8-Azaguanine 8-氮鸟嘌呤

CAS 134-58-7 MFCD00056937

化学结构图

134-58-7
SMILES: Nc1nc2[nH]nnc2c(=O)[nH]1

化学属性

Mol. FormulaC4H4N6O
Mol. Weight152.11
Density1.422
Melting Point>300°C
Appearance lyophilized powder
SolubilitySoluble in water, DMSO (6 mg/ml at 25 °C), ethanol (<1 mg/ml at 25 °C), and NaOH (1 mol/l). Insoluble in ether.
Boiling Point274.55 °C at 760 mmHg

别名和识别编码

Chemical Name8-Azaguanine
CAS Number134-58-7
EC Number205-148-1
Beilstein Registry Number171098
MDL NumberMFCD00056937
Synonym 8-Azaguanine {LY} 8-Azaguanine {} {LY} 8-Azaguanine {} {} {LY} 8-Azaguanine {} {} {} {LY} 8-Azaguanine {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 8-Azaguanine {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID135403646
Reaxys-RN171098
Merck Number896
Chemical Name Translation8-氮鸟嘌呤
Wiswesser Line NotationT56 BNNM FVM INJ HZ
LabNetwork Molecule IDLN00191892
InChIInChI=1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
Canonical SMILESO=C1C(N=NN2)=C2N=C(N)N1
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分类

  • {SNA} Conditioned Media, Media Supplements and Reagents, Hybridoma Platform, Hybridoma Reagents, 无血清培养基, 细胞培养, 试剂和添加剂
  • {SNA} Cell Culture, Conditioned Media, Media Supplements and Reagents, Hybridoma Platform, Hybridoma Reagents, Reagents and Supplements, Serum-free Media
  • {Chemicalbook} 生物化学品: 核酸类: 核酸碱基及其衍生物

产品应用

  • A triazolo guanine analog that inhibits purine nucleotide biosynthesis.

相关文献及参考

  • [1]. Dourado M, et al. CD26/DPPIV expression and 8-azaguanine response in T-acute lymphoblastic leukaemia cell lines in culture. Pathophysiology. 2007 May;14(1):3-10.

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P301+P312+P330
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H302 Harmful if swallowed 吞食有害
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSXZ6157000
Hazard Codes Xn
Storage condition -20°C {LY} -20°C {} {LY} -20°C {} {} {LY} -20°C {} {} {} {LY} -20°C {} {} {} {} {LY} -20°C {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
TYPE OF TEST            : LD10 - Lethal Dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 90 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PMDCAY Progress in Medical Chemistry.  (Elsevier Science Pub. Co., Inc., 52
   Vanderbilt Ave., New York, NY 10017)  V.1-    1961- Volume(issue)/page/year:
   7,69,1970

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 30 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JAJAAA Journal of Antibiotics, Series A.  (Tokyo, Japan)  V.6-20, 1953-67.
   For publisher information, see JANTAJ.  Volume(issue)/page/year: 13,19,1960

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 5,193,1981

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ADTEAS Advances in Teratology.  (New York, NY)  V.1-5, 1966-72.
   Discontinued.  Volume(issue)/page/year: 3,181,1968

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Fibroblast
DOSE/DURATION           : 500 ug/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 88,241,1981

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 150 mg/L
REFERENCE :
   CSHSAZ Cold Spring Harbor Symposia on Quantitative Biology.  (Cold Spring
   Harbor Laboratory, POB 100, Cold Spring Harbor, NY 11724)  V.1-    1933-
   Volume(issue)/page/year: 16,337,1952

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 66 umol/L
REFERENCE :
   CJBBDU Canadian Journal of Biochemistry and Cell Biology.  (National
   Research Council of Canada, Publication Sales and Distribution, Ottawa ON
   K1A OR6, Canada)  V.61-     1983-  Volume(issue)/page/year: 62,280,1984

TYPE OF TEST            : Mu

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Leukocyte
DOSE/DURATION           : 1 umol/L
REFERENCE :
   AEZRA2 Advances in Enzyme Regulation.  (Pergamon Press Inc., Maxwell House,
   Fai

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 37500 ng/well
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 260,349,1991

