Tin mesoporphyrin
{{Short description|Compound in biochemistry}}
{{Chembox
| ImageFile = Tin mesoporphyrin.png
| IUPACName = 3-[18-(2-carboxyethyl)-8,13-diethyl-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid;tin(4+);dichloride
|Section1={{Chembox Identifiers
| CASNo = 106344-20-1
| DrugBank = DB04912
| PubChem = 15978579
| UNII = 0KAE1U0G7Q
| StdInChI=1S/C34H38N4O4.2ClH.Sn/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;;;/h13-16H,7-12H2,1-6H3,(H4,35,36,37,38,39,40,41,42);2*1H;/q;;;+4/p-4
| StdInChIKey = LLDZJTIZVZFNCM-UHFFFAOYSA-J
| SMILES = CCC1=C(C2=NC1=CC3=C(C(=C([N-]3)C=C4C(=C(C(=CC5=NC(=C2)C(=C5C)CC)[N-]4)C)CCC(=O)O)CCC(=O)O)C)C.[Cl-].[Cl-].[Sn+4]
}}
|Section2={{Chembox Properties
}}
|Section8={{Chembox Related
}}
}}
Tin mesoporphyrin (SnMP), also known as stannsoporfin, is a metalloporphyrin,{{Citation needed|date=December 2024}} which inhibits heme oxygenase.{{Cite journal |last=Sorrenti |first=Valeria |last2=D’Amico |first2=Agata Grazia |last3=Barbagallo |first3=Ignazio |last4=Consoli |first4=Valeria |last5=Grosso |first5=Salvo |last6=Vanella |first6=Luca |date=2021-06-21 |title=Tin Mesoporphyrin Selectively Reduces Non-Small-Cell Lung Cancer Cell Line A549 Proliferation by Interfering with Heme Oxygenase and Glutathione Systems |url=https://pmc.ncbi.nlm.nih.gov/articles/PMC8235249/ |journal=Biomolecules |language=en |volume=11 |issue=6 |pages=917 |doi=10.3390/biom11060917 |pmc=8235249 |pmid=34205698 |doi-access=free}} It can be used in the treatment of neonatal hyperbilirubinemia.
Structure
As the name, tin mesoporphyrin, suggests, the overall structure is very similar to the naturally occurring heme molecule. It consists of a ring structured protoporphyrin IX molecule that has tin as its central atom.{{cite journal |title = Efficacy and Safety Concerns with Sn-Mesoporphyrin as an Adjunct Therapy in Neonatal Hyperbilirubinemia: A Literature Review| date=2022 | pmc=9314175 | last1=Poudel | first1=P. | last2=Adhikari | first2=S. | journal=International Journal of Pediatrics | volume=2022 | pages=1–7 | doi=10.1155/2022/2549161 | pmid=35898803 | doi-access=free }} As this is a synthetic molecule, the two vinyl groups at both the C2 and C4 positions on the porphyrin macrocyle are reduced to form ethyl groups{{cite journal |title = Tin Mesoporphyrin Selectively Reduces Non-Small-Cell Lung Cancer Cell Line A549 Proliferation by Interfering with Heme Oxygenase and Glutathione Systems| date=2021 | doi=10.3390/biom11060917 | doi-access=free | last1=Sorrenti | first1=Valeria | last2=d'Amico | first2=Agata Grazia | last3=Barbagallo | first3=Ignazio | last4=Consoli | first4=Valeria | last5=Grosso | first5=Salvo | last6=Vanella | first6=Luca | journal=Biomolecules | volume=11 | issue=6 | page=917 | pmid=34205698 | pmc=8235249 }} that is found on tin mesoporphyrin. The molecular weight of tin mesoporphyrin is 754.3 g/mol.{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/Tin-mesoporphyrin |title = Tin-mesoporphyrin}}
Mechanism
In the heme catabolic pathway, heme oxygenase catalyzes the breakdown of heme to biliverdin and well as carbon monoxide that is exhaled. Biliverdin is then converted to bilirubin with biliverdin reductase.{{cite journal |title = Efficacy and Safety Concerns with Sn-Mesoporphyrin as an Adjunct Therapy in Neonatal Hyperbilirubinemia: A Literature Review| date=2022 | pmc=9314175 | last1=Poudel | first1=P. | last2=Adhikari | first2=S. | journal=International Journal of Pediatrics | volume=2022 | pages=1–7 | doi=10.1155/2022/2549161 | pmid=35898803 | doi-access=free }} As high biliverdin levels are usually related to bilirubinemia, tin mesoporphyrin has been found to aid in treatment and prevention of this, primarily in newborn infants. Tin mesoporphyrin competitively inhibits the heme oxygenase enzyme, which prevents the breakdown of heme to biliverdin leading to accumulation of heme and not bilirubin.{{cite journal |title = Efficacy and Safety Concerns with Sn-Mesoporphyrin as an Adjunct Therapy in Neonatal Hyperbilirubinemia: A Literature Review| date=2022 | pmc=9314175 | last1=Poudel | first1=P. | last2=Adhikari | first2=S. | journal=International Journal of Pediatrics | volume=2022 | pages=1–7 | doi=10.1155/2022/2549161 | pmid=35898803 | doi-access=free }}
Application
