8-AZAGUANINE (BioDeep_00000325570)

Main id: BioDeep_00000175236

 

PANOMIX_OTCML-2023


代谢物信息卡片


8-AZAGUANINE

化学式: C4H4N6O (152.0446574)
中文名称: 8-氮杂鸟嘌呤
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C12=NNN=C1N=C(NC2=O)N
InChI: InChI=1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)

描述信息

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
D009676 - Noxae > D000963 - Antimetabolites
D000970 - Antineoplastic Agents
8-Azaguanine is a purine analogue that shows antineoplastic activity. 8-Azaguanine functions as an antimetabolite and easily incorporates into ribonucleic acids, interfering with normal biosynthetic pathways, thus inhibiting cellular growth[1].

同义名列表

1 个代谢物同义名

8-AZAGUANINE



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10 个数据库交叉引用编号

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代谢反应

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在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

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文献列表

  • I T Gatchell, R B Huntley, N P Schultes, G S Mourad. The guanine-hypoxanthine permease GhxP of Erwinia amylovora facilitates the influx of the toxic guanine derivative 6-thioguanine. Journal of applied microbiology. 2021 Jun; 130(6):2018-2028. doi: 10.1111/jam.14925. [PMID: 33152175]
  • Qiao-Ling Gong, Xin-Gen Hu, Guo-Yong Fang, Xin-Hua Li. Study of the interaction between 8-azaguanine and bovine serum albumin using optical spectroscopy and molecular modeling methods. Journal of molecular modeling. 2012 Feb; 18(2):493-500. doi: 10.1007/s00894-011-1069-5. [PMID: 21541747]
  • Makoto Kobayashi, Toshihide Matsumoto, Shinichiro Ryuge, Kengo Yanagita, Ryo Nagashio, Yoshitaka Kawakami, Naoki Goshima, Shi-Xu Jiang, Makoto Saegusa, Akira Iyoda, Yukitoshi Satoh, Noriyuki Masuda, Yuichi Sato. CAXII Is a sero-diagnostic marker for lung cancer. PloS one. 2012; 7(3):e33952. doi: 10.1371/journal.pone.0033952. [PMID: 22439015]
  • Carsten Bernard, Michaela Traub, H-Henning Kunz, Stefanie Hach, Oliver Trentmann, Torsten Möhlmann. Equilibrative nucleoside transporter 1 (ENT1) is critical for pollen germination and vegetative growth in Arabidopsis. Journal of experimental botany. 2011 Aug; 62(13):4627-37. doi: 10.1093/jxb/err183. [PMID: 21642237]
  • Se Wha Kang, Eun Mi Ahn, Youn-Soo Cha. Changes in lipid and carnitine concentrations following repeated fasting-refeeding in mice. Nutrition research and practice. 2010 Dec; 4(6):477-85. doi: 10.4162/nrp.2010.4.6.477. [PMID: 21286405]
  • Jianling Jin, Bo Liu, Hui Zhang, Xiao Tian, Yupin Cai, Peiji Gao. Mutagenicity of Chinese traditional medicine Semen Armeniacae amarum by two modified Ames tests. BMC complementary and alternative medicine. 2009 Nov; 9(?):43. doi: 10.1186/1472-6882-9-43. [PMID: 19912670]
  • Tyler A Mansfield, Neil P Schultes, George S Mourad. AtAzg1 and AtAzg2 comprise a novel family of purine transporters in Arabidopsis. FEBS letters. 2009 Jan; 583(2):481-6. doi: 10.1016/j.febslet.2008.12.048. [PMID: 19121308]
