2-Amino-6-mercaptopurine-9-D-riboside Hydrate

• CAS: 345909-25-3
• Catalog Number: ACM345909253
• Category: Main Products
• Molecular Weight: 299.29
• Molecular Formula: C10H13N5O4S·xH₂O
• Synonyms: 2-Amino-9-β-D-ribofuranosyl-9H-purine-6-thiol; Thioguanosine; NSC-29422
• Melting Point: 202-205 °C
• Appearance: Pale yellow to greenish grey solid

Case Study

2-Amino-6-mercaptopurine-9-D-riboside Hydrate as a Calibration Standard for Quantification of Thiopurine Nucleotides in Erythrocytes

Bajaj, Amol O., et al. Frontiers in pharmacology 13 (2022): 836812.

2-Amino-6-mercaptopurine-9-D-riboside hydrate (6-TGRib) is a stable ribose conjugate of 6-thioguanine. It serves as a key calibrator for the accurate LC-MS/MS quantification of the active cytotoxic metabolite 6-thioguanine nucleotide (6-TGN) in red blood cells (RBCs), enabling therapeutic drug monitoring of thiopurine drugs such as azathioprine and 6-mercaptopurine.
Analytical Protocol: RBCs were isolated from EDTA-anticoagulated whole blood using an automated cell washer. After lysis and protein precipitation, samples were hydrolysed at 100 °C for 2 h to convert 6-TGN to free 6-thioguanine (6-TG) and 6-methylmercaptopurine nucleotides to 6-methylmercaptopurine imidazole (6-MMP*). 6-TGRib (along with a stable isotope-labelled internal standard) was used to prepare calibration standards in thiopurine-negative RBC lysates at concentrations of 20-750 pmol/100 μL. LC-MS/MS analysis was performed on a C18 column with positive-ion electrospray.
Performance Evaluation: The method showed excellent linearity (R² = 0.996 for 6-TG) and precision (CV ≤ 3% at all concentrations). The limit of quantitation for 6-TG was 20 pmol/100 μL RBC lysate. Use of 6-TGRib as a surrogate calibrator allowed controlled assessment of hydrolysis efficiency and method accuracy. Comparison with three external laboratories showed good agreement (bias 4.6-19.2% for 6-TG). Retrospective patient data (n = 611) revealed that 81.3% of samples had subtherapeutic 6-TG concentrations, highlighting the clinical need for routine monitoring.

Custom Q&A

What is the molecular formula of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The molecular formula of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate is C10H13N5O4S.

What are the synonyms for 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The synonyms for 2-Amino-6-mercaptopurine-9-D-riboside Hydrate are 6-Thioguanosine, THIOGUANOSINE, Guanosine, 6-thio-, and NSC-29422.

What is the molecular weight of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The molecular weight of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate is 299.31 g/mol.

When was 2-Amino-6-mercaptopurine-9-D-riboside Hydrate created and last modified?

2-Amino-6-mercaptopurine-9-D-riboside Hydrate was created on July 19, 2005, and last modified on October 21, 2023.

What is the IUPAC name of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The IUPAC name of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate is 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione.

What is the InChI of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The InChI of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate is InChI=1S/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1.

What is the InChIKey of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The InChIKey of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate is OTDJAMXESTUWLO-UUOKFMHZSA-N.

What are the CAS numbers associated with 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The CAS number associated with 2-Amino-6-mercaptopurine-9-D-riboside Hydrate is 85-31-4.

What is the XLogP3 value of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate?

The XLogP3 value of 2-Amino-6-mercaptopurine-9-D-riboside Hydrate is -1.2.