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
Fluorescent DNA: the development of 7-deazapurine nucleoside triphosphates applicable for sequencing at the single molecule level.	2001 Apr 13	11257536
Analysis of increased leukocyte ratio induced by tumor necrosis factor-alpha using several inhibitors in the undisturbed microcirculation of the rat mesentery.	2001 Mar	11367539
Methionine depletion induces transcription of the mRNA (N6-adenosine)methyltransferase.	2001 Nov	11551827
Syntheses of puromycin from adenosine and 7-deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair.	2001 Nov 30	11722226
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
Identification of A-minor tertiary interactions within a bacterial group I intron active site by 3-deazaadenosine interference mapping.	2002 Aug 20	12173929
Kinetics of apoptotic markers in exogeneously induced apoptosis of EL4 cells.	2002 Jan-Mar	12003671
Renal organic cation and nucleoside transport.	2002 Jul 15	12123738
Effects of temperature on stability of blood homocysteine in collection tubes containing 3-deazaadenosine.	2002 Nov	12406988
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
Effect of hyperhomocysteinemia on plasma or tissue adenosine levels and renal function.	2002 Sep 3	12208805
Protective effect of 3-deazaadenosine in a rat model of lipopolysaccharide-induced myocardial dysfunction.	2003 Mar	12630524
Quantitative structure-activity relationship study of 5-iodo- and diaryl-analogues of tubercidin: inhibitors of adenosine kinase.	2003 Oct	14692505
Synthesis and biological activity of 5-fluorotubercidin.	2004	15043144
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
Overexpression of adenosine kinase in epileptic hippocampus contributes to epileptogenesis.	2004 Jan 21	14736855
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
Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.	2005 Apr 22	15701636
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
Antiviral properties of deazaadenine nucleoside derivatives.	2006	17168721
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 Apr	16598151
3-Deazaadenosine mitigates arterial remodeling and hypertension in hyperhomocysteinemic mice.	2006 Nov	16815886
Threonine phosphorylation of integrin beta3 in calyculin A-treated platelets is selectively sensitive to 5'-iodotubercidin.	2007 Feb	17052767
Transgenic overexpression of adenosine kinase aggravates cell death in ischemia.	2007 Jan	16685255
Role of the stage-regulated nucleoside transporter TbNT10 in differentiation and adenosine uptake in Trypanosoma brucei.	2007 Jul	17521750
TOR-induced resistance to toxic adenosine analogs in Leishmania brought about by the internalization and degradation of the adenosine permease.	2007 May 15	17428463
The 7-bromo derivative of 2-amino-2'-deoxytubercidin fluorinated at the sugar moiety.	2007 Oct	17917233
Biochemical and biological properties of 5-bromotubercidin: differential effects on cellular DNA-directed and viral RNA-directed RNA synthesis.	2008 Feb 1	17977728
7-deazainosine derivatives: synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides.	2008 May	18569790

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