Home / Articles / New inhibitors of \textit{Mycobacterium tuberculosis} growth based on modified pyrimidine nucleosides and their analogues

New inhibitors of \textit{Mycobacterium tuberculosis} growth based on modified pyrimidine nucleosides and their analogues

Èduard Renatovich Shmalenyuk 1
Èduard Renatovich Shmalenyuk
,  , 
Ludmila Aleksandrovna Alexandrova 1
Ludmila Aleksandrovna Alexandrova
1 Engelhardt Institute of Molecular Biology, Russian Academy of Sciences
10.1070/RC2013v082n09ABEH004404
Published 30 November 2012
Communication , Volume 82, Issue 9, 896-915
28
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Shmalenyuk È. R., Kochetkov S. N., Alexandrova L. A. New inhibitors of \textit{Mycobacterium tuberculosis} growth based on modified pyrimidine nucleosides and their analogues // Russian Chemical Reviews. 2013. Vol. 82. No. 9. pp. 896-915.
GOST all authors (up to 50)
Copy cite
Shmalenyuk È. R., Kochetkov S. N., Alexandrova L. A. New inhibitors of \textit{Mycobacterium tuberculosis} growth based on modified pyrimidine nucleosides and their analogues // Russian Chemical Reviews. 2013. Vol. 82. No. 9. pp. 896-915.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC2013v082n09ABEH004404
UR - https://rcr.colab.ws/publications/10.1070/RC2013v082n09ABEH004404
TI - New inhibitors of \textit{Mycobacterium tuberculosis} growth based on modified pyrimidine nucleosides and their analogues
T2 - Russian Chemical Reviews
AU - Shmalenyuk, Èduard Renatovich
AU - Kochetkov, Sergei Nikolaevich
AU - Alexandrova, Ludmila Aleksandrovna
PY - 2013
DA - 2012/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 896-915
IS - 9
VL - 82
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2013_Shmalenyuk,
author = {Èduard Renatovich Shmalenyuk and Sergei Nikolaevich Kochetkov and Ludmila Aleksandrovna Alexandrova},
title = {New inhibitors of \textit{Mycobacterium tuberculosis} growth based on modified pyrimidine nucleosides and their analogues},
journal = {Russian Chemical Reviews},
year = {2013},
volume = {82},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2013v082n09ABEH004404},
number = {9},
pages = {896--915},
doi = {10.1070/RC2013v082n09ABEH004404}
}
MLA
Cite this
MLA
Copy cite
Shmalenyuk, Èduard Renatovich, et al. “New inhibitors of \textit{Mycobacterium tuberculosis} growth based on modified pyrimidine nucleosides and their analogues.” Russian Chemical Reviews, vol. 82, no. 9, Nov. 2013, pp. 896-915. https://rcr.colab.ws/publications/10.1070/RC2013v082n09ABEH004404.
Views / Visits / Downloads
23 / 23 / 11

Abstract

Data on the methods of synthesis and antituberculosis activities of pyrimidine nucleoside derivatives and their analogues are summarized. A number of enzymes, promising targets for the prototypes of a new generation of drugs, are considered. The nucleosides able to inhibit drug-resistant strains of \textit{M. tuberculosis} are characterized.

The bibliography includes 102 references.

