TUBERCIDIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H14N4O4
Molecular Weight	266.2533
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HDZZVAMISRMYHH-KCGFPETGSA-N

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

HIDE SMILES / InChI

Molecular Formula	C11H14N4O4
Molecular Weight	266.2533
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2764531 | https://www.ncbi.nlm.nih.gov/pubmed/750269 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C911

Tubercidin, an adenosine analogue, is a nucleoside antibiotic. It is incorporated into DNA and inhibits polymerases, thereby inhibiting DNA replication and RNA and protein synthesis. This agent also exhibits antifungal and antiviral activities.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phosphoglycerate kinase 1 Target ID: CHEMBL2362982 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12972414	Inhibitor 8504	7.5 µM [IC50]
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9540207 \| https://www.ncbi.nlm.nih.gov/pubmed/750269	Interacts 323
Adenosine kinase 2 Target ID: CHEMBL2384 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2986372	Inhibitor 8504	1.9 µM [Ki]
MAP kinase ERK2 7 Target ID: CHEMBL4040 Sources: https://books.google.ru/books?id=fMItDwAAQBAJ&pg=RA5-PA2030&lpg=RA5-PA2030&dq=TUBERCIDIN retrieved from The Inhibitor Index : A Desk Reference on Enzyme Inhibitors, Receptor Antagonists, Drugs, Toxins, Poisons, Biologics, and Therapeutic Leads, p.2031	Inhibitor 8504	530.0 nM [Ki]
DNA polymerase alpha subunit 9 Target ID: CHEMBL1828 Sources: https://www.ncbi.nlm.nih.gov/pubmed/750269	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schistosomiasis 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1900158	Primary		Preclinical	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7248975	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Overexpression of CYP2E1 induces HepG2 cells death by the AMP kinase activator 5'-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside (AICAR).	2009-06	18473182
A small molecule inhibitor of alpha4 integrin-dependent cell migration.	2009-02-01	18329275
3-Deazaadenosine inhibits vasa vasorum neovascularization in aortas of ApoE(-/-)/LDL(-/-) double knockout mice.	2009-01	18495128
Conformational change of adenosine deaminase during ligand-exchange in a crystal.	2008-08-15	18549808
[Conformation of adenosine deaminase in complexes with inhibitors: application of selective quenching of fluorescence emission].	2008-06-12	18543763
7-deazainosine derivatives: synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides.	2008-05	18569790
7-Fluorotubercidin: a halogenated derivative of a naturally occurring nucleoside antimetabolite.	2008-05	18451491
Adenosine actions are preserved in corpus cavernosum from obese and type II diabetic db/db mouse.	2008-05	18221284
Biochemical and biological properties of 5-bromotubercidin: differential effects on cellular DNA-directed and viral RNA-directed RNA synthesis.	2008-02-01	17977728
Cystathionine-beta-synthase gene transfer and 3-deazaadenosine ameliorate inflammatory response in endothelial cells.	2007-12	17855772
Synthesis and antimicrobial activity of some novel nucleoside analogues of adenosine and 1,3-dideazaadenosine.	2007-11-15	17890082
The 7-bromo derivative of 2-amino-2'-deoxytubercidin fluorinated at the sugar moiety.	2007-10	17917233
Long-term administration of 3-deazaadenosine does not alter progression of advanced atherosclerotic lesions in apolipoprotein E-deficient mice.	2007-08	17703138
Cytotoxic effect of 5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside (AICAR) on childhood acute lymphoblastic leukemia (ALL) cells: implication for targeted therapy.	2007-07-10	17623090
Extended storage of whole blood with 3-deazaadenosine for homocysteine assay.	2007-07	17594787
Role of the stage-regulated nucleoside transporter TbNT10 in differentiation and adenosine uptake in Trypanosoma brucei.	2007-07	17521750
Genome-wide fitness test and mechanism-of-action studies of inhibitory compounds in Candida albicans.	2007-06	17604452
TOR-induced resistance to toxic adenosine analogs in Leishmania brought about by the internalization and degradation of the adenosine permease.	2007-05-15	17428463
A dengue fever viremia model in mice shows reduction in viral replication and suppression of the inflammatory response after treatment with antiviral drugs.	2007-03-01	17262707
Threonine phosphorylation of integrin beta3 in calyculin A-treated platelets is selectively sensitive to 5'-iodotubercidin.	2007-02	17052767
Membrane localization and pH-dependent transport of a newly cloned organic cation transporter (PMAT) in kidney cells.	2007-02	17018840
Evaluation of 3-deaza-adenosine analogues as ligands for adenosine kinase and inhibitors of Mycobacterium tuberculosis growth.	2007-01	17085766
Transgenic overexpression of adenosine kinase aggravates cell death in ischemia.	2007-01	16685255
Characterization of copper(II) interactions with sinefungin, a nucleoside antibiotic: combined potentiometric, spectroscopic and DFT studies.	2007	18273386
Functional characterization of nucleoside transporter gene replacements in Leishmania donovani.	2006-12	17050001
Crystal structures of human adenosine kinase inhibitor complexes reveal two distinct binding modes.	2006-11-16	17154503
3-Deazaadenosine mitigates arterial remodeling and hypertension in hyperhomocysteinemic mice.	2006-11	16815886
2-Amino-7-chloro-2'-deoxytubercidin.	2006-10	17008745
Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries.	2006-05	16556935
AMP-dependent protein kinase alpha 2 isoform promotes hypoxia-induced VEGF expression in human glioblastoma.	2006-05	16518831
The role of adenosine in chondrocyte death in murine osteoarthritis and in a murine chondrocyte cell line.	2006-05	16443378
4-Amino-7-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine: a bis-fluorinated analogue of 2'-deoxytubercidin.	2006-04	16598151
A pull-down assay for 5' AMP-activated protein kinase activity using the GST-fused protein.	2006-01	16382178
Antiviral properties of deazaadenine nucleoside derivatives.	2006	17168721
Adenosine kinase inhibitors. 5. Synthesis, enzyme inhibition, and analgesic activity of diaryl-erythro-furanosyltubercidin analogues.	2005-10-06	16190769
Astrogliosis in epilepsy leads to overexpression of adenosine kinase, resulting in seizure aggravation.	2005-10	15930047
Molecular pharmacology of adenosine transport in Trypanosoma brucei: P1/P2 revisited.	2005-09	15933219
Mutational analysis of a nucleosidase involved in quorum-sensing autoinducer-2 biosynthesis.	2005-08-23	16101288
Inhibition of transmethylation disturbs neurulation in chick embryos.	2005-08-08	15996755
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.	2005-04-22	15701636
Inhibition of adenosine kinase attenuates interleukin-1- and lipopolysaccharide-induced alterations in articular cartilage metabolism.	2005-03	15727892
Synthesis and biological evaluation of 2- and 7-substituted 9-deazaadenosine analogues.	2005	15715198
3-Deazaadenosine, a stabilizer of whole-blood homocysteine content, does not interfere with the single-enzyme homocysteine assay while totally inhibiting the enzyme conversion homocysteine immunoassay.	2004-09	15331515
3-Deazaadenosine prevents leukocyte invasion by suppression of adhesion molecule expression during acute cardiac allograft rejection: involvement of apoptotic cell death.	2004-08	15312827
1,N6-Etheno derivative of 7-deaza-2,8-diazaadenosine.	2004-08	15295189
S-adenosylmethionine and its metabolite induce apoptosis in HepG2 cells: Role of protein phosphatase 1 and Bcl-x(S).	2004-07	15239106
Dietary supplementation with 3-deaza adenosine, N-acetyl cysteine, and S-adenosyl methionine provide neuroprotection against multiple consequences of vitamin deficiency and oxidative challenge: relevance to age-related neurodegeneration.	2004	15970627
Phosphoramidate protides of carbocyclic 2',3'-dideoxy-2',3'-didehydro-7-deazaadenosine with potent activity against HIV and HBV.	2004	15628749
Design, synthesis, and studies on the structure activity relationships of certain pyrrolo[2,3-d]pyrimidine nucleosides and structurally related analogs as potential antineoplastic and antiviral agents.	1991-01	1649609

