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CAS: 154-42-7
分子式: C5H5N5S
分子量: 167.19
熔点: 360℃
中文名称: 
2-氨基-6-嘌呤硫醇
6-巯基鸟嘌呤
硫鸟嘌呤
6-硫代鸟嘌呤
2-氨基-6-巯基嘌呤
英文名称: 
Lanuis
2-amino-purine-6(1h)-thion
2-amino-1,7-dihydro-6h-purin-6-thion
2-amino-1,7-dihydro-6h-purine-6-thione
2-amino-6-mercaptopurine
2-amino-6-merkaptopurin
2-amino-6-mp
2-amino-6-purinethiol
2-aminopurin-6-thiol
2-aminopurine-6(1h)-thione
2-aminopurine-6-thiol
6-mercapto-2-aminopurine
6-mercaptoguanine
6-tg
6-thioguanine
2-amino-1,7-dihydro-6h-purine-6-thion
bw 5071
thio-guanin
lanvis
nsc-752
2-amino-purine-6-thio
purine-b-thiol, 2-amino
tabloid
tg
thg
thioguanine
tioguanin
tioguanine
wellcome u3b
展开更多英文名
性质描述: 淡黄色针状结晶。熔点>360℃。易溶于稀碱溶液,不溶于水、乙醇、氯仿。无臭、无味。
生产方法: 由鸟嘌呤经置换反应制得。将吡啶、盐酸鸟嘌呤及五硫化二磷加热回流16h后,常压回收吡啶至反应物呈粘稠状,再状压蒸馏至吡啶回收完。降温至70℃以下,缓缓加入约鸟嘌呤量20倍的水(仿止溢料),加完后继续搅拌半小时,冷却过液,过滤,水洗。将紫沉淀物投入工业氨水中,加活性炭,加热回流1h,趁热滤除活性炭,滤兴高采烈用盐酸调节pH至4,冷却结晶。过滤,再精制一次,得硫鸟嘌呤。
用途: 肮肿瘤药。对急性白血病和慢性粒细胞白血病有缓解作用。大剂量对绒癌有效有较好疗效。
推荐供应商
货号品牌产品名称规格包装、参考价格详情
T797831MACKLIN6-硫鸟嘌呤10mM in DMSO401元/1ml;   展开
储存:-20°C
T819095MACKLIN6-硫鸟嘌呤98%46元/250mg;   100元/1g;   302元/5g;   998元/25g;   3787元/100g;   展开
储存:室温
状态:白色到浅黄绿色粉末
T0212TCI6-Thioguanine>95.0%(HPLC)435元/1G;   1310元/5G;   展开

基本信息

纯度/分析方法>95.0%(HPLC)
分子式/分子量C5H5N5S = 167.19
外观与形状(20℃)固体
Reaxys-RN1074099
PubChem物质ID87576202
SDBS (AIST Spectral DB)4204
Merck Index (14)9337
MDL编号MFCD00233553

技术规格

AppearanceLight orange to Yellow to Green powder to crystal
Purity(HPLC)min. 95.0 area%

安全信息

图形或危害标志
信号词危险
危险性说明H301 : 吞咽会中毒。
H315 : 造成皮肤刺激。
H319 : 造成严重眼刺激。
防范说明P501 : 将内装物/容器送到批准的废物处理厂处理。
P270 : 使用本产品时不要进食、饮水或吸烟。
P264 : 作业后彻底清洗皮肤。
P280 : 戴防护手套/戴防护眼罩/戴防护面具。
P302 + P352 : 如皮肤沾染:用水充分清洗。
P337 + P313 : 如仍觉眼刺激:求医/就诊。
P305 + P351 + P338 : 如进入眼睛:用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出,取出隐形眼镜。继续冲洗。
P362+P364 : 脱掉沾污的衣服,清洗后方可重新使用。
P332 + P313 : 如发生皮肤刺激:求医/就诊。
P301 + P310 + P330 : 如误吞咽:立即呼叫急救中心/医生。漱口。
P405 : 存放处须加锁。