  • Andrew T Slack, Thareerat Kalambaheti, Meegan L Symonds, Michael F Dohnt, Renee L Galloway, Arnold G Steigerwalt, Wanpen Chaicumpa, Gaysorn Bunyaraksyotin, Scott Craig, Bruce J Harrower, Lee D Smythe. Leptospira wolffii sp. nov., isolated from a human with suspected leptospirosis in Thailand. International journal of systematic and evolutionary microbiology. 2008 Oct; 58(Pt 10):2305-8. doi: 10.1099/ijs.0.64947-0. [PMID: 18842846]
  • B G Corney, A T Slack, M L Symonds, M F Dohnt, C S McClintock, M R McGowan, L D Smythe. Leptospira weilii serovar Topaz, a new member of the Tarassovi serogroup isolated from a bovine source in Queensland, Australia. International journal of systematic and evolutionary microbiology. 2008 Oct; 58(Pt 10):2249-52. doi: 10.1099/ijs.0.64884-0. [PMID: 18842835]
  • Elton L L Roberts, Russell P Newton. Estimation of guanine deaminase using guanosine as a "prosubstrate". Analytical biochemistry. 2004 Jan; 324(2):250-7. doi: 10.1016/j.ab.2003.09.041. [PMID: 14690689]
  • Daniel E Sonenshine, Trevor Adams, Sandra A Allan, John McLaughlin, Francis X Webster. Chemical composition of some components of the arrestment pheromone of the black-legged tick, Ixodes scapularis (Acari: Ixodidae) and their use in tick control. Journal of medical entomology. 2003 Nov; 40(6):849-59. doi: 10.1603/0022-2585-40.6.849. [PMID: 14765662]
  • H Ren, H Endo, T Hayashi. The superiority of organically cultivated vegetables to general ones regarding antimutagenic activities. Mutation research. 2001 Sep; 496(1-2):83-8. doi: 10.1016/s1383-5718(01)00229-7. [PMID: 11551483]
  • S Grenacher, T Kröber, P M Guerin, M Vlimant. Behavioural and chemoreceptor cell responses of the tick, Ixodes ricinus, to its own faeces and faecal constituents. Experimental & applied acarology. 2001; 25(8):641-60. doi: 10.1023/a:1016145805759. [PMID: 12171273]
  • V S Reddy, C H Ford. Production of hybrids secreting bispecific antibodies recognising CEA and doxorubicin. Anticancer research. 1993 Nov; 13(6A):2077-83. doi: NULL. [PMID: 8297116]
  • R N Ramachandra, I Berczi, E S Rector, A H Sehon. Development and characterization of ouabain-resistant human fusion partners. Journal of immunological methods. 1991 Aug; 142(1):21-9. doi: 10.1016/0022-1759(91)90288-q. [PMID: 1655911]
  • N Babudri, G Morpurgo. Frequency of spontaneous and induced recessive mutations in a diploid strain of Aspergillus nidulans. Mutation research. 1990 Jun; 230(2):187-95. doi: 10.1016/0027-5107(90)90056-a. [PMID: 2197553]
  • V P Grachev, M A Zaval'nyĭ, V D Popova, M K Khanina, G P Baranova. [RAMT cell line as a substrate for the propagation of vaccinal viral strains]. Voprosy virusologii. 1986 Nov; 31(6):718-22. doi: NULL. [PMID: 3825095]
  • M Orikasa, K Takasugi, A Fujiwara, S Motoda, F Shimizu. A simple method for efficiently establishing 8-azaguanine-resistant mutant human leukemia and myeloma cell lines. Journal of immunological methods. 1985 Dec; 85(1):75-85. doi: 10.1016/0022-1759(85)90275-3. [PMID: 3908563]
  • J J Berman, C Tong, G M Williams. Toxicity of 6-thioguanine and 8-azaguanine to non-dividing liver cell cultures. Cell biology and toxicology. 1985 Jan; 1(2):67-73. doi: 10.1007/bf00717792. [PMID: 3917127]
  • P G Plagemann, R M Wohlhueter. Metabolic properties of an azaguanine-resistant variant of Chinese hamster ovary cells (azarts) with normal levels of hypoxanthine-guanine phosphoribosyltransferase activity. Journal of cellular biochemistry. 1985; 27(2):109-20. doi: 10.1002/jcb.240270205. [PMID: 3988817]
