For research use only. Not for therapeutic Use.
Tubercidin（Cat No.:I004606）, also known as 7-Deazaadenosine, is an adenosine analog that exhibits antibiotic properties. It is derived from the bacterium Streptomyces tubercidicus. Tubercidin functions by interfering with nucleic acid synthesis, specifically inhibiting RNA synthesis. Its structural similarity to adenosine allows it to be incorporated into RNA molecules, leading to the disruption of essential cellular processes. Tubercidin has shown potential as an antimicrobial agent against various pathogens and has also been investigated for its antiviral and antitumor properties.
| Catalog Number | I004606 |
| CAS Number | 69-33-0 |
| Molecular Formula | C11H14N4O4 |
| Purity | ≥95% |
| Target | Antibacterial |
| Solubility | 10 mM in H2O |
| Storage | Room temperature |
| IUPAC Name | (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
| InChI | InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1 |
| InChIKey | HDZZVAMISRMYHH-KCGFPETGSA-N |
| SMILES | C1=CN(C2=NC=NC(=C21)N)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O |
| Reference | </br>1:Characterization of a Novel Endoplasmic Reticulum Protein Involved in Tubercidin Resistance in Leishmania major. Aoki JI, Coelho AC, Muxel SM, Zampieri RA, Sanchez EM, Nerland AH, Floeter-Winter LM, Cotrim PC.PLoS Negl Trop Dis. 2016 Sep 8;10(9):e0004972. doi: 10.1371/journal.pntd.0004972. eCollection 2016 Sep. PMID: 27606425 Free PMC Article</br>2:Actinopolysporins A-C and tubercidin as a Pdcd4 stabilizer from the halophilic actinomycete Actinopolyspora erythraea YIM 90600. Zhao LX, Huang SX, Tang SK, Jiang CL, Duan Y, Beutler JA, Henrich CJ, McMahon JB, Schmid T, Blees JS, Colburn NH, Rajski SR, Shen B.J Nat Prod. 2011 Sep 23;74(9):1990-5. doi: 10.1021/np200603g. Epub 2011 Aug 26. PMID: 21870828 Free PMC Article</br>3:7-(5-Methyl-sulfanyl-β-d-erythrofuran-osyl)-7H-pyrrolo-[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O). Gainsford GJ, Fröhlich RF, Evans GB.Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 18;66(Pt 7):o1688-9. doi: 10.1107/S1600536810020179. PMID: 21587912 Free PMC Article</br>4:Efficacy of the tubercidin antileishmania action associated with an inhibitor of the nucleoside transport. Aoki JI, Yamashiro-Kanashiro EH, Ramos DC, Cotrim PC.Parasitol Res. 2009 Jan;104(2):223-8. doi: 10.1007/s00436-008-1177-z. Epub 2008 Sep 12. PMID: 18787843 </br>5:Quantitative structure-activity relationship study of 5-iodo- and diaryl-analogues of tubercidin: inhibitors of adenosine kinase. Singh P, Kumar R, Sharma BK.J Enzyme Inhib Med Chem. 2003 Oct;18(5):395-402. PMID: 14692505 </br>6:The adenosine analog tubercidin inhibits glycolysis in Trypanosoma brucei as revealed by an RNA interference library. Drew ME, Morris JC, Wang Z, Wells L, Sanchez M, Landfear SM, Englund PT.J Biol Chem. 2003 Nov 21;278(47):46596-600. Epub 2003 Sep 12. PMID: 12972414 Free Article</br>7:Study on the synthesis and PKA-I binding activities of 5-alkynyl tubercidin analogues. Zhang L, Zhang Y, Li X, Zhang L.Bioorg Med Chem. 2002 Apr;10(4):907-12. PMID: 11836097 </br>8:Syntheses of puromycin from adenosine and 7-deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair. Robins MJ, Miles RW, Samano MC, Kaspar RL.J Org Chem. 2001 Nov 30;66(24):8204-10. PMID: 11722226 </br>9:Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin. Nishimura N, Kato A, Maeba I.Carbohydr Res. 2001 Mar 9;331(1):77-82. PMID: 11284507 </br>10:Purification and characterization of GTP cyclohydrolase I from Streptomyces tubercidicus, a producer of tubercidin. Yoo JC, Han JM, Ko OH, Bang HJ.Arch Pharm Res. 1998 Dec;21(6):692-7. PMID: 9868539 |
