Mercaptopurine (6-MP)

Alias: 6-MP; 6-Thiohypoxanthine; 6-thiopurine; 6-mercaptopurine
Cat No.:V1452 Purity: ≥98%
Mercaptopurine(also called 6-MP; 6-Thiohypoxanthine; 6-thiopurine;6-mercaptopurine; Purinethol) is an approved anticancer medication usedto treat malignancies.
Mercaptopurine (6-MP) Chemical Structure CAS No.: 50-44-2
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Mercaptopurine (also called 6-MP; 6-Thiohypoxanthine; 6-thiopurine; 6-mercaptopurine; Purinethol) is an approved anticancer medication used to treat malignancies. Furthermore, it is a commonly used immunosuppressive medication for the treatment of autoimmune disorders like rheumatoid arthritis, dermatological issues, inflammatory bowel disease, and rejection of solid organ transplants. By integrating thiopurine methyltransferase metabolites into DNA and RNA, it prevents the synthesis of purines from scratch.

Biological Activity I Assay Protocols (From Reference)
Targets
endogenous purines
ln Vitro

6-Mercaptopurine hydrate (6-MP) dose-responsively increases NR4A3 transcriptional activity by 1.6–11 fold (P<0.01). It is discovered that 6-Mercaptopurine hydrate raises NR4A3 protein levels in a dose-dependent manner. Cell surface GLUT4 is increased by 6-MP treatment 1.8–3.6 times (P<0.01) in basal cells and 2.9–4.4 times (P<0.01) in insulin-stimulated cells compared to controls. It is also discovered that, in both basal and insulin-stimulated conditions, 6-Mercaptopurine hydrate significantly and dose-responsively increases phospho-AS160[2].

ln Vivo
At 36 and 48 hours after treatment, the S phase cell population in the fetal telencephalons of the 6-Mercaptopurine hydrate (6-MP) group increases, and at 72 hours, it returns to the control level. After starting to rise at 24 hours, reaching its peak at 36 hours, declining at 48 hours, and ultimately stabilizing at 72 hours, the G2/M phase cell population gradually diminishes. Conversely, the cell population in the sub-G1 phase, or apoptotic cells, starts to grow at 36 hours, peaks at 48 hours, and then starts to decline at 72 hours[3].
Enzyme Assay
L6 myotubes are incubated for 24 hours in either DMSO control or 6-Mercaptopurine hydrate (6-MP), with treatments in serum-free DMEM during the last 3 hours. They are then incubated for an additional 60 minutes at 37°C in the presence or absence of 100 nM insulin. Subsequently, 50 μg of protein lysates are gathered, put through SDS-PAGE, and then immunoblotted using primary antibodies for an entire night at 4°C. Using Image J software, densitometric analysis of scanned films is used to finally quantify the proteins[2].
Cell Assay
The Cell Viability Assay is used to quantify cell viability. 10,000 L6 skeletal muscle cells are seeded per well in 96-well plates, and after 7 days, the cells differentiate into myotubes. Before the assay, cells are treated for 24 hours with varying doses of 6-Mercaptopurine hydrate (6-MP). After 30 minutes of room temperature equilibration, 50 μL of Cell Titer-Glo reagent is added to each well, and the plates are mixed for 12 minutes on an orbital shaker to analyze the viability of the cells. A luminometer is used to measure luminosity[2].
Animal Protocol
In this study, pregnant rats that are about thirteen weeks old are employed. The animals are kept in separate wire-mesh cages in an air-conditioned room with constant temperature and humidity levels (23±3°C and 50±20%, respectively), 10 cycles of ventilation (lights on for 12 hours and dark for 12 hours), and free access to pelleted food and water. In the experiment, three dams are each sacrificed by exsanguination from the abdominal aorta under ether anesthesia at 12, 24, 36, 48, and 72 hours after fifteen pregnant rats receive an intraperitoneal injection of 50 mg/kg 6-Mercaptopurine hydrate (6-MP) on E13. Each dam's fetuses are removed via Caesarean section. Three dams are sacrificed at each of the same time points, and fifteen pregnant rats are injected intraperitoneally (i.p.) with a 2.0% methylcellulose solution in distilled water as controls at E13[3].
References

[1]. Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67.

[2]. 6-Mercaptopurine augments glucose transport activity in skeletal muscle cells in part via a mechanism dependent upon orphan nuclear receptor NR4A3. Am J Physiol Endocrinol Metab. 2013 Nov 1;305(9):E1081-92.

[3]. 6-Mercaptopurine (6-MP) induces cell cycle arrest and apoptosis of neural progenitor cells in the developing fetal rat brain. Neurotoxicol Teratol. 2009 Mar-Apr;31(2):104-9.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C5H4N4S
Molecular Weight
152.18
Exact Mass
152.02
Elemental Analysis
C, 39.46; H, 2.65; N, 36.82; S, 21.07
CAS #
50-44-2
Appearance
Solid powder
SMILES
C1=NC2=C(N1)C(=S)N=CN2
InChi Key
GLVAUDGFNGKCSF-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
Chemical Name
3,7-dihydropurine-6-thione
Synonyms
6-MP; 6-Thiohypoxanthine; 6-thiopurine; 6-mercaptopurine
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 30~35.7 mg/mL (197.1~234.7 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.5712 mL 32.8558 mL 65.7117 mL
5 mM 1.3142 mL 6.5712 mL 13.1423 mL
10 mM 0.6571 mL 3.2856 mL 6.5712 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05811845 Recruiting N/A Acute Lymphoblastic Leukemia IRCCS Burlo Garofolo July 30, 2022 N/A
NCT01503632 Active
Recruiting
Behavioral: Behavioral
Intervention
Drug: Mercaptopurine
Acute Lymphoblastic Leukemia Children's Oncology Group February 21, 2012 Phase 3
NCT02046694 Completed Drug: Allopurinol Acute Lymphoblastic Leukemia
(ALL)
Sidney Kimmel Comprehensive
Cancer Center at Johns Hopkins
January 6, 2014 Early Phase 1
NCT00648336 Completed Drug: Mercaptopurine 50 mg
Drug: Purinethol® Tablets 50 mg
Healthy Mylan Pharmaceuticals Inc November 2003 Phase 1
NCT01324336 Completed Drug: 6-Mercaptopurine Acute Lymphoblastic Leukemia Children's Mercy Hospital Kansas
City
July 2011 N/A
Biological Data
  • Effects of 6-mercaptopurine (6-MP) on glucose transport activity and cell viability in L6 myotubes. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
  • Effects of 6-MP on NR4A3 transcriptional activity and protein expression. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
  • Effects of NR4A3 overexpression and 6-MP on glucose transport in L6 skeletal muscle cells. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
  • Effects of NR4A3 knockdown and 6-MP on glucose transport in L6 skeletal muscle cells. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
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