  • C L Lee, S H Lee, K R Rozee, S H Chen. 8-Azaguanine resistant African green monkey kidney cell mutants (Vero 153): isolation and characterization. In vitro. 1983 May; 19(5):416-20. doi: 10.1007/bf02619558. [PMID: 6190732]
  • V I Stobetskiĭ, V P Grachev, L L Mironova, V G Chernikov. [African green monkey cell line RAMP simultaneously resistant to 8-azaguanine, 6-mercaptopurine, and 6-thioguanine]. Biulleten' eksperimental'noi biologii i meditsiny. 1982 Oct; 94(10):113-5. doi: . [PMID: 6890862]
  • S Iapalucci-Espinoza, M T Franze-Fernandez. Regulation of rRNA synthesis and processing in animal cells. Effect of nucleoside analogues. The Biochemical journal. 1982 Feb; 202(2):325-32. doi: 10.1042/bj2020325. [PMID: 6212050]
  • S Miyamoto, H Ogawa, H Shiraki, H Nakagawa. Guanine deaminase from rat brain. Purification, characteristics, and contribution to ammoniagenesis in the brain. Journal of biochemistry. 1982 Jan; 91(1):167-76. doi: 10.1093/oxfordjournals.jbchem.a133673. [PMID: 7040358]
  • P G Plagemann, R Marz, R M Wohlhueter, J C Graff, J M Zylka. Facilitated transport of 6-mercaptopurine and 6-thioguanine and non-mediated permeation of 8-azaguanine in Novikoff rat hepatoma cells and relationship to intracellular phosphoribosylation. Biochimica et biophysica acta. 1981 Sep; 647(1):49-62. doi: 10.1016/0005-2736(81)90294-7. [PMID: 7197551]
  • S Ito, T Takaoka, H Mori, A Teruo. A sensitive new method for measurement of guanase with 8-azaguanine in bicine bis-hydroxy ethyl glycine buffer as substrate. Clinica chimica acta; international journal of clinical chemistry. 1981 Sep; 115(2):135-44. doi: 10.1016/0009-8981(81)90069-3. [PMID: 7285360]
  • J Brennand, S McMillan, M Fox. Effects of metabolic inhibitors on cel lethality and mutation induction in Chinese hamster cells. II. The effect of posttreatment with non-toxic concentrations of thymidine. Chemico-biological interactions. 1981 Jul; 36(1):89-106. doi: 10.1016/0009-2797(81)90031-4. [PMID: 7249152]
  • F Piquard, A Schaefer, P Haberey, M Chanez, J Peret. The effects of dietary self-selection upon the overshoot phenomenon in starved-refed rats. The Journal of nutrition. 1979 Jun; 109(6):1035-44. doi: 10.1093/jn/109.6.1035. [PMID: 448442]
  • O P van Diggelen, T F Donahue, S I Shin. Basis for differential cellular sensitivity to 8-azaguanine and 6-thioguanine. Journal of cellular physiology. 1979 Jan; 98(1):59-71. doi: 10.1002/jcp.1040980108. [PMID: 762202]
  • N G Westberg, E Rosén, J Waldenström. Recessive X-linked hyperuricemia with gout and renal damage, normal activity of hypoxanthine phosphoribosyltransferase and resistance to azaguanine. Acta medica Scandinavica. 1979; 205(3):163-7. doi: 10.1111/j.0954-6820.1979.tb06024.x. [PMID: 425844]
  • J E Lever. Genetic alteration in the (Na+ + K+) ATPase transport system expressed in human lymphoblasts and their isolated plasma membranes. Journal of cellular physiology. 1976 Dec; 89(4):811-4. doi: 10.1002/jcp.1040890448. [PMID: 137909]
