Marek; Vrzáčková, Nikola; Křížová, Jana; Zelenka, Jaroslav; Vítek, Libor (2021). "The Effects of Bilirubin and Lumirubin on Metabolic and Oxidative Stress Markers". Frontiers in Pharmacology. 12: 567001. doi:10.3389/fphar.2021.567001. ISSN 1663-9812. PMC 7969661. PMID 33746746.
^ Jašprová, Jana; Dvořák, Aleš; Vecka, Marek; Leníček, Martin; Lacina, Ondřej; Valášková, Petra; Zapadlo, Miloš; Plavka, Richard; Klán, Petr; Vítek, Libor (2020-03-10). "A novel accurate LC-MS/MS method for quantitative determination of Z-lumirubin". Scientific Reports. 10 (1): 4411. Bibcode:2020NatSR..10.4411J. doi:10.1038/s41598-020-61280-z. ISSN 2045-2322. PMC 7064611. PMID 32157102. S2CID 212641930.
^ Jasprova, Jana; Matteo Dal Ben; Eleonora Vianello; Iryna Goncharova; Marie Urbanova; Karolina Vyroubalova; Silvia Gazzin; Claudio Tiribelli; Martin Sticha; Marcela Cerna; Libor Vitek (1 February 2016). "The Biological Effects of Bilirubin Photoisomers". PLOS ONE. 11 (2): e0148126. Bibcode:2016PLoSO..1148126J. doi:10.1371/journal.pone.0148126. PMC 4735493. PMID 26829016.
^ Ennever JF, Sobel M, McDonagh AF, Speck WT (July 1984). "Phototherapy for neonatal jaundice: in vitro comparison of light sources". Pediatr. Res. 18 (7): 667–70. doi:10.1203/00006450-198407000-00021. PMID 6540860.

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[1] Dvořák, Aleš; Pospíšilová, Kateřina; Žížalová, Kateřina; Capková, Nikola; Muchová, Lucie; Vecka, Marek; Vrzáčková, Nikola; Křížová, Jana; Zelenka, Jaroslav; Vítek, Libor (2021). "The Effects of Bilirubin and Lumirubin on Metabolic and Oxidative Stress Markers". Frontiers in Pharmacology. 12: 567001. doi:10.3389/fphar.2021.567001. ISSN 1663-9812. PMC 7969661. PMID 33746746.

[2] Jašprová, Jana; Dvořák, Aleš; Vecka, Marek; Leníček, Martin; Lacina, Ondřej; Valášková, Petra; Zapadlo, Miloš; Plavka, Richard; Klán, Petr; Vítek, Libor (2020-03-10). "A novel accurate LC-MS/MS method for quantitative determination of Z-lumirubin". Scientific Reports. 10 (1): 4411. Bibcode:2020NatSR..10.4411J. doi:10.1038/s41598-020-61280-z. ISSN 2045-2322. PMC 7064611. PMID 32157102. S2CID 212641930.

[3] Jasprova, Jana; Matteo Dal Ben; Eleonora Vianello; Iryna Goncharova; Marie Urbanova; Karolina Vyroubalova; Silvia Gazzin; Claudio Tiribelli; Martin Sticha; Marcela Cerna; Libor Vitek (1 February 2016). "The Biological Effects of Bilirubin Photoisomers". PLOS ONE. 11 (2): e0148126. Bibcode:2016PLoSO..1148126J. doi:10.1371/journal.pone.0148126. PMC 4735493. PMID 26829016.

[4] Ennever JF, Sobel M, McDonagh AF, Speck WT (July 1984). "Phototherapy for neonatal jaundice: in vitro comparison of light sources". Pediatr. Res. 18 (7): 667–70. doi:10.1203/00006450-198407000-00021. PMID 6540860.

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[2]

[3]

[4]

Names
(Z)-isomer of lumirubin
IUPAC name 3-[2-[[6-(2-carboxyethyl)-7,11-dimethyl-12-oxo-4,13-diazatricyclo[8.3.0.0^3,7]trideca-1,3,5,9-tetraen-5-yl]methyl]-5-[(E)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
Identifiers
CAS Number	110617-57-7 83664-21-5
3D model (JSmol)	Interactive image
ChemSpider	4946083
PubChem CID	135754285
InChI InChI=1S/C33H36N4O6/c1-6-19-16(2)24(36-32(19)43)13-23-17(3)20(7-9-29(38)39)25(34-23)14-27-22(8-10-30(40)41)33(5)12-11-21-18(4)31(42)37-26(21)15-28(33)35-27/h6,11,13,15,18,34H,1,7-10,12,14H2,2-5H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b24-13+ Key: BYVDUQYJIIPFIB-ZMOGYAJESA-N
SMILES CC1C2=CCC3(C(=NC(=C3CCC(=O)O)CC4=C(C(=C(N4)/C=C/5\C(=C(C(=O)N5)C=C)C)C)CCC(=O)O)C=C2NC1=O)C
Properties
Chemical formula	C₃₃H₃₆N₄O₆
Molar mass	584.673 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references