6-Thioguanine

Modify Date: 2024-01-04 15:06:53

6-Thioguanine structure	Common Name	6-Thioguanine
	CAS Number	154-42-7	Molecular Weight	167.192
	Density	2.1±0.1 g/cm3	Boiling Point	460.7±37.0 °C at 760 mmHg
	Molecular Formula	C₅H₅N₅S	Melting Point	≥300 °C(lit.)
	MSDS	Chinese USA	Flash Point	232.4±26.5 °C
	Symbol	GHS06	Signal Word	Danger

Use of 6-Thioguanine

6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively.

Name	tioguanine
Synonym	More Synonyms

Description	6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Deubiquitinase Signaling Pathways >> Anti-infection >> SARS-CoV Research Areas >> Inflammation/Immunology Research Areas >> Cancer Research Areas >> Infection
Target	IC50: 25 μM (PLpros), 40 μM (Recombinant human USP2)[3]
In Vitro	6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively[1]. 6-Thioguanine affects the methylation of cytosine residues by purified DNA methyltransferases including human DNMT1 and bacterial HpaII methylase. 6-Thioguanine (1 or 3 μM) decreases global cytosine methylation in Jurkat T cells and cytosine methylation in human cells at 3 μM[2]. 6-Thioguanine (18.75, 37.50, or 75.00 μM) adversely affects cell viability, but with no effect on LDH or ALT activity[3].
Cell Assay	Treatments consists of 3 thiopurines (azathioprine, 6-mercaptopurine, and 6-thioguanine) at each of 6 concentrations (0.468, 0.937, 1.875, 3.750, 7.500, and 15.000 μM). Each thiopurinee is dissolved in DMSO solution to achieve a concentration of 10 mg/mL. Sterile filtered maintenance medium is used to further dilute each thiopurine solution to each of the 6 treatment concentrations. Twenty-four hours after the hepatocytes are plated on 96-well culture[3].
References	[1]. Chuang SJ, et al. 6-Thioguanine is a noncompetitive and slow binding inhibitor of human deubiquitinating protease USP2. Sci Rep. 2018 Feb 15;8(1):3102. [2]. Wang H, et al. 6-Thioguanine perturbs cytosine methylation at the CpG dinucleotide site by DNA methyltransferases in vitro and acts as a DNA demethylating agent in vivo. Biochemistry. 2009 Mar 17;48(10):2290-9. [3]. LaDuke KE, et al. Effects of azathioprine, 6-mercaptopurine, and 6-thioguanine on canine primary hepatocytes. Am J Vet Res. 2015 Jul;76(7):649-55.

Density	2.1±0.1 g/cm3
Boiling Point	460.7±37.0 °C at 760 mmHg
Melting Point	≥300 °C(lit.)
Molecular Formula	C₅H₅N₅S
Molecular Weight	167.192
Flash Point	232.4±26.5 °C
Exact Mass	167.026566
PSA	119.28000
LogP	-0.99
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	2.071
Water Solubility	soluble

6-Thioguanine MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP0740000

CHEMICAL NAME :: Purine-6(1H)-thione, 2-amino-

CAS REGISTRY NUMBER :: 154-42-7

LAST UPDATED :: 199807

DATA ITEMS CITED :: 32

MOLECULAR FORMULA :: C5-H5-N5-S

MOLECULAR WEIGHT :: 167.21

WISWESSER LINE NOTATION :: T56 BNM FYM INJ FUS HZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Human

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 160 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - hemorrhage Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 54 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - hemorrhage Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LD10 - Lethal Dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1600 mg/kg

TOXIC EFFECTS :: Blood - changes in bone marrow (not otherwise specified)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 23720 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - conjunctive irritation Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 55990 ug/kg/5D-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 56 mg/kg/2W-I

TOXIC EFFECTS :: Blood - normocytic anemia Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 650 mg/kg/26W-I

TOXIC EFFECTS :: Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 46500 ug/kg/5D-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 19950 ug/kg/4D-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 23700 ug/kg/13D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from large intestine Nutritional and Gross Metabolic - body temperature increase Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 5700 ug/kg/13D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from large intestine Nutritional and Gross Metabolic - body temperature increase Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 25 mg/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 10 mg/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 15 ug/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 139,149,1984 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5676 No. of Facilities: 18 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 82 (estimated) No. of Female Employees: 27 (estimated)

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T:Toxic;
Risk Phrases	R25
Safety Phrases	S28-S36/37/39-S45-S28A
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	UP0740000
Packaging Group	III
Hazard Class	6.1
HS Code	2933990090

Guanine

CAS#:73-40-5

~78%

6-Thioguanine

CAS#:154-42-7

Literature: Tomsons, U. A.; Avots, A. A.; Kolesnikova, I. A. Pharmaceutical Chemistry Journal, 1985 , vol. 19, # 2 p. 136 - 138 Khimiko-Farmatsevticheskii Zhurnal, 1985 , vol. 19, # 2 p. 206 - 209

N,9-Diacetylguanine

CAS#:3056-33-5

6-Thioguanine

CAS#:154-42-7

Literature: Pharmaceutical Chemistry Journal, , vol. 19, # 2 p. 136 - 138 Khimiko-Farmatsevticheskii Zhurnal, , vol. 19, # 2 p. 206 - 209

Precursor 2
CAS#:73-40-5 Guanine CAS#:3056-33-5 N,9-Diacetylguanine
DownStream 4
CAS#:5581-52-2 guaneran CAS#:452-06-2 2-Aminopurine CAS#:89853-37-2 2-[(2-amino-5H-... CAS#:42204-31-9 Acetic acid,2-[...

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

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Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

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Drug-induced liver injury is a major issue of concern and has led to the withdrawal of a significant number of marketed drugs. An understanding of structure-activity relationships (SARs) of chemicals ...

MFCD00233553

2-Amino-6-methoxy purine

tabloid

2-aminomercaptopurine

2-amino-9H-purine-6(1H)-thione

tioguanin

2-Amino-6-purinethiol

bw5071

Tioguanine

2-Amino-6-mercaptopurine,2-Amino-6-purinethiol

7H-Purine-6-thiol, 2-amino-

2-Amino-6-mercaptopurine

2-Amino-1H-purine-6(7H)-thione

6-Thioguanine

lanvis

6-tg

thioguanine

thio-guanin

6-thioguanidine

EINECS 205-827-2

wellcomeu3b

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

6-Mercaptoguanine

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: 6-Thioguanine
Price: ￥248.0/1g ￥778.0/5g
Purity: 98.0%
Stocking Period: Inquiry
Contact: Liu jia

DC Chemicals Limited
China
Product Name: 6-TG/Thioguanine
Price: $300.0/1g
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Zhejiang Hangyu API Co., Ltd
China
Product Name: 6-Thioguanine
Price: ￥Inquiry/1kg
Purity: 99.5%
Stocking Period: Inquiry
Contact: Vinnie

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Price: $66/10mM*1mLinDMSO

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6-Thioguanine

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