相关法规

RTECS#UP0740000

运输信息

UN编号UN2811
类别6.1
包装类别 III
监管条件代码(*)
268355J&K6-Thioguanine98%, 一种抗白血病和免疫抑制剂243元/500MG;   413元/1G;   1244元/5G;   展开

基本信息

分子式C5H5N5S
分子量167.20
熔点300
MDL编码MFCD00233553
Beilstein157765
EINECS 编号205-827-2

产品描述

Thioguanine是一种嘌呤类的抗代谢药物,抑制了DNMT1的活性,广泛用于治疗急性淋巴细胞白血病,自身免疫性疾病(如克罗恩氏病,类风湿关节炎)和器官移植接受患者。

靶点(IC50 & Targe)

DNMT1

体外研究

Thioguanine掺入改变在etoposide存在和不存在时拓扑异构酶II诱导的DNA切割。[1] Thioguanine改变双链DNA的结构和降低双链DNA的热稳定性,但在6SG可以形成存在双链DNA。[2] 在两个错配修复熟练和缺陷型HCT116和HeLa细胞中,6-Thioguanine诱导在类似的凋亡。[3]6-Thioguanine能结合到DNA,不像典型的DNA碱基,它是一种强的UVA的发色团在342纳米具有最大吸收。6-Thioguanine是光敏剂和活性氧源。[4]

体内研究

在异种移植物模型中,6-Thioguanine是和PARP抑制剂一样有效的选择性杀死BRCA2缺陷肿瘤。6-Thioguanine有效杀死BRCA1缺陷型PARP抑制剂抗性的肿瘤。6-Thioguanine可以杀死细胞,肿瘤通过BRCA2基因的遗传逆转获得了抗PARP抑制剂的抗性。[5]

参考文献

[1] Krynetskaia NF, et al. FASEB J,?000, 14(14), 2339-2344.

[2] Marathias VM, et al. Nucleic Acids Res,?999, 27(14), 2860-2867.

[3] Yamane K, et al. Clin Cancer Res,?005, 11(6), 2355-2363.

[4] Brem R, et al. Photochem Photobiol,?012, 88(1), 5-13.

[5] Issaeva N, et al. Cancer Res,?010, 70(15), 6268-6276.

安全信息

图形或危害标志
提示语Danger
危险说明H301
防范说明P301+P310
UN号码2811
危险分类6.1
包装等级III
WGK3
RTECSUP0740000
TSCA
B21280Alfa Aesar6-Thioguanine98%1586元/1g;   7039元/5g;   展开

应用
6-Thioguanine acts as an antineoplastic and purine antimetabolite. It is also useful as an inhibition of stimulated expression of TNF-related apoptosis-inducing ligand (TRAIL) protein. It is involved in the treatment of acute leukemias and Psoriasis. Further, it is used for the treatment of ulcerative colitis and autoimmune diseases.

备注
Incompatible with strong oxidizing agents.

基本信息

MDL
MFCD00233553

EINECS
205-827-2

分子式
C5H5N5S

分子量
167.19

熔点
>360°

灵敏度
Ambient temperatures.

形态
Powder

溶解性
Soluble in dilute solutions of alkali hydroxides and hot alcohol. Insoluble in water.

Beilstein
157765

Merck
14,9337

GHS危害和防范说明

GHS符号

Hazard Statements
H301
Toxic if swallowed.

Precautionary Statements
P264-P270-P301+P310a-P321-P405-P501a
Wash thoroughly after handling.Do not eat, drink or smoke when using this product.Do not eat, drink or smoke when using this product.Specific treatment (see label).Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.

安全信息

危险等级
6.1

包装组
III

危险类别
25
Toxic if swallowed.