Patents

Sample Use Guides

In Vivo Use Guide

HaM/ICR females mice (20 to 25 g), infected with from 3 to 5 Fasciola hepatica metacercariae per os, were treated with a single dose of thepurine nucleoside analog tubercidin (7-deaza-adenosine; Tu) 7, 14, 21, and 28 days postexposure.Tu was administered either by direct intravenous injection or intraerythrocytically. The minimal single intravenous dose of Tu that was maximally effective was between 10 and 20 mg/kg.

Route of Administration: Intravenous

In Vitro Use Guide

Short (1-h) exposures to 1 uM tubercidin alone inhibited colony formation (a) of normal human hematopoietic progenitors (CFU-GEMM, BFU-E, CFU-GM) by 100%, and (b) of HL-60/C1 and CCRF-CEM cells by > 90%. Pretreatment (30 min) followed by simultaneous treatment (1 h) with any of the transport inhibitors (> or = 0.1 uM) and 0.1 uM [3H]-tubercidin blocked the uptake of radioactivity completely in CCRF-CEM cells and only partially in HL-60/C1 cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:40 GMT 2025`
Record UNII	M351LCX45Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TUBERCIDIN

Common Name

English

NSC-56408

Preferred Name

English

7-DEAZAADENOSINE

Common Name

English

TUBERCIDIN [MI]

Common Name

English

U-10071

Code

English

7-.BETA.-D-RIBOFURANOSYL-7H-PYRROLO(2,3-D)PYRIMIDIN-4-AMINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1556