Mangafodipir
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Basic Info
| Common Name | Mangafodipir(F04096) |
| 2D Structure | |
| Description | Mangafodipir is a contrast agent delivered intravenously to enhance contrast in magnetic resonance imaging (MRI) of the liver. It has two parts, paramagnetic manganese (II) ions and the chelating agent fodipir (dipyridoxyl diphosphate, DPDP). Normal liver tissue absorbs the manganese more than abnormal or cancerous tissue. The manganese shortens the longitudinal relaxation time (called T1), making the normal tissue appear brighter in MRIs. This enhanced contrast allows lesions to be more easily identified. Acute toxicity studies in mice, rats and dogs using IV administration showed mangafodipir to have low to moderate toxicity. Repeat dose toxicity studies were conducted in rats, cynomologous monkeys and dogs. The liver and to a lesser extent the kidney were target organs of toxicity. |
| FRCD ID | F04096 |
| CAS Number | 140678-14-4 |
| PubChem CID | 160036 |
| Formula | C22H27MnN4Na3O14P2 |
| IUPAC Name | trisodium;2-[2-[carboxylatomethyl-[[2-methyl-3-oxido-5-(phosphonatooxymethyl)pyridin-4-yl]methyl]amino]ethyl-[[2-methyl-3-oxido-5-(phosphonatooxymethyl)pyridin-4-yl]methyl]amino]acetate;hydron;manganese(2+) |
| InChI Key | BENFPBJLMUIGGD-UHFFFAOYSA-I |
| InChI | InChI=1S/C22H32N4O14P2.Mn.3Na/c1-13-21(31)17(15(5-23-13)11-39-41(33,34)35)7-25(9-19(27)28)3-4-26(10-20(29)30)8-18-16(12-40-42(36,37)38)6-24-14(2)22(18)32;;;;/h5-6,31-32H,3-4,7-12H2,1-2H3,(H,27,28)(H,29,30)(H2,33,34,35)(H2,36,37,38);;;;/q;+2;3*+1/p-5 |
| Canonical SMILES | [H+].[H+].[H+].CC1=NC=C(C(=C1[O-])CN(CCN(CC2=C(C(=NC=C2COP(=O)([O-])[O-])C)[O-])CC(=O)[O-])CC(=O)[O-])COP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Mn+2] |
| Isomeric SMILES | [H+].[H+].[H+].CC1=NC=C(C(=C1[O-])CN(CCN(CC2=C(C(=NC=C2COP(=O)([O-])[O-])C)[O-])CC(=O)[O-])CC(=O)[O-])COP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Mn+2] |
| Synonyms |
Mangafodipir trisodium
Trisodium trihydrogen (OC-6-13)-((N,N'-1,2-ethanediylbis(N-((3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-4-pyridinyl)methyl)glycinato))(8-)manganate(6-)
Teslascan
Win 59010
140678-14-4
Mangafodipir Trisodium [USAN]
Teslascan (TN)
AC1L4MXZ
Manganate(6-), ((N,N'-1,2-ethanediylbis(N-((3-hydroxy-2-methyl-5-((phosphonooxy)-methyl)-4-pyridinyl)methyl)glycinato)) (8-))-, trisodium trihydrogen, (OC-6-13)-
Trisodium trihydrogen (OC-6-13)-((N,N'-ethylenebis(N-((3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridyl)methyl)glycine) 5,5'-bis(phosphato))(8-))manganate(6-)
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyridoxamines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridoxamine 5'-phosphates |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyridoxamine 5'-phosphate - Alpha-amino acid - Alpha-amino acid or derivatives - Pyridinolate - Aralkylamine - Methylpyridine - Phosphoric acid ester - Alkyl phosphate - Organic phosphoric acid derivative - Dicarboxylic acid or derivatives - Heteroaromatic compound - Amino acid or derivatives - Tertiary amine - Tertiary aliphatic amine - Carboxylic acid salt - Amino acid - Azacycle - Organic alkali metal salt - Organic transition metal salt - Carboxylic acid - Carboxylic acid derivative - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic zwitterion - Organic salt - Organic sodium salt - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Amine - Organic oxygen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 757.327 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 18 |
| Rotatable Bond Count | 13 |
| Complexity | 873 |
| Monoisotopic Mass | 757.007 |
| Exact Mass | 757.007 |
| Formal Charge | 0 |
| Heavy Atom Count | 46 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 8 |
Targets
- General Function:
- Translation repressor activity
- Specific Function:
- RNA-binding protein that binds to iron-responsive elements (IRES), which are stem-loop structures found in the 5'-UTR of ferritin, and delta aminolevulinic acid synthase mRNAs, and in the 3'-UTR of transferrin receptor mRNA. Binding to the IRE element in ferritin results in the repression of its mRNA translation. Binding of the protein to the transferrin receptor mRNA inhibits the degradation of this otherwise rapidly degraded mRNA.