安全等级
20-36-45-60
When using do not eat or drink.Wear suitable protective clothing.In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).This material and its container must be disposed of as hazardous waste

RTECS
UP0740000

TSCA

A4882Sigma-Aldrich6-Thioguanine≥98%610.79元/100 MG;   781.04元/250 MG;   1387.79元/500 MG;   2311.22元/1 G;   9136.19元/5 G;   展开

产品说明

一般描述

6-硫鸟嘌呤是鸟嘌呤的变体,在嘌呤环的 N-7 位有氢键。它与胞嘧啶的结合改变了碱基堆积的维度。6-硫鸟嘌呤是治疗炎症性肠病 (IBD) 的有效药物,可导致肝脏结节性再生性增生 (NRH)。

应用

6-硫鸟嘌呤已用于:

  • 诱导结直肠癌细胞系 HCT116 的自噬和凋亡
  • 在中国仓鼠肺成纤维细胞培养 V79 的突变和存活试验中作为选择标记
  • 在 4T1-luc 细胞的克隆源性肺转移试验中作为选择标记

包装

1, 5 g in glass bottle
100, 250, 500 mg in glass bottle

生化/生理作用

核糖基化并通过与天然嘌呤碱相同的途径磷酸化;作为核苷酸,抑制参与核酸合成的多种细胞过程。作为白血病的有效治疗方法已有悠久的历史。
用于治疗白血病的抗代谢药。与次黄嘌呤和鸟嘌呤竞争次黄嘌呤-鸟嘌呤磷酸核糖转移酶,后者是生成嘌呤核苷酸的关键步骤。

基本信息

经验(实验)分子式C5H5N5S
分子量167.19
Beilstein157765
EC 号205-827-2
MDL编号MFCD00233553
PubChem化学物质编号24890748
NACRESNA.77

产品性质

质量水平200
测定≥98%
形式powder
mp≥300 ℃ (lit.)
SMILES stringNC1=Nc2nc[nH]c2C(=S)N1
InChI1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI keyWYWHKKSPHMUBEB-UHFFFAOYSA-N
Gene Informationhuman ... IMPDH1(3614), IMPDH2(3615)

安全信息

象形图GHS06
警示用语:Danger
危险声明H301
预防措施声明P301 + P310
危险分类Acute Tox. 3 Oral
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
个人防护装备Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
1660000USPThioguanineUnited States Pharmacopeia (USP) Reference Standard3036.37元/200 MG;   展开

产品说明

一般描述

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

生化/生理作用

核糖基化并通过与天然嘌呤碱相同的途径磷酸化;作为核苷酸,抑制参与核酸合成的多种细胞过程。作为白血病的有效治疗方法已有悠久的历史。

分析说明

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

其他说明

USP issued SDS can be found here.
Sales restrictions may apply.

基本信息

经验(实验)分子式C5H5N5S
分子量167.19
Beilstein157765
MDL编号MFCD00233553
PubChem化学物质编号329751279
NACRESNA.24

产品性质

等级pharmaceutical primary standard
manufacturer/tradenameUSP
mp≥300 ℃ (lit.)
application(s)pharmaceutical (small molecule)
格式neat
SMILES stringNC1=Nc2nc[nH]c2C(=S)N1
InChI1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI keyWYWHKKSPHMUBEB-UHFFFAOYSA-N
Gene Informationhuman ... IMPDH1(3614), IMPDH2(3615)

安全信息

象形图GHS06
警示用语:Danger
危险声明H301
预防措施声明P301 + P330 + P331 + P310
危险分类Acute Tox. 3 Oral
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
A4660Sigma-Aldrich6-ThioguanineHybri-Max, 50 ×, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma302.84元/2.5 MG;   展开

产品说明

应用

在杂交瘤形成应用中作为选择剂。

生化/生理作用

核糖基化并通过与天然嘌呤碱相同的途径磷酸化;作为核苷酸,抑制参与核酸合成的多种细胞过程。作为白血病的有效治疗方法已有悠久的历史。

重悬

10mL 无菌细胞培养基可复原一小瓶本品。储存液足以制备 500mL 培养基。最终工作浓度:30μM 2-氨基-6-巯基嘌呤。

法律信息

Hybri-Max is a trademark of sigma-aldrich Co. LLC

基本信息

经验(实验)分子式C5H5N5S
分子量167.19
Beilstein157765
EC 号205-827-2
MDL编号MFCD00233553
PubChem化学物质编号24890892
NACRESNA.75