References

1.
Ancient Origin and Gene Mosaicism of the Progenitor of Mycobacterium tuberculosis
Gutierrez M.C., Brisse S., Brosch R., Fabre M., Omaïs B., Marmiesse M., Supply P., Vincent V.
PLoS Pathogens , 2005
2.
Isoniazid prophylaxis for tuberculosis in HIV infection: a meta-analysis of randomized controlled trials.
Bucher H.C., Griffith L.E., Guyatt G.H., Sudre P., Naef M., Sendi P., Battegay M.
AIDS , 2003
3.
An outbreak of tuberculosis with accelerated progression among persons infected with the human immunodeficiency virus. An analysis using restriction-fragment-length polymorphisms.
Daley C.L., Small P.M., Schecter G.F., Schoolnik G.K., McAdam R.A., Jacobs W.R., Hopewell P.C.
New England Journal of Medicine , 1992
4.
Efficacy of BCG Vaccine in the Prevention of Tuberculosis
Colditz G.A.
JAMA - Journal of the American Medical Association , 1994
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
The magic bullets and tuberculosis drug targets.
Zhang Y.
Annual Review of Pharmacology and Toxicology , 2005
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
Natural Products as Leads for Tuberculosis Drug Development
E. Salomon C., E. Schmidt L.
Current Topics in Medicinal Chemistry , 2012
10.
Novel Agents in the Management of Mycobacterium Tuberculosis Disease
P.J. Barry, T.M. O'Connor
Current Medicinal Chemistry , 2007
11.
Tuberculosis: The drug development pipeline at a glance
Villemagne B., Crauste C., Flipo M., Baulard A.R., Déprez B., Willand N.
European Journal of Medicinal Chemistry , 2012
12.
New Antituberculous Drugs in Development
Lalloo U.G., Ambaram A.
Current HIV/AIDS Reports , 2010
14.
Adenylating enzymes in Mycobacterium tuberculosis as drug targets.
P. Duckworth B., M. Nelson K., C. Aldrich C.
Current Topics in Medicinal Chemistry , 2012
15.
Development of a selective activity-based probe for adenylating enzymes: profiling MbtA Involved in siderophore biosynthesis from Mycobacterium tuberculosis.
Duckworth B.P., Wilson D.J., Nelson K.M., Boshoff H.I., Barry C.E., Aldrich C.C.
ACS Chemical Biology , 2012
16.
Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria.
Rai D., Johar M., Manning T., Agrawal B., Kunimoto D.Y., Kumar R.
Journal of Medicinal Chemistry , 2005
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
22.
Inhibition of Mycobacterium tuberculosis, Mycobacterium bovis, and Mycobacterium avium by novel dideoxy nucleosides.
Rai D., Johar M., Srivastav N.C., Manning T., Agrawal B., Kunimoto D.Y., Kumar R.
Journal of Medicinal Chemistry , 2007
23.
Use of Lawesson's Reagent in Organic Syntheses
Ozturk T., Ertas E., Mert O.
Chemical Reviews , 2007
25.
Synthesis and antitumor and antiviral properties of 5-alkyl-2'-deoxyuridines 3',5'-cyclic monophosphates, and neutral cyclic triesters
Beres J., Bentrude W.G., Balzarini J., De Clercq E., Otvos L.
Journal of Medicinal Chemistry , 1986
27.
Pharmacokinetics of netivudine, a potent anti-varicella zoster virus drug, in patients with renal impairment
Fillastre J.P., Godin M., Legallicier B., Chretien P., Bidault R., GillotiiT C., Wooton R., Posner J., Peck R.W.
Journal of Antimicrobial Chemotherapy , 1996
28.
3'-bromo analogues of pyrimidine nucleosides as a new class of potent inhibitors of Mycobacterium tuberculosis.
Shakya N., Srivastav N.C., Desroches N., Agrawal B., Kunimoto D.Y., Kumar R.
Journal of Medicinal Chemistry , 2010
29.
Antimycobacterial activities of 5-alkyl (or halo)-3′-substituted pyrimidine nucleoside analogs
Srivastav N.C., Shakya N., Bhavanam S., Agrawal A., Tse C., Desroches N., Kunimoto D.Y., Kumar R.
Bioorganic and Medicinal Chemistry Letters , 2012
33.
Toxicologic and antitumor studies on 5-hydroxymethyldeoxyuridine
Meldrum J.B., Gupta V.S., Lowes N.R., Paterson A.R.
Toxicology and Applied Pharmacology , 1985
34.
Alexandrova L.A., Shmalenyuk E.R., Kochetkov S.N., Erokhin V.V., Smirnova T.G., Andreevskaia S.N., Chernousova L.N.
Acta Naturae , 2010
35.
Inhibition of Mycobacterium tuberculosis strains H37Rv and MDR MS-115 by a new set of C5 modified pyrimidine nucleosides.
Shmalenyuk E.R., Chernousova L.N., Karpenko I.L., Kochetkov S.N., Smirnova T.G., Andreevskaya S.N., Chizhov A.O., Efremenkova O.V., Alexandrova L.A.
Bioorganic and Medicinal Chemistry , 2013
36.
36
J. Billon
Bull. Soc. chim. France , 1960