- Gene Name:
- IREB2
- Uniprot ID:
- P48200
- Molecular Weight:
- 105043.65 Da
- Mechanism of Action:
- Manganese alters cellular iron homeostasis by stabilizing iron regulatory protein 2. This may occur by manganese competing directly for an iron-binding site on the iron binding protein, disrupting the cellular mechanisms responsible for its iron-dependent degradation.
References
- Crooks DR, Ghosh MC, Braun-Sommargren M, Rouault TA, Smith DR: Manganese targets m-aconitase and activates iron regulatory protein 2 in AF5 GABAergic cells. J Neurosci Res. 2007 Jun;85(8):1797-809. [17469137 ]
- General Function:
- Tubulin binding
- Specific Function:
- Its primary physiological function is unclear. Has cytoprotective activity against internal or environmental stresses. May play a role in neuronal development and synaptic plasticity. May be required for neuronal myelin sheath maintenance. May play a role in iron uptake and iron homeostasis. Soluble oligomers are toxic to cultured neuroblastoma cells and induce apoptosis (in vitro) (PubMed:12732622, PubMed:19936054, PubMed:20564047). Association with GPC1 (via its heparan sulfate chains) targets PRNP to lipid rafts. Also provides Cu(2+) or ZN(2+) for the ascorbate-mediated GPC1 deaminase degradation of its heparan sulfate side chains (By similarity).
- Gene Name:
- PRNP
- Uniprot ID:
- P04156
- Molecular Weight:
- 27661.21 Da
- Mechanism of Action:
- Manganese binds to the prion protein, altering its conformation, displacing copper, and altering the redox chemistry of the metal-protein complex. These changes are similar to those associated with prion disease.
References
- Brazier MW, Davies P, Player E, Marken F, Viles JH, Brown DR: Manganese binding to the prion protein. J Biol Chem. 2008 May 9;283(19):12831-9. doi: 10.1074/jbc.M709820200. Epub 2008 Mar 10. [18332141 ]
- Gene Name:
- PRNT
- Uniprot ID:
- Q86SH4
- Molecular Weight:
- 10755.655 Da
- Mechanism of Action:
- Manganese binds to the prion protein, altering its conformation, displacing copper, and altering the redox chemistry of the metal-protein complex. These changes are similar to those associated with prion disease.
References
- Brazier MW, Davies P, Player E, Marken F, Viles JH, Brown DR: Manganese binding to the prion protein. J Biol Chem. 2008 May 9;283(19):12831-9. doi: 10.1074/jbc.M709820200. Epub 2008 Mar 10. [18332141 ]
- General Function:
- Iron ion binding
- Specific Function:
- Catalyzes the isomerization of citrate to isocitrate via cis-aconitate.
- Gene Name:
- ACO2
- Uniprot ID:
- Q99798
- Molecular Weight:
- 85424.745 Da
- Mechanism of Action:
- Manganese interferes with amino acid metabolism by inhibiting aconitase, resulting in an increase in citrate levels. It is also believed that this direct disruption of the catalytic [4Fe-4S] cluster of aconitase by manganese produces iron regulary protein 1, resulting in alterations in cellular iron homeostasis.
References
- Crooks DR, Ghosh MC, Braun-Sommargren M, Rouault TA, Smith DR: Manganese targets m-aconitase and activates iron regulatory protein 2 in AF5 GABAergic cells. J Neurosci Res. 2007 Jun;85(8):1797-809. [17469137 ]
- General Function:
- Rna binding
- Specific Function:
- Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding.Catalyzes the isomerization of citrate to isocitrate via cis-aconitate.
- Gene Name:
- ACO1
- Uniprot ID:
- P21399
- Molecular Weight:
- 98398.14 Da
- Mechanism of Action:
- Manganese interferes with amino acid metabolism by inhibiting aconitase, resulting in an increase in citrate levels. It is also believed that this direct disruption of the catalytic [4Fe-4S] cluster of aconitase by manganese produces iron regulary protein 1, resulting in alterations in cellular iron homeostasis.
References
- Crooks DR, Ghosh MC, Braun-Sommargren M, Rouault TA, Smith DR: Manganese targets m-aconitase and activates iron regulatory protein 2 in AF5 GABAergic cells. J Neurosci Res. 2007 Jun;85(8):1797-809. [17469137 ]