产品性质

质量水平200
生物来源synthetic (organic)
等级Hybri-Max
无菌性γ-irradiated
产品线BioXtra
测定~98%
形式lyophilized powder
浓度50 ×
technique(s)cell culture | hybridoma: suitable
杂质 endotoxin, tested
mp≥300 ℃ (lit.)
溶解性1 M NaOH: 50 mg/mL, clear to slightly hazy
web metadata keyword.defaultSelection agent, purine antimetabolite, thiopurine, mutagen, cytotoxin
储存温度room temp
SMILES stringNC1=Nc2nc[nH]c2C(=S)N1
InChI1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI keyWYWHKKSPHMUBEB-UHFFFAOYSA-N
Gene Informationhuman ... IMPDH1(3614), IMPDH2(3615)

安全信息

象形图GHS06
警示用语:Danger
危险声明H301
预防措施声明P301 + P310
危险分类Acute Tox. 3 Oral
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
个人防护装备Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
BP878TioguanineBritish Pharmacopoeia (BP) Reference Standard2144.18元/100 MG;   展开

产品说明

一般描述

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

生化/生理作用

核糖基化并通过与天然嘌呤碱相同的途径磷酸化;作为核苷酸,抑制参与核酸合成的多种细胞过程。作为白血病的有效治疗方法已有悠久的历史。

包装

Unit quantity: 100 mg. Subject to change. The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity please visit British Pharmacopoeia

其他说明

Sales restrictions may apply.

基本信息

经验(实验)分子式C5H5N5S
分子量167.19
Beilstein157765
MDL编号MFCD00233553
NACRESNA.24

产品性质

等级pharmaceutical primary standard
manufacturer/tradenameBP
mp≥300 ℃ (lit.)
格式neat
储存温度2-8℃
SMILES stringNC1=Nc2nc[nH]c2C(=S)N1
InChI1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI keyWYWHKKSPHMUBEB-UHFFFAOYSA-N
Gene Informationhuman ... IMPDH1(3614), IMPDH2(3615)

安全信息

象形图GHS06
警示用语:Danger
危险声明H301
预防措施声明P264 - P270 - P301 + P310 + P330 - P405 - P501
危险分类Acute Tox. 3 Oral
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
358091Fluorochem2-Amino-1,7-dihydro-6H-purine-6-thione95+%418元/1g;   1078元/5g;   4378元/25g;   13882元/100g;   展开

基本信息

CAS Number154-42-7
MDL NumberMFCD00005568
Melting Point360℃

安全信息

图形或危害标志
危险性说明 H301: Toxic if swallowed.
H315: Causes skin irritation.
H319: Causes serious eye irritation.
H335: May cause respiratory irritation.
防范说明 P233: Keep container tightly closed.
P260: Do not breathe .
P261: Avoid breathing
P264: Wash hands thoroughly after handling.
P270: Do not eat, drink or smoke when using this product.
P271: Use only outdoors or in a well-ventilated area.
P280: Wear .
P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P302 + P352: IF ON SKIN: Wash with plenty of soap and water.
P304: IF INHALED: .
P304 + P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312: Call a POISON CENTER or doctor/physician if you feel unwell.
P321: Specific treatment (see . on this label).
P330: Rinse mouth.
P332 + P313: If skin irritation occurs: Get medical advice/ attention.
P337 + P313: If eye irritation persists: Get medical advice/attention.
P340: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P362: Take off contaminated clothing and wash before reuse.
P403: Store in a well-ventilated place.
P403 + P233: Store in a well-ventilated place. Keep container tightly closed.
P405: Store locked up.
P501: Dispose of contents/container to local regulations.
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