  • A R Peterson, D F Krahn, H Peterson, C Heidelberger, B K Bhuyan, L H Li. The influence of serum components on the growth and mutation of Chinese hamster cells in medium containing 8-azaguanine. Mutation research. 1976 Sep; 36(3):345-56. doi: 10.1016/0027-5107(76)90244-x. [PMID: 958230]
  • J E Lever, J E Seegmiller. Ouabain-resistant human lymphoblastoid lines altered in the (Na+ + K+)-dependent ATPase membrane transport system. Journal of cellular physiology. 1976 Jul; 88(3):343-52. doi: 10.1002/jcp.1040880310. [PMID: 131808]
  • A Watanabe, M Miyazaki, K Taketa. Differential mechanisms of increased alpha 1-fetoprotein production in rats following carbon tetrachloride injury and partial hepatectomy. Cancer research. 1976 Jul; 36(7 PT 1):2171-5. doi: NULL. [PMID: 58715]
  • O Nikaido, M Fox. The relative effectiveness of 6-thioguanine and 8-azaguanine in selecting resistant mutants from two V79 Chinese hamster cells in vitro. Mutation research. 1976 Jun; 35(2):279-87. doi: 10.1016/0027-5107(76)90192-5. [PMID: 14997604]
  • J Thacker, M A Stephens, A Stretch. Factors affecting the efficiency of purine analogues as selective agents for mutants of mammalian cells induced by ionising radiation. Mutation research. 1976 Jun; 35(3):465-78. doi: 10.1016/0027-5107(76)90208-6. [PMID: 934168]
  • J H Carver, W C Dewey, L E Hopwood. X-ray-induced mutants resistant to 8-azaguanine. II. Cell cycle dose response. Mutation research. 1976 Mar; 34(3):465-79. doi: 10.1016/0027-5107(76)90223-2. [PMID: 1264111]
  • J H Carver, W C Dewey, L E Hopwood. X-ray-induced mutants resistant to 8-azaguanine. I. Effects of cell density and expression time. Mutation research. 1976 Mar; 34(3):447-63. doi: 10.1016/0027-5107(76)90222-0. [PMID: 1264110]
  • B Galanti, M Russo, S Nardiello, G Giusti. Further observations on the properties of serum and tissue guanase from man and some animal species. Optimum pH and activation energy in the presence of 8-azaguanine. Enzyme. 1976; 21(4):342-8. doi: 10.1159/000458877. [PMID: 7449]
  • M I Marshak, N B Varshaver, N I Shapiro. Induction of gene mutations and chromosomal aberrations by simian virus 40 in cultured mammalian cells. Mutation research. 1975 Dec; 30(3):383-96. doi: 10.1016/0027-5107(75)90009-3. [PMID: 172787]
  • B C Myhr, J A Dipalo. Requirement for cell dispersion prior to selection of induced azaguanine-resistant colonies of Chinese hamster cells. Genetics. 1975 May; 80(1):157-69. doi: 10.1093/genetics/80.1.157. [PMID: 1093934]
  • M I Marshak, N B Varshaver, N I Shapiro. [Mutagenesis under the influence of simian virus 40 (SV40). II. Induction of mutations for resistance to analogs of purine bases in human and Chinese hamster cells]. Genetika. 1975; 11(2):93-104. doi: NULL. [PMID: 182615]
  • A A van Zeeland, J W Simons. The effect of calf serum on the toxicity of 8-azaguanine. Mutation research. 1975 Jan; 27(1):135-8. doi: 10.1016/0027-5107(75)90283-3. [PMID: 1121314]
  • M I Marashak, N B Varshaver, N I Shapiro. [Mutagenesis under the influence of simian virus 40 (SV40). II. Induct?ION OF MUTATIONS RESULTING IN RESISTANCE TO PURINE BASE ANALOGS IN HUMAN AND Chinese hamster cells]. Genetika. 1975; 11(2):92-104. doi: NULL. [PMID: 178572]
