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 8297	7.5 µM [IC50]
DNA 278 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 8297	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 8297	530.0 nM [Ki]
DNA polymerase alpha subunit 9 Target ID: CHEMBL1828 Sources: https://www.ncbi.nlm.nih.gov/pubmed/750269	Inhibitor 8297

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 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7248975	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Binding thermodynamics of the transition state analogue coformycin and of the ground state analogue 1-deazaadenosine to bovine adenosine deaminase.	2001	11697042
Pre-analytical conditions affecting the determination of the plasma homocysteine concentration.	2001 Aug	11592432
Methionine depletion induces transcription of the mRNA (N6-adenosine)methyltransferase.	2001 Nov	11551827
Stabilization of blood homocysteine in an epidemiological setting.	2001 Oct	11711763
S-adenosyl-L-homocysteine hydrolase is necessary for aldosterone-induced activity of epithelial Na(+) channels.	2001 Sep	11502554
Recent developments in the discovery of novel adenosine kinase inhibitors: mechanism of action and therapeutic potential.	2001 Winter	11830758
Study on the synthesis and PKA-I binding activities of 5-alkynyl tubercidin analogues.	2002 Apr	11836097
Renal organic cation and nucleoside transport.	2002 Jul 15	12123738
Interaction of S-adenosylhomocysteine hydrolase of Xenopus laevis with mRNA(guanine-7-)methyltransferase: implication on its nuclear compartmentalisation and on cap methylation of hnRNA.	2002 Jun 12	12063172
Enhancement of cellular adenosine triphosphate levels in PC12 cells by extracellular adenosine.	2002 Mar	11913523
Disruption of choline methyl group donation for phosphatidylethanolamine methylation in hepatocarcinoma cells.	2002 May 10	11864970
Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model for HIV) and bovine BHV-1.	2002 Sep	12110319
Purine and deazapurine nucleosides: synthetic approaches, molecular modelling and biological activity.	2003 Mar	12620415
Physiological concentrations of divalent magnesium ion activate the serine/threonine specific protein kinase ERK2.	2003 Mar 18	12627962
Acadesine activates AMPK and induces apoptosis in B-cell chronic lymphocytic leukemia cells but not in T lymphocytes.	2003 May 1	12522004
Functional characterisation of nucleoside transport in rat brain endothelial cells.	2003 May 23	12802208
Quantitative structure-activity relationship study of 5-iodo- and diaryl-analogues of tubercidin: inhibitors of adenosine kinase.	2003 Oct	14692505
Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners.	2003 Sep	12919315
Phosphoramidate protides of carbocyclic 2',3'-dideoxy-2',3'-didehydro-7-deazaadenosine with potent activity against HIV and HBV.	2004	15628749
The S-adenosyl homocysteine hydrolase inhibitor 3-deaza-adenosine prevents oxidative damage and cognitive impairment following folate and vitamin E deprivation in a murine model of age-related, oxidative stress-induced neurodegeneration.	2004	15075443
Synthesis and biological activity of 5-fluorotubercidin.	2004	15043144
3-Deazaadenosine prevents leukocyte invasion by suppression of adhesion molecule expression during acute cardiac allograft rejection: involvement of apoptotic cell death.	2004 Aug	15312827
1,N6-Etheno derivative of 7-deaza-2,8-diazaadenosine.	2004 Aug	15295189
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.	2004 Jan	14645324
S-adenosylmethionine and its metabolite induce apoptosis in HepG2 cells: Role of protein phosphatase 1 and Bcl-x(S).	2004 Jul	15239106
3-Deazaadenosine analogues of p5'A2'p5'A2'p5'A: synthesis, stereochemistry, and the roles of adenine ring nitrogen-3 in the interaction with RNase L.	2004 Jul 1	15186848
Protein methylation activates reconstituted ryanodine receptor-ca release channels from coronary artery myocytes.	2004 May-Jun	15118362
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 Sep	15331515
Synthesis and biological evaluation of 2- and 7-substituted 9-deazaadenosine analogues.	2005	15715198
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Astrogliosis in epilepsy leads to overexpression of adenosine kinase, resulting in seizure aggravation.	2005 Oct	15930047
A pull-down assay for 5' AMP-activated protein kinase activity using the GST-fused protein.	2006 Jan	16382178
Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries.	2006 May	16556935
The role of adenosine in chondrocyte death in murine osteoarthritis and in a murine chondrocyte cell line.	2006 May	16443378
2-Amino-7-chloro-2'-deoxytubercidin.	2006 Oct	17008745
Biochemical and biological properties of 5-bromotubercidin: differential effects on cellular DNA-directed and viral RNA-directed RNA synthesis.	2008 Feb 1	17977728
3-Deazaadenosine inhibits vasa vasorum neovascularization in aortas of ApoE(-/-)/LDL(-/-) double knockout mice.	2009 Jan	18495128

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 `Fri Dec 15 15:09:54 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:54 GMT 2023`
Record UNII	M351LCX45Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TUBERCIDIN

Common Name

English

7-DEAZAADENOSINE

Common Name

English

TUBERCIDIN [MI]

Common Name

English

U-10071

Code

English

NSC-56408

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