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - hamster Lung
DOSE/DURATION           : 30 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 80 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)
REFERENCE :
   JEEMAF Journal of Embryology and Experimental Morphology.  (Essex, UK)
   V.1-98, 1953-86. For Publisher information, see DEVPED
   Volume(issue)/page/year: 6,593,1958

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 80 mg/kg
SEX/DURATION            : female 8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
REFERENCE :
   JEEMAF Journal of Embryology and Experimental Morphology.  (Essex, UK)
   V.1-98, 1953-86. For Publisher information, see DEVPED
   Volume(issue)/page/year: 6,593,1958

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 50 mg/kg
SEX/DURATION            : male 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
REFERENCE :
   HIKYAJ Hinyokika Kiyo.  Journal of Urology.   (Kyoto Daigaku Igakubu,
   Hinyokikagaku Kyoshitsu, 54 Kawara-machi, Shogain, Sakyo-ku, Kyoto 606,
   Japan)  V.1-    1955-  Volume(issue)/page/year: 12,1339,1966

其他信息

  • 图谱信息:8-氮鸟嘌呤(134-58-7)质谱(MS) 8-氮鸟嘌呤(134-58-7)红外图谱(IR2) 8-氮鸟嘌呤(134-58-7)红外图谱(IR1)
  • Sigma Aldrich:134-58-7(sigmaaldrich)
  • Azaguanine-8是嘌呤类似物,具有抗肿瘤活性,在代谢中与鸟嘌呤竞争。
  • 方法一:由2,4-二氨基-6-羟基嘧啶经亚硝化、还原、重氮化、环合而得。(1)亚硝化得到2,4-二氨基-5-亚硝基-6-羟基嘧啶:在15℃以下,将亚硝酸钠加至2,4-二氨基-6-羟基嘧啶的水溶液中,滴加浓盐酸,析出玫瑰红色沉淀,pH约为3.5。过滤,水洗至中性,得2,4-二氨基-5-亚硝基-6-羟基嘧啶(亚硝基物)。(2)还原得到2,4,5-三氨基-6-羟基嘧啶硫酸盐(三氨基物):将亚硝基物混悬于水,搅拌下逐渐投入保险粉。随后加入氢氧化钠溶液,使pH=9,加热至沸,使反应液由红色变为浅黄色。加活性炭脱色,过滤。滤液冷却后,用硫酸调至刚果红呈酸性,析出黄色沉淀。过滤,用乙醇洗涤,得三氨基物。(3)重氮化、环合得8-氮杂鸟嘌呤:将三氨基物悬浮于水中,加氢氧化钠溶液,加热溶解。然后加入亚硝酸钠,搅拌溶解后加冰醋酸。加热至90℃保温反应1h。冷却,过滤,得8-氮杂鸟嘌呤粗品,经精制得成品。
  • 毒性分级:中毒
  • TCI Shanghai:8-氮鸟嘌呤 8-Azaguanine,>;98.0%(LC)(T)(134-58-7)
  • 用途一:抗癌药。为嘌呤抗代谢物,能抑制微生物、病毒、肿瘤细胞的增殖。不良反应有恶心、呕吐、食欲不振、腹泻、头痛、口渴、皮肤红斑、面红、白细胞减少、全身倦怠、皮疹、出血斑点。骨髓抑制轻微,并有肾损伤、心律不齐及心肌梗死。
  • 8-氮鸟嘌呤价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 K1141001 8-氮鸟嘌呤 1g 2761元 2011/04/16 A0625 8-氮鸟嘌呤 8-Azaguanine 5G 1540元 2011/04/16 A0625 8-氮鸟嘌呤 8-Azaguanine 1G 515元
  • 上游原料:连二亚硫酸钠 --> 直接红 28 --> 硝基物 --> 氨基物 --> 2,4-二氨基-6-羟基嘧啶
  • F:10-23
  • 急性毒性:腹腔-大鼠LD50: 1000 毫克/公斤; 口服-小鼠LD50: 1500 毫克/公斤
  • 灭火剂:干粉、泡沫、砂土、二氧化碳, 雾状水
  • MOL 文件:134-58-7.mol
  • 8-氮鸟嘌呤
  • 储运特性:库房通风低温干燥
  • 用途二:医药中间体,用于生产抗肿瘤药癌敌-M。
  • 可燃性危险特性:可燃;燃烧产生有毒氮氧化物烟雾
  • 类别:有毒物品

系列性分类


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