A4882
6-Thioguanine
≥98%, Guanine antimetabolite, powder
동의어(들):
2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
로그인조직 및 계약 가격 보기
크기 선택
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C5H5N5S
CAS 번호:
Molecular Weight:
167.19
Beilstein:
157765
EC Number:
MDL number:
UNSPSC 코드:
12352202
PubChem Substance ID:
NACRES:
NA.77
제품 이름
6-Thioguanine, ≥98%
생물학적 소스
synthetic (organic)
Quality Level
분석
≥98%
양식
powder
mp
≥300 °C (lit.)
solubility
1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow
저장 온도
room temp
SMILES string
NC1=Nc2nc[nH]c2C(=S)N1
InChI
1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI key
WYWHKKSPHMUBEB-UHFFFAOYSA-N
유전자 정보
human ... IMPDH1(3614), IMPDH2(3615)
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일반 설명
6-Thioguanine is a variant of guanine with hydrogen bonding at the N-7 of the purine ring. Its association with cytosine alters the dimension of the base stacking. 6-Thioguanine usage in treating inflammatory bowel disease (IBD) contributes to nodular regenerative hyperplasia (NRH) in the liver.
애플리케이션
6-Thioguanine has been used:
- to induce autophagy and apoptosis in colorectal cancer cell lines HCT116
- as a selection marker in the mutation and survival assay in chinese hamster lung fibroblasts culture V79
- as a selection marker in clonogenic Lung metastasis assay of 4T1-luc cells
생화학적/생리학적 작용
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.
신호어
Danger
유해 및 위험 성명서
예방조치 성명서
Hazard Classifications
Acute Tox. 3 Oral
Storage Class Code
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
개인 보호 장비
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Interconnections between apoptotic and autophagic pathways during thiopurine-induced toxicity in cancer cells: the role of reactive oxygen species
Chaabane W and Appell ML
Testing, 7(46), 75616-75616 (2016)
Tumor-suppressor inactivation of GDF11 occurs by precursor sequestration in triple-negative breast cancer
Bajikar SS, et al.
Developmental Cell, 43(4), 418-435 (2017)
6-thioguanine can cause serious liver injury in inflammatory bowel disease patients
Dubinsky MC, et al.
Gastroenterology, 125(2), 298-303 (2003)
Crystal and molecular structure of 6-thioguanine
Bugg CE and Thewalt U
Journal of the American Chemical Society, 92(25), 7441-7445 (1970)
Delayed effects of accelerated heavy ions on the induction of HPRT mutations in V79 hamster cells
Blaha P, et al.
Mutation Research. Fundamental and Molecular Mechanisms of Mutagenesis, 803(46), 35-41 (2017)
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