  • D Wild. Serum effect on the yield of chemically induced 8-azaguanine-resistant mutants in Chinese hamster cell cultures. Mutation research. 1974 Nov; 25(2):229-34. doi: 10.1016/0027-5107(74)90022-0. [PMID: 4431422]
  • K Tejima, K Uchida, Y Miyashita. [Evaluation of the method of serum guanase analysis and its clinical application]. Rinsho byori. The Japanese journal of clinical pathology. 1974 Oct; 22(10 Suppl):80. doi: NULL. [PMID: 4475998]
  • B Szepesi, C D Berdanier, O E Michaelis. Effect of age on the responses to starvation-refeeding in the rat. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1974 Oct; 147(1):195-200. doi: 10.3181/00379727-147-38310. [PMID: 4438323]
  • A R Peterson, H Peterson, C Heidelberger. The influence of serum components on the growth and mutation of Chinese hamster cells in medium containing aminopterin. Mutation research. 1974 Jul; 24(1):25-33. doi: 10.1016/0027-5107(74)90043-8. [PMID: 4843973]
  • M Caboche. Comparison of the frequencies of spontaneous and chemically-induced 5-bromodeoxyuridine-resistance mutations in wild-type and revertant BHK-21-13 cells. Genetics. 1974 Jun; 77(2):309-22. doi: 10.1093/genetics/77.2.309. [PMID: 4367878]
  • P M Naha. Isolation of temperature-sensitive mutants of mammalian cells. Methods in cell biology. 1974; 8(0):41-6. doi: 10.1016/s0091-679x(08)60442-2. [PMID: 4366066]
  • H Iwata, I Yamamoto, E Goda, K Morita, M Nakamura. Potent competitive uricase inhibitors--2,8-diazahypoxanthine and related compounds. Biochemical pharmacology. 1973 Sep; 22(18):2237-45. doi: 10.1016/0006-2952(73)90004-x. [PMID: 4733677]
  • P J Benke, N Herrick, A Hebert. Hypoxanthine-guanine phosphoribosyltransferase variant associated with accelerated purine synthesis. The Journal of clinical investigation. 1973 Sep; 52(9):2234-40. doi: 10.1172/jci107409. [PMID: 4353774]
  • G Ellis, R J Spooner, D M Goldberg. Automated kinetic assays for routine determination of adenosine deaminase and guanase activities of human serum. Clinica chimica acta; international journal of clinical chemistry. 1973 Aug; 47(1):75-87. doi: 10.1016/0009-8981(73)90062-4. [PMID: 4795850]
  • M N Musa, G M Lower, G T Bryan. Colorimetric method for determination of guanazole in blood and urine. Journal of pharmaceutical sciences. 1973 May; 62(5):831-2. doi: 10.1002/jps.2600620533. [PMID: 4705699]
  • D Yakar, J F Holland, R R Ellison, A Freeman. Clinical pharmacological trial of guanazole. Cancer research. 1973 May; 33(5):972-5. doi: NULL. [PMID: 4512954]
  • S Shin, R Caneva, C L Schildkraut, H P Klinger, M Siniscalco. Cells with phosphoribosyl transferase activity recovered from mouse cells resistant to 8-azaguanine. Nature: New biology. 1973 Feb; 241(111):194-6. doi: 10.1038/newbio241194a0. [PMID: 4512582]
  • A E De Maggio, V Raghavan. Photomorphogenesis and nucleic acid metabolism in fern gametophytes. Advances in morphogenesis. 1973; 10(?):227-63. doi: 10.1016/b978-0-12-028610-2.50009-5. [PMID: 4581328]
  • G Ellis, D M Goldberg. Assay of human serum and liver guanase activity with 8-azaguanine as substrate. Clinica chimica acta; international journal of clinical chemistry. 1972 Mar; 37(?):47-52. doi: 10.1016/0009-8981(72)90414-7. [PMID: 5022113]