The application of stannsoporfin or tin mesoporphyrin is currently still being researched.{{Citation needed|date=December 2024}} Clinical studies have outlined its use in the treatment of hyperbilirubinemia infants{{cite journal |title = Tin-mesoporphyrin in the Treatment of Severe Hyperbilirubinemia in a Very-low-birth-weight Infant| date=2003 | doi=10.1038/sj.jp.7210943 | last1=Reddy | first1=Pradeep | last2=Najundaswamy | first2=Shakuntala | last3=Mehta | first3=Rajeev | last4=Petrova | first4=Anna | last5=Hegyi | first5=Thomas | journal=Journal of Perinatology | volume=23 | issue=6 | pages=507–508 | pmid=13679941 | s2cid=19994446 | doi-access=free }} and also the prevention of neonatal jaundice. It has also been found to reduce edema and hematoma in spontaneous intracerebral hemorrhage(ICH) from patients who suffered traumatic brain injuries.{{cite journal |url=https://pubmed.ncbi.nlm.nih.gov/10872746/#:~:text=In%20cerebral%20ischemia%20models%2C%20metalloporphyrins,used%20clinically%20to%20treat%20hyperbilirubinemia. |title = Tin-mesoporphyrin, a potent heme oxygenase inhibitor, for treatment of intracerebral hemorrhage: in vivo and in vitro studies| date=2000 | pmid=10872746 | last1=Wagner | first1=K. R. | last2=Hua | first2=Y. | last3=De Courten-Myers | first3=G. M. | last4=Broderick | first4=J. P. | last5=Nishimura | first5=R. N. | last6=Lu | first6=S. Y. | last7=Dwyer | first7=B. E. | journal=Cellular and Molecular Biology (Noisy-Le-Grand, France) | volume=46 | issue=3 | pages=597–608 }}
= Treatment in hyperbilirubinemia =
In one study, tin mesoporphyrin was administered intramuscularly to a newborn that was only 46 hours old with a low birth weight who had also suffered from severe hyperbilirubinemia.{{cite journal |title = Tin-mesoporphyrin in the Treatment of Severe Hyperbilirubinemia in a Very-low-birth-weight Infant| date=2003 | doi=10.1038/sj.jp.7210943 | last1=Reddy | first1=Pradeep | last2=Najundaswamy | first2=Shakuntala | last3=Mehta | first3=Rajeev | last4=Petrova | first4=Anna | last5=Hegyi | first5=Thomas | journal=Journal of Perinatology | volume=23 | issue=6 | pages=507–508 | pmid=13679941 | s2cid=19994446 | doi-access=free }} Along with blue light treatment, the newborn showed a steady decrease in its total serum biliverdin within 10 hours after administration.{{cite journal |title = Tin-mesoporphyrin in the Treatment of Severe Hyperbilirubinemia in a Very-low-birth-weight Infant| date=2003 | doi=10.1038/sj.jp.7210943 | last1=Reddy | first1=Pradeep | last2=Najundaswamy | first2=Shakuntala | last3=Mehta | first3=Rajeev | last4=Petrova | first4=Anna | last5=Hegyi | first5=Thomas | journal=Journal of Perinatology | volume=23 | issue=6 | pages=507–508 | pmid=13679941 | s2cid=19994446 | doi-access=free }}
= Prevention of neonatal jaundice =
It has also been found that tin mesoporphyrin can aid in the prevention of neonatal jaundice. When administered to pre-discharge newborns who were at risk for neonatal jaundice the results showed a decrease in total biliverdin load, the possibility of postnatal bilirubin progression, as well as the use and duration of phototherapy.{{cite journal |title = Clinical trial of tin mesoporphyrin to prevent neonatal hyperbilirubinemia| date=2016 | doi=10.1038/jp.2016.22 | last1=Bhutani | first1=V. K. | last2=Poland | first2=R. | last3=Meloy | first3=L. D. | last4=Hegyi | first4=T. | last5=Fanaroff | first5=A. A. | last6=Maisels | first6=M. J. | journal=Journal of Perinatology | volume=36 | issue=7 | pages=533–539 | pmid=26938918 | s2cid=205179344 | doi-access=free }}
= Treatment in spontaneous intracerebral hemorrhage =
Tin mesoporphyrin has also been found potentially reduce intracerebral mass in intracerebral hemorrhage cases by decreasing the hematoma and edema volumes.{{cite journal |url=https://pubmed.ncbi.nlm.nih.gov/10872746/ |title = Tin-mesoporphyrin, a potent hemeoxygenase inhibitor, for treatment of intracerebral hemorrhage: in vivo and in vitro studies| date=2000 | pmid=10872746 | last1=Wagner | first1=K. R. | last2=Hua | first2=Y. | last3=De Courten-Myers | first3=G. M. | last4=Broderick | first4=J. P. | last5=Nishimura | first5=R. N. | last6=Lu | first6=S. Y. | last7=Dwyer | first7=B. E. | journal=Cellular and Molecular Biology (Noisy-Le-Grand, France) | volume=46 | issue=3 | pages=597–608 }}