6-Mercaptopurine (6-MP) Monohydrate

Alias: 6-MP; Mercaptopurine; NSC 755; 6 MP; NSC755; 6MP; NSC-755; 6-Mercaptopurine hydrate
Cat No.:V1428 Purity: ≥98%
6-Mercaptopurine monohydrate (6-MP; NSC 755; 6 MP; NSC755; 6MP; NSC-755; Purinethol), the hydrated form of 6-Mercaptopurine, is an approved anticancer and immunosuppressive drug used for the treatment of ALL-acute lymphocytic leukemia, CML-chronic myeloid leukemia, Crohns disease, and ulcerative colitis.
6-Mercaptopurine (6-MP) Monohydrate Chemical Structure CAS No.: 6112-76-1
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
2g
5g
10g
50g
Other Sizes

Other Forms of 6-Mercaptopurine (6-MP) Monohydrate:

  • Mercaptopurine (6-MP)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

6-Mercaptopurine monohydrate (6-MP; NSC 755; 6 MP; NSC755; 6MP; NSC-755; Purinethol), the hydrated form of 6-Mercaptopurine, is an approved anticancer and immunosuppressive drug used for the treatment of ALL-acute lymphocytic leukemia, CML-chronic myeloid leukemia, Crohn's disease, and ulcerative colitis. Thiopurine methyltransferase metabolites are incorporated into DNA and RNA, inhibiting de novo purine synthesis.

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). A dose-dependent increase in NR4A3 protein levels is observed with 6-Mercaptopurine hydrate. Insulin-stimulated cells’ cell surface GLUT4 increases 2.9–4.4 fold (P<0.01) and basal cells’ cell surface GLUT4 increases 1.8–3.6 fold (P<0.01) over controls after 6-MP treatment. Furthermore, under both basal and insulin-stimulated conditions, 6-Mercaptopurine hydrate is found to significantly and dose-responsively increase phospho-AS160[2].

ln Vivo
After receiving 6-Mercaptopurine hydrate (6-MP) treatment, the S phase cell population in the fetal telencephalons of that group increases at 36 and 48 hours and reaches the control level at 72 hours. The G2/M phase cell population increases over the course of 24 hours, peaks at 36 hours, declines at 48 hours, and then returns to the control level at 72 hours. In contrast, the sub-G1 phase cell population, also known as apoptotic cells, starts to grow at 36 h, peaks at 48 h, and then starts to decline at 72 h[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
C5H6N4OS
Molecular Weight
170.19
Exact Mass
170.03
Elemental Analysis
C, 35.29; H, 3.55; N, 32.92; O, 9.40; S, 18.84
CAS #
6112-76-1
Related CAS #
50-44-2
Appearance
Solid powder
SMILES
C1=NC2=C(N1)C(=S)N=CN2.O
InChi Key
WFFQYWAAEWLHJC-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H4N4S.H2O/c10-5-3-4(7-1-6-3)8-2-9-5;/h1-2H,(H2,6,7,8,9,10);1H2
Chemical Name
3,7-dihydropurine-6-thione;hydrate
Synonyms
6-MP; Mercaptopurine; NSC 755; 6 MP; NSC755; 6MP; NSC-755; 6-Mercaptopurine hydrate
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: 35.7~100 mg/mL (234.7~587.6 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.8758 mL 29.3789 mL 58.7579 mL
5 mM 1.1752 mL 5.8758 mL 11.7516 mL
10 mM 0.5876 mL 2.9379 mL 5.8758 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

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.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05506332 Recruiting Drug: 6-mercaptopurine
Drug: Venetoclax
Acute Myeloid Leukemia,
in Relapse
Acute Myeloid Leukemia
Refractory
University Hospital, Antwerp July 15, 2022 Phase 1
NCT05276284 Recruiting Combination Product: Atezolizumab,
6-mercaptopurine, 6-thioguanine
Solid Tumor, Adult
Metastatic Cancer
Kristoffer Rohrberg September 1, 2022 Phase 1
Phase 2
NCT01432145 Completed Drug: 6-Mercaptopurine
Drug: Methotrexate
Breast Cancer
Ovarian Cancer
University of Oxford May 2011 Phase 2
NCT01324336 Completed Drug: 6-Mercaptopurine Acute Lymphoblastic Leukemia Children's Mercy Hospital Kansas
City
July 2011 N/A
NCT00548431 Completed Drug: 6-mercaptopurine Leukemia, Lymphocytic, Acute Rigshospitalet, Denmark December 2007 Phase 2
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 knockdown 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 6-MP treatment on the protein expression of glucose transporters GLUT1 and GLUT4 and GLUT4 translocation to the cell surface. Am J Physiol Endocrinol Metab . 2013 Nov 1;305(9):E1081-92.
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