≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
MT-DADMe-ImmA is an inhibitor of human 5'-methylthioadenosine phosphorylase ( MTAP ) with a K i of 90 pM.
In Vitro
Treatment of cultured cells with MT-DADMe-ImmA and MTA inhibit MTAP, increase cellular MTA concentrations, decrease polyamines, and induce apoptosis in FaDu and Cal27, two head and neck squamous cell carcinoma cell lines. The same treatment does not induce apoptosis in normal human fibroblast cell lines (CRL2522 and GM02037) or in MCF7, a breast cancer cell line with an MTAP gene deletion. MT-DADMe-ImmA alone does not induce apoptosis in any cell line, implicating MTA as the active agent. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
The t 1/2 for onset of inhibition is 50 min with complete inhibition by 250 min. MTAP activity slowly returns, giving a biological half-life for the action of oral MT-DADMe-ImmA of 6.3 days. The time-dependent growth of FaDu tumors in immunodeficient mice is suppressed by oral or intraperitoneal treatment with MT-DADMe-ImmA. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Cell Assay
Cell viability is evaluated using the Alamar Blue assay. Cells are seeded onto 96-well plates at a density of 104 cells/well and incubated with increasing concentrations of MT-DADMe-ImmA (100 pM to 100 μM) for 4 days at fixed MTA concentrations (0, 5, 10, and 20 μM). IC 50 is determined with the assay data. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:Ki: 90 pM (MTAP)
| Canonical Smiles | CSCC1CN(CC1O)CC2=CNC3=C2N=CN=C3N |
|---|---|
| IUPAC Name | (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-(methylsulfanylmethyl)pyrrolidin-3-ol |
| InChIKey | NTHMDFGHOCNNOE-ZJUUUORDSA-N |
| INCHI | 1S/C13H19N5OS/c1-20-6-9-4-18(5-10(9)19)3-8-2-15-12-11(8)16-7-17-13(12)14/h2,7,9-10,15,19H,3-6H2,1H3,(H2,14,16,17)/t9-,10+/m1/s1 |
| Isomeric SMILES | CSC[C@H]1CN(C[C@@H]1O)CC2=CNC3=C2N=CN=C3N |
| PubChem CID | 656970 |
| Molecular Weight | 293.39 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Pyrrolopyrimidines |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyrrolopyrimidines |
| Alternative Parents | Aralkylamines Aminopyrimidines and derivatives Substituted pyrroles N-alkylpyrrolidines Imidolactams Heteroaromatic compounds Trialkylamines Secondary alcohols 1,2-aminoalcohols Sulfenyl compounds Dialkylthioethers Azacyclic compounds Primary amines Organopnictogen compounds Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Pyrrolopyrimidine - Aminopyrimidine - Aralkylamine - Pyrimidine - Substituted pyrrole - N-alkylpyrrolidine - Imidolactam - Heteroaromatic compound - Pyrrole - Pyrrolidine - 1,2-aminoalcohol - Tertiary aliphatic amine - Secondary alcohol - Tertiary amine - Azacycle - Dialkylthioether - Sulfenyl compound - Thioether - Amine - Organic nitrogen compound - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Organopnictogen compound - Alcohol - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
| External Descriptors | Not available |
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| Solubility | DMSO : 100 mg/mL (340.84 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 293.390 g/mol |
| XLogP3 | 0.000 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Exact Mass | 293.131 Da |
| Monoisotopic Mass | 293.131 Da |
| Topological Polar Surface Area | 116.000 Ų |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Complexity | 334.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