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
40.
Phosphoryl tris-triazole - a new phosphorylating reagent
Kraszewski A., Stawiński J.
Tetrahedron Letters , 1980
42.
Modification of nucleic acids using [3 + 2]-dipolar cycloaddition of azides and alkynes
Ustinov A.V., Stepanova I.A., Dubnyakova V.V., Zatsepin T.S., Nozhevnikova E.V., Korshun V.A.
Russian Journal of Bioorganic Chemistry , 2010
43.
A new solvent system for efficient synthesis of 1,2,3-triazoles
Lee B., Park S.R., Jeon H.B., Kim K.S.
Tetrahedron Letters , 2006
44.
Oligonucleotide derivatives bearing reactive and stabilizing groups attached to C5 of deoxyuridine
Levina A.S., Tabatadse D.R., Khalimskaya L.M., Prichodko T.A., Shishkin G.V., Alexandrova L.A., Zarytova V.P.
Bioconjugate Chemistry , 1993
45.
Studies on acyclic pyrimidines as inhibitors of mycobacteria.
Srivastav N.C., Manning T., Kunimoto D.Y., Kumar R.
Bioorganic and Medicinal Chemistry , 2007
46.
Acyclic nucleosides as antiviral compounds
Freeman S., Gardiner J.M.
Molecular Biotechnology , 1996
47.
Substrate specificity of Escherichia coli thymidine phosphorylase
Panova N.G., Alexeev C.S., Kuzmichov A.S., Shcheveleva E.V., Gavryushov S.A., Polyakov K.M., Kritzyn A.M., Mikhailov S.N., Esipov R.S., Miroshnikov A.I.
Biochemistry (Moscow) , 2007
48.
Mikhailopulo Igor Alexandrovich, Miroshnikov Anatoly Ivanovich
Mendeleev Communications , 2011
49.
Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.
Johar M., Manning T., Kunimoto D.Y., Kumar R.
Bioorganic and Medicinal Chemistry , 2005
50.
Chemistry and antiviral activities of acyclonucleosides
Chu C.K., Cutler S.J.
Journal of Heterocyclic Chemistry , 1986
53.
Carbocyclic nucleoside analogues: classification, target enzymes, mechanisms of action and synthesis
Matyugina E.S., Khandazhinskaya A.P., Kochetkov S.N.
Russian Chemical Reviews , 2012
54.
The synthesis and antituberculosis activity of 5'-nor carbocyclic uracil derivatives.
Matyugina E., Khandazhinskaya A., Chernousova L., Andreevskaya S., Smirnova T., Chizhov A., Karpenko I., Kochetkov S., Alexandrova L.
Bioorganic and Medicinal Chemistry , 2012
57.
Genes required for mycobacterial growth defined by high density mutagenesis
Sassetti C.M., Boyd D.H., Rubin E.J.
Molecular Microbiology , 2003
58.
Pyrimidine salvage pathway in Mycobacterium tuberculosis.
D. Villela A., A. Sanchez-Quitian Z., G. Ducati R., S. Santos D., A. Basso L.
Current Medicinal Chemistry , 2011
59.
Mycobacterium tuberculosis Thymidylate Kinase: Structural Studies of Intermediates along the Reaction Pathway
Fioravanti E., Haouz A., Ursby T., Munier-Lehmann H., Delarue M., Bourgeois D.
Journal of Molecular Biology , 2003
61.
Crystallization and preliminary X-ray analysis of the thymidylate kinase fromMycobacterium tuberculosis
Li de la Sierra I., Munier-Lehmann H., Gilles A.M., Bârzu O., Delarue M.
Acta Crystallographica Section D Biological Crystallography , 2000
62.
X-ray structure of TMP kinase from Mycobacterium tuberculosis complexed with TMP at 1.95 A resolution.
Li de la Sierra I., Munier-Lehmann H., Gilles A.M., Bârzu O., Delarue M.
Journal of Molecular Biology , 2001
63.
Enzymatic and Structural Analysis of Inhibitors Designed against Mycobacterium tuberculosis Thymidylate Kinase
Haouz A., Vanheusden V., Munier-Lehmann H., Froeyen M., Herdewijn P., Van Calenbergh S., Delarue M.
Journal of Biological Chemistry , 2003
64.
Insights into the phosphoryltransfer mechanism of human thymidylate kinase gained from crystal structures of enzyme complexes along the reaction coordinate
Ostermann N., Schlichting I., Brundiers R., Konrad M., Reinstein J., Veit T., Goody R.S., Lavie A.
Structure , 2000
65.
Structure of thymidylate kinase reveals the cause behind the limiting step in AZT activation
Lavie A., Vetter I.R., Konrad M., Goody R.S., Reinstein J., Schlichting I.
Nature Structural Biology , 1997
66.
Thymidine and thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase
Vanheusden V., Van Rompaey P., Munier-Lehmann H., Pochet S., Herdewijn P., Van Calenbergh S.
Bioorganic and Medicinal Chemistry Letters , 2003
67.
Discovery of Bicyclic Thymidine Analogues as Selective and High-Affinity Inhibitors of Mycobacterium tuberculosis Thymidine Monophosphate Kinase
Vanheusden V., Munier-Lehmann H., Froeyen M., Busson R., Rozenski J., Herdewijn P., Van Calenbergh S.
