Tubercidin | CAS#69-33-0 | DNA/RNA Synthesis inhibitor

Tubercidin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 329643

CAS#: 69-33-0

Description: Tubercidin is a DNA/RNA Synthesis inhibitor. Tubercidin is a toxic adenosine analog with antiviral, antitrypanosomal, and antifungal functions. It inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal, inhibits mammalian SAH hydrolase (SAHH), and blocks purine biosynthesis in Candida famata.

Chemical Structure

Tubercidin

CAS# 69-33-0

Instruction

Theoretical Analysis

MedKoo Cat#: 329643
Name: Tubercidin
CAS#: 69-33-0
Chemical Formula: C11H14N4O4
Exact Mass: 266.10
Molecular Weight: 266.257
Elemental Analysis: C, 49.62; H, 5.30; N, 21.04; O, 24.04

Price and Availability

Size	Price	Availability
25mg	USD 150	2 Weeks
50mg	USD 250	2 Weeks
100mg	USD 450	2 Weeks
200mg	USD 700	2 Weeks
500mg	USD 1550	2 Weeks
1g	USD 2750	2 Weeks
2g	USD 4250
5g	USD 7650
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Tubercidin; Antibiotic XK 101-1; B 120121; NSC 56408; SKI 26996; Sparsomycin A; TBC; Tubercidin; Tubercidine; U 10071; U-10071; U10071;

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key: HDZZVAMISRMYHH-KCGFPETGSA-N

InChi Code: 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

SMILES Code: NC1=NC=NC2=C1C=CN2[C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Tubercidin inhibits glycolysis in Trypanosoma brucei. Tubercidin inhibits both chemotaxis and chemotaxis-dependent cell streaming of Dictyostelium, and chemotaxis of neutrophils at concentrations that have little effect on cell viability

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 266.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. Actinopolysporins A-C and tubercidin as a Pdcd4 stabilizer from the halophilic actinomycete Actinopolyspora erythraea YIM 90600. J Nat Prod. 2011 Sep 23;74(9):1990-5. doi: 10.1021/np200603g. Epub 2011 Aug 26. PubMed PMID: 21870828; PubMed Central PMCID: PMC3179765.

2: Kolassa N, Jakobs ES, Buzzell GR, Paterson AR. Manipulation of toxicity and tissue distribution of tubercidin in mice by nitrobenzylthioinosine 5'-monophosphate. Biochem Pharmacol. 1982 May 15;31(10):1863-74. PubMed PMID: 7104018.

3: el Kouni MH, Diop D, O'Shea P, Carlisle R, Sommadossi JP. Prevention of tubercidin host toxicity by nitrobenzylthioinosine 5'-monophosphate for the treatment of schistosomiasis. Antimicrob Agents Chemother. 1989 Jun;33(6):824-7. PubMed PMID: 2764531; PubMed Central PMCID: PMC284239.

4: Drew ME, Morris JC, Wang Z, Wells L, Sanchez M, Landfear SM, Englund PT. The adenosine analog tubercidin inhibits glycolysis in Trypanosoma brucei as revealed by an RNA interference library. J Biol Chem. 2003 Nov 21;278(47):46596-600. Epub 2003 Sep 12. PubMed PMID: 12972414.

5: Dovey HF, McKerrow JH, Wang CC. Action of tubercidin and other adenosine analogs on Schistosoma mansoni schistosomules. Mol Biochem Parasitol. 1985 Aug;16(2):185-98. PubMed PMID: 3929087.

6: Zmurko J, Marques RE, Schols D, Verbeken E, Kaptein SJ, Neyts J. The Viral Polymerase Inhibitor 7-Deaza-2'-C-Methyladenosine Is a Potent Inhibitor of In Vitro Zika Virus Replication and Delays Disease Progression in a Robust Mouse Infection Model. PLoS Negl Trop Dis. 2016 May 10;10(5):e0004695. doi: 10.1371/journal.pntd.0004695. eCollection 2016 May. PubMed PMID: 27163257; PubMed Central PMCID: PMC4862633.

7: Kurogi Y, Matsuo Y, Mihara Y, Yagi H, Shigaki-Miyamoto K, Toyota S, Azuma Y, Igarashi M, Tani T. Identification of a chemical inhibitor for nuclear speckle formation: implications for the function of nuclear speckles in regulation of alternative pre-mRNA splicing. Biochem Biophys Res Commun. 2014 Mar 28;446(1):119-24. doi: 10.1016/j.bbrc.2014.02.060. Epub 2014 Feb 22. PubMed PMID: 24569078.