  • B Szepesi, C D Berdanier, S K Diachenko, P B Moser. Effect of length of starvation, refeeding, and 8-azaguanine on serum insulin and NADP-linked dehydrogenases of rat liver. The Journal of nutrition. 1971 Sep; 101(9):1147-51. doi: 10.1093/jn/101.9.1147. [PMID: 4398528]
  • B Szepesi, C D Berdanier, M Egawa. Evidence for increased constitutiveness of NADP-linked dehydrogenases in the starved-refed rat. The Journal of nutrition. 1971 Jul; 101(7):863-7. doi: 10.1093/jn/101.7.863. [PMID: 4397513]
  • B Szepesi, C D Berdanier, S K Diachenko, P B Moser. Effect of repeated starvation on serum insulin level and the enzyme overshoot in liver. Canadian journal of biochemistry. 1971 Mar; 49(3):393-5. doi: 10.1139/o71-057. [PMID: 5549741]
  • J F Watkins. The effects of some metabolic inhibitors on the ability of SV40 virus in transformed cells to be detected by cell fusion. Journal of cell science. 1970 May; 6(3):721-37. doi: 10.1242/jcs.6.3.721. [PMID: 4318033]
  • M E Schwochau, L A Hadwiger. Regulation of gene expression by actinomycin D and other compounds which change the conformation of DNA. Archives of biochemistry and biophysics. 1969 Oct; 134(1):34-41. doi: 10.1016/0003-9861(69)90247-1. [PMID: 5345595]
  • B S Uteshev, B V Pinegin, A G Kalinkovich, V V Lebedev. [Depression of immunological reactivity with 8-azaguanine]. Farmakologiia i toksikologiia. 1969 May; 32(3):308-12. doi: NULL. [PMID: 5810948]
  • H B Nevinny, T C Hall. Chemotherapy with hydroxyurea (NSC-32065) in renal cell carcinoma. The Journal of clinical pharmacology and the journal of new drugs. 1968 Nov; 8(6):352-9. doi: 10.1002/j.1552-4604.1968.tb00110.x. [PMID: 4883783]
  • F Melani, G Ramponi, M Farnararo, E Cocucci, A Guerritore. Regulation by phosphate of alkaline phosphatase in rat kidney. Biochimica et biophysica acta. 1967 Apr; 138(2):411-20. doi: 10.1016/0005-2787(67)90500-x. [PMID: 6048836]
  • R C Johnson, V G Harris. Antileptospiral activity of serum. II. Leptospiral virulence factor. Journal of bacteriology. 1967 Feb; 93(2):513-9. doi: 10.1128/jb.93.2.513-519.1967. [PMID: 6020558]
  • C WU. GLUTAMINE SYNTHETASE. 3. FACTORS CONTROLLING ITS ACTIVITY IN THE DEVELOPING RAT. Archives of biochemistry and biophysics. 1964 Jul; 106(?):394-401. doi: 10.1016/0003-9861(64)90206-1. [PMID: 14217186]
  • J K Heyes. The role of nucleic acids in cell growth and differentiation. Symposia of the Society for Experimental Biology. 1963; 17(?):40-57. doi: ". [PMID: 5849044]
  • I E YOUNG, P C FITZ-JAMES. Chemical and morphological studies of bacterial spore formation. III. The effect of 8-azaguanine on spore and parasporal protein formation in Bacillus cereus var. alesti. The Journal of biophysical and biochemical cytology. 1959 Dec; 6(?):499-506. doi: 10.1083/jcb.6.3.499. [PMID: 13846632]
  • Y HOTTA, S OSAWA. Control of differentiation in the fern gametophyte by amino acid analogs and 8-azaguanine. Experimental cell research. 1958 Aug; 15(1):85-94. doi: 10.1016/0014-4827(58)90064-8. [PMID: 13574161]
  • G DEYSSON, R TRUHAUT, M DEYSSON. [Effect of various purine antagonists (2-6-diaminopurine, 8-azaguanine and 6-mercaptopurine) on plant cell division]. Bulletin de la Societe de chimie biologique. 1956 Jun; 38(2-3):535-46. doi: ". [PMID: 13342757]