154-42-7 6-Thioguanine AKSci J10163
 
 
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  J10163    AKSci Reference Standard
6-Thioguanine, 99% (HPLC)
 
2-Amino-6-mercaptopurine
6-Mercaptoguanine
Tioguanine
more..
IDENTITY
CAS Number:154-42-7
MDL Number:MFCD00233553
MF:C5H5N5S
MW:167.19
EINECS:205-827-2
BRN:157765
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:99% (HPLC)
Physical Form (at 20°C):Solid
Melting Point:360°C
Long-Term Storage:Store long-term in a cool, dry place
DOT/IATA TRANSPORT INFORMATION
UN #:UN2811
Hazard Class:6.1; Poison
Packing Group:III
A hazmat fee may apply, depending on the amount ordered.

BIOLOGICAL INFO
Solubility:50mg/1ml in 10% NaOH; clear light green solution
Form:Free base
Research Area:Cancer

REVIEW
 Thioguanine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to 6-thioguanilyic acid (TGMP), which reaches high intracellular concentrations at therapeutic doses. TGMP interferes with the synthesis of guanine nucleotides by its inhibition of purine biosynthesis by pseudofeedback inhibition of glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway of purine ribonucleotide synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. Thioguanine nucleotides are incorporated into both the DNA and the RNA by phosphodiester linkages, and some studies have shown that incorporation of such false bases contributes to the cytotoxicity of thioguanine. Its tumor inhibitory properties may be due to one or more of its effects on feedback inhibition of de novo purine synthesis; inhibition of purine nucleotide interconversions; or incorporation into the DNA and RNA. The overall result of its action is a sequential blockade of the utilization and synthesis of the purine nucleotides.

REFERENCES
[1]Vora A, Mitchell CD, Lennard L, et al. (October 2006). Toxicity and efficacy of 6-thioguanine versus 6-mercaptopurine in childhood lymphoblastic leukaemia: a randomised trial. Lancet 368 (9544): 1339-48. doi:10.1016/S0140-6736(06)69558-5. PMID 17046466.
[2] Evans WE. (2004). Pharmacogenetics of thiopurine S-methyltransferase and thiopurine therapy.. Ther Drug Monit. 26 (2): 186-91. PMID 12891528.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Danger

Hazard Statements
H301

Precautionary Statements
P264; P270; P301+P310; P321; P330; P405; P501

Current as of June 30, 2022

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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For research use only. Not for diagnostic or therapeutic use. Not for human use. AK Scientific, Inc. does not sell to individuals. If you are a first-time customer, please email for review at least two official business documents issued by your local jurisdiction, state/province, or country.

WARNING: Attention California residents: This product can expose you to chemicals including 6-Thioguanine, which is known to the State of California to cause birth defects or other reproductive harm. For more information, go to www.P65Warnings.ca.gov.


CATEGORIES
 Heterocyclic Building Blocks > Purines, Amines, Thiols
 Nucleobases > Purines
 Nucleobases > Purines


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