8: Mooberry SL, Stratman K, Moore RE. Tubercidin stabilizes microtubules against vinblastine-induced depolymerization, a taxol-like effect. Cancer Lett. 1995 Sep 25;96(2):261-6. PubMed PMID: 7585466.

9: Jamoulle JC, Imai J, Lesiak K, Torrence PF. Synthesis and biological activity of tubercidin analogues of ppp5'A2'p(5'A2'p)n5'A. Biochemistry. 1984 Jun 19;23(13):3063-9. PubMed PMID: 6466631.

10: Kim S, Kim E, Hong JH. The first synthesis of 4'-branched 5'-deoxycarbocyclic 9-deazaadenosine and phosphonic acids as antiviral agents. Nucleosides Nucleotides Nucleic Acids. 2015;34(3):163-79. doi: 10.1080/15257770.2014.975245. PubMed PMID: 25710354.

11: Fustin JM, Doi M, Yamaguchi Y, Hida H, Nishimura S, Yoshida M, Isagawa T, Morioka MS, Kakeya H, Manabe I, Okamura H. RNA-methylation-dependent RNA processing controls the speed of the circadian clock. Cell. 2013 Nov 7;155(4):793-806. doi: 10.1016/j.cell.2013.10.026. PubMed PMID: 24209618.

12: Evans FE, Sarma RH. The aqueous solution conformation of tubercidin and tubercidin 5'-phosphate. Cancer Res. 1975 Jun;35(6):1458-63. PubMed PMID: 1131818.

13: Eyer L, Valdés JJ, Gil VA, Nencka R, Hřebabecký H, Šála M, Salát J, Černý J, Palus M, De Clercq E, Růžek D. Nucleoside inhibitors of tick-borne encephalitis virus. Antimicrob Agents Chemother. 2015 Sep;59(9):5483-93. doi: 10.1128/AAC.00807-15. Epub 2015 Jun 29. PubMed PMID: 26124166; PubMed Central PMCID: PMC4538560.

14: Cass CE, King KM, Montaño JT, Janowska-Wieczorek A. A comparison of the abilities of nitrobenzylthioinosine, dilazep, and dipyridamole to protect human hematopoietic cells from 7-deazaadenosine (tubercidin). Cancer Res. 1992 Nov 1;52(21):5879-86. PubMed PMID: 1394215.

15: Wang Q, Wei H, Du J, Cao Y, Zhang N, Liu X, Liu X, Chen D, Ma W. H3 Thr3 phosphorylation is crucial for meiotic resumption and anaphase onset in oocyte meiosis. Cell Cycle. 2016;15(2):213-24. doi: 10.1080/15384101.2015.1121330. Epub 2015 Dec 4. PubMed PMID: 26636626; PubMed Central PMCID: PMC4825905.

16: De Ornellas S, Slattery JM, Edkins RM, Beeby A, Baumann CG, Fairlamb IJ. Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs. Org Biomol Chem. 2015 Jan 7;13(1):68-72. doi: 10.1039/c4ob02081b. PubMed PMID: 25382270.

17: Takano S, Tsuzuki T, Murayama T, Sakurai T, Fukuda H, Arisawa M, Shuto S. Synthesis of 7-Deaza-cyclic Adenosine-5'-diphosphate-carbocyclic-ribose and Its 7-Bromo Derivative as Intracellular Ca(2+)-Mobilizing Agents. J Org Chem. 2015 Jul 2;80(13):6619-27. doi: 10.1021/acs.joc.5b00723. Epub 2015 Jun 23. PubMed PMID: 26075947.

18: Bergstrom DE, Brattesani AJ, Ogawa MK, Reddy PA, Schweickert MJ, Balzarini J, De Clercq E. Antiviral activity of C-5 substituted tubercidin analogues. J Med Chem. 1984 Mar;27(3):285-92. PubMed PMID: 6699874.

19: Aso T, Saito K, Suzuki A, Saito Y. Synthesis and photophysical properties of pyrene-labeled 3-deaza-2'-deoxyadenosines comprising a non-π-conjugated linker: fluorescence quenching-based oligodeoxynucleotide probes for thymine identification. Org Biomol Chem. 2015 Nov 14;13(42):10540-7. doi: 10.1039/c5ob01605c. Epub 2015 Sep 4. PubMed PMID: 26338764.

20: Rabin MS, Gottesman MM. High frequency of mutation to tubercidin resistance in CHO cells. Somatic Cell Genet. 1979 Sep;5(5):571-83. PubMed PMID: 294700.

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