2-amino-6,7-dihydro-1H-purine-6-thione

• ChemBase ID: 102918
• Molecular Formular: C5H5N5S
• Molecular Mass: 167.1917
• Monoisotopic Mass: 167.02656619
• SMILES: Nc1nc2c([nH]cn2)c(=S)[nH]1
• Canonical SMILES: Nc1nc2nc[nH]c2c(=S)[nH]1
• InChI: InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
• InChIKey: WYWHKKSPHMUBEB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-6,7-dihydro-1H-purine-6-thione
• IUPAC Traditional name: 2-aminopurine-6(1h)-thione
• Synonyms: 6-Thioguanine; 2-Amino-6-purinethiol; 2-AMINO-6-MERCAPTOPURINE; 6-Thioguanine; 2-Amino-6-mercaptopurine; 2-amino-1,7-dihydro-6H-purine-6-thione; 2-氨基-6-巯嘌呤; 2-氨基-6巯基嘌呤; 6-硫鸟嘌呤

Database IDs

• CAS Number: 154-42-7
• EC Number: 205-827-2
• MDL Number: MFCD00005568; MFCD00233553
• Beilstein Number: 157765
• PubChem SID: 162090773; 24890748; 24890892
• PubChem CID: 2723601

CALCULATED PROPERTIES

• Acid pKa: 9.962727
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.22414501
• LogD (pH = 7.4): -0.21823545
• Log P: -0.21708015
• Molar Refractivity: 47.3254 cm^3
• Polarizability: 16.347652 Å^3
• Polar Surface Area: 79.09 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: lyophilized powder
• Melting Point: ≥300 °C(lit.); 359 - 360°C
• Hydrophobicity(logP): -1.882

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: UP0740000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25; R:22-36/37/38-47
• Safety Statements: 28-36/37/39-45; S:20-26-37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ~98%; ≥96% (HPLC); ≥98%; 95%
• Concentration: 50 ×
• Grade: Hybri-Max™; purum
• Suitability: suitable for hybridoma
• Impurities: ≤3% guanine; endotoxin, tested
• Sterility: γ-irradiated
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C5H5N5S

DETAILS

MP Biomedicals - 02105542

Crystalline
Purity: Approx. 98%
Antineoplastic

Sigma Aldrich - A4660

Application
Used in hybridoma formation applications as a selection agent.
Reconstitution
Reconstitute contents of vial with 10 ml sterile cell culture medium. Stock solution is sufficient to prepare 500 ml medium. Final working concentration: 30 μM 2-amino-6-mercaptopurine.
Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1
Legal Information
Hybri-Max is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - A4882

Biochem/physiol Actions
Antimetabolite used in the treatment of leukemias. Competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase, which catalzyes a critical step in the generation of purine nucleotides.
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1
包装
1, 5 g in glass bottle
100, 250, 500 mg in glass bottle

Sigma Aldrich - A76907

Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1

Sigma Aldrich - 88800

Other Notes
Antineoplastic agent2; substrate for HGPRTase, converted to 6-thio-GMP, which then inhibits vital metabolic sequences in myelocytic and acute lymphocytic leukemia.1
Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.1