Journal of Medicinal Chemistry , 2004
68.
Synthesis and Biological Evaluation of Bicyclic Nucleosides as Inhibitors of M. tuberculosis Thymidylate Kinase
Van Daele I., Munier-Lehmann H., Hendrickx P. ., Marchal G., Chavarot P., Froeyen M., Qing L., Martins J., Van Calenbergh S.
ChemMedChem , 2006
69.
Rational Design of 5‘-Thiourea-Substituted α-Thymidine Analogues as Thymidine Monophosphate Kinase Inhibitors Capable of Inhibiting Mycobacterial Growth
Van Daele I., Munier-Lehmann H., Froeyen M., Balzarini J., Van Calenbergh S.
Journal of Medicinal Chemistry , 2007
70.
Unique Mechanism of Action of the Thiourea Drug Isoxyl on Mycobacterium tuberculosis
Phetsuksiri B., Jackson M., Scherman H., McNeil M., Besra G.S., Baulard A.R., Slayden R.A., DeBarber A.E., Barry C.E., Baird M.S., Crick D.C., Brennan P.J.
Journal of Biological Chemistry , 2003
71.
Urbancik B.
Antibiotica et chemotherapia. Fortschritte. Advances. Progres , 2022
72.
Synthesis of 2′,3′-dideoxy-3′-hydroxymethylcytidine; a unique antiviral nucleoside
Faul M.M., Huff B.E., Dunlap S.E., Frank S.A., Fritz J.E., Kaldor S.W., LeTourneau M.E., Staszak M.A., Ward J.A., Werner J.A., Winneroski L.L.
Tetrahedron , 1997
74.
Synthesis of pyrimidine 3'-allyl-2',3'-dideoxyribonucleosides by free-radical coupling
Chu C.K., Doboszewski B., Schmidt W., Ullas G.V., Van Roey P.
Journal of Organic Chemistry , 1989
76.
Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase
Van Poecke S., Munier-Lehmann H., Helynck O., Froeyen M., Van Calenbergh S.
Bioorganic and Medicinal Chemistry , 2011
77.
3'-[4-Aryl-(1,2,3-triazol-1-yl)]-3'-deoxythymidine analogues as potent and selective inhibitors of human mitochondrial thymidine kinase.
Van Poecke S., Negri A., Gago F., Van Daele I., Solaroli N., Karlsson A., Balzarini J., Van Calenbergh S.
Journal of Medicinal Chemistry , 2010
78.
Click Chemistry: Diverse Chemical Function from a Few Good Reactions
Kolb H.C., Finn M.G., Sharpless K.B.
Angewandte Chemie - International Edition , 2001
79.
Substituted benzyl-pyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: synthesis and in vitro anti-mycobacterial activity.
Gasse C., Douguet D., Huteau V., Marchal G., Munier-Lehmann H., Pochet S.
Bioorganic and Medicinal Chemistry , 2008
83.
Exploring Acyclic Nucleoside Analogues as Inhibitors of Mycobacterium tuberculosis Thymidylate Kinase
Familiar O., Munier‐Lehmann H., Negri A., Gago F., Douguet D., Rigouts L., Hernández A., Camarasa M., Pérez‐Pérez M.
ChemMedChem , 2008
85.
Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor
Walser A., Flynn T., Mason C., Crowley H., Maresca C., Yaremko B., O'Donnell M.
Journal of Medicinal Chemistry , 1991
86.
The catalytic mechanism and structure of thymidylate synthase.
Carreras C.W., Santi D.V.
Annual Review of Biochemistry , 1995
87.
An Alternative Flavin-Dependent Mechanism for Thymidylate Synthesis
Myllykallio H., Lipowski G., Leduc D., Filee J., Forterre P., Liebl U.
Science , 2002
88.
Structure of the Mycobacterium tuberculosis Flavin Dependent Thymidylate Synthase (MtbThyX) at 2.0Å Resolution
Sampathkumar P., Turley S., Ulmer J.E., Rhie H.G., Sibley C.H., Hol W.G.
Journal of Molecular Biology , 2005
90.
Functional Analysis of Substrate and Cofactor Complex Structures of a Thymidylate Synthase-Complementing Protein
Mathews I.I., Deacon A.M., Canaves J.M., McMullan D., Lesley S.A., Agarwalla S., Kuhn P.
Structure , 2003
91.
Synthesis and Evaluation of 5-Substituted 2′-deoxyuridine Monophosphate Analogues As Inhibitors of Flavin-Dependent Thymidylate Synthase in Mycobacterium tuberculosis
Kögler M., Vanderhoydonck B., De Jonghe S., Rozenski J., Van Belle K., Herman J., Louat T., Parchina A., Sibley C., Lescrinier E., Herdewijn P.
Journal of Medicinal Chemistry , 2011
92.
Studies of Phosphorylation. III. Selective Phosphorylation of Unprotected Nucleosides
Yoshikawa M., Kato T., Takenishi T.
Bulletin of the Chemical Society of Japan , 1969
94.
Selective phosphorylation of the 5'-hydroxy groups of thymidine and uridine
Mitsunobu O., Kato K., Kimura J.
Journal of the American Chemical Society , 1969
95.
2-Cyanoethyl Phosphate and its Use in the Synthesis of Phosphate Esters1
Tener G.M.
Journal of the American Chemical Society , 1961
98.
New 5-Substituted 6-Azauracils1
CHANG P.K.
Journal of Organic Chemistry , 1961