{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T10:24:36Z","timestamp":1787653476406,"version":"build-2736575974"},"reference-count":46,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T00:00:00Z","timestamp":1787529600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["25-14-00305"],"award-info":[{"award-number":["25-14-00305"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["24-14-00458"],"award-info":[{"award-number":["24-14-00458"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]},{"award":["25-14-00305"],"award-info":[{"award-number":["25-14-00305"]}],"id":[{"id":"https:\/\/ror.org\/03y2gwe85","id-type":"ROR","asserted-by":"publisher"}]},{"award":["24-14-00458"],"award-info":[{"award-number":["24-14-00458"]}],"id":[{"id":"https:\/\/ror.org\/03y2gwe85","id-type":"ROR","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Int. J. Mol. Sci.","IJMS"],"abstract":"<jats:p>New indazole and pyrazole nucleoside analogues were synthesized by enzymatic transglycosylation using E. coli purine nucleoside phosphorylase (PNP). Indazoles substituted at position 5 or 6 with bromine, pyrazole or pyrimidine fragments were used as heterocyclic bases. In the case of indazole-pyrazole hybrids, the selectivity of PNP in glycosylation of the pyrazole fragment, rather than the indazole one, was established. Molecular modeling methods allowed the identification of the preferred orientations of substrates in the active site of the enzyme, leading to the formation of N1- and N2-regioisomers of indazole. Unique substrate specificity ensured the possibility of glycosylation of the bases with conversion rates of 65\u2013100% (according to HPLC analysis of the reaction mixtures) and isolated yields of 19\u201394%. It was shown that the synthesized nucleoside analogues are not inhibitors of E. coli adenosine deaminase (ADA). They do not exhibit cytotoxicity towards cancer cell lines (SH-SY5Y neuroblastoma cell lines, K-562 lymphoblastic cells, and HL-60 promyeloblastic cells). The activity of indazole derivatives against Mycobacterium tuberculosis (strain H37Rv) was determined by the microdilution method. 1-(\u03b2-D-2\u2032deoxyribofuranosyl)-5-bromo-indazole and 5-(pyrimidin-5-yl)-1H-indazole at a concentration of 50 \u03bcg\/mL were able to inhibit 50% and 90% of the culture growth, correspondingly.<\/jats:p>","DOI":"10.3390\/ijms27177551","type":"journal-article","created":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T11:47:19Z","timestamp":1787572039000},"page":"7551","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Exploring Novel Indazole and Pyrazole Nucleoside Analogues: Enzymatic Synthesis, Characterization, and Biological Evaluation"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-8943-6918","authenticated-orcid":false,"given":"Anton F.","family":"Mironov","sequence":"first","affiliation":[{"name":"Shemyakin-Ovchinnikov Institute 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Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0930-5604","authenticated-orcid":false,"given":"Vera A.","family":"Sokhraneva","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov St. 32, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Iulia S.","family":"Zhivotova","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov St. 32, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7443-6961","authenticated-orcid":false,"given":"Sergey N.","family":"Kochetkov","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov St. 32, 119991 Moscow, 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Palacios-Espinosa, J.F., Cort\u00e9s-Ben\u00edtez, F., Leyte-Lugo, M., Varela-Petrissans, B., and Quintana-Salazar, E.A. (2021). Design, Synthesis and Anticandidal Evaluation of Indazole and Pyrazole Derivatives. Pharmaceuticals, 14.","DOI":"10.3390\/ph14030176"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"5196","DOI":"10.1039\/D5MD00336A","article-title":"Indazole\u2014An Emerging Privileged Scaffold: Synthesis and Its Biological Significance","volume":"16","author":"Singampalli","year":"2025","journal-title":"RSC Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1007\/s41061-025-00509-9","article-title":"Recent Advances in Synthetic Strategies and Biological Properties of Indazole Scaffolds: A Review","volume":"383","author":"Boddapati","year":"2025","journal-title":"Top. Curr. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1517\/14740338.2012.712108","article-title":"Safety and Tolerability of Pazopanib in the Treatment of Renal Cell Carcinoma","volume":"11","author":"Zivi","year":"2012","journal-title":"Expert Opin. Drug Saf."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1029","DOI":"10.1007\/s40265-017-0752-y","article-title":"Niraparib: First Global Approval","volume":"77","author":"Scott","year":"2017","journal-title":"Drugs"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"296","DOI":"10.1111\/j.1476-5381.1993.tb12798.x","article-title":"7-Nitro Indazole, an Inhibitor of Nitric Oxide Synthase, Exhibits Anti-Nociceptive Activity in the Mouse without Increasing Blood Pressure","volume":"108","author":"Moore","year":"1993","journal-title":"Br. J. Pharmacol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"6180","DOI":"10.1016\/j.bmc.2009.07.067","article-title":"Fluorinated Indazoles as Novel Selective Inhibitors of Nitric Oxide Synthase (NOS): Synthesis and Biological Evaluation","volume":"17","author":"Claramunt","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1152","DOI":"10.2174\/1568026622666220512145646","article-title":"Impact of Indazole Scaffold as Antibacterial and Antifungal Agent","volume":"22","author":"Nanda","year":"2022","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1021","DOI":"10.2174\/0109298673389070250822065247","article-title":"New Indazole Derivatives as Potential Scaffolds for the Development of Anticancer, Antiviral, and Anti-Tuberculosis Chemotherapeutic Compounds","volume":"33","author":"Khandazhinskaya","year":"2025","journal-title":"Curr. Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Burke, A., Di Filippo, M., Spiccio, S., Schito, A.M., Caviglia, D., Brullo, C., and Baumann, M. (2023). Antimicrobial Evaluation of New Pyrazoles, Indazoles and Pyrazolines Prepared in Continuous Flow Mode. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24065319"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y.N., Al-aizari, F.A., and Ansar, M. (2018). Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review. Molecules, 23.","DOI":"10.3390\/molecules23010134"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"106599","DOI":"10.1016\/j.biocel.2024.106599","article-title":"Pyrazoles Have a Multifaceted Anti-Inflammatory Effect Targeting Prostaglandin E2, Cyclooxygenases and Leukocytes\u2019 Oxidative Burst","volume":"172","author":"Rocha","year":"2024","journal-title":"Int. J. Biochem. Cell Biol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"790","DOI":"10.1016\/j.ejmech.2015.07.031","article-title":"Design, Synthesis and Biological Evaluation of 1,3-Diphenyl-1H-Pyrazole Derivatives Containing Benzimidazole Skeleton as Potential Anticancer and Apoptosis Inducing Agents","volume":"101","author":"Reddy","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"343","DOI":"10.4155\/fmc-2021-0275","article-title":"Antibacterial Pyrazoles: Tackling Resistant Bacteria","volume":"14","author":"Alam","year":"2022","journal-title":"Future Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"103470","DOI":"10.1016\/j.bioorg.2019.103470","article-title":"Overview of Recent Developments of Pyrazole Derivatives as an Anticancer Agent in Different Cell Line","volume":"97","author":"Bennani","year":"2020","journal-title":"Bioorg. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"953","DOI":"10.2217\/fon-2018-0468","article-title":"Nilotinib in the Treatment of Chronic Myeloid Leukemia","volume":"15","author":"Sacha","year":"2018","journal-title":"Future Oncol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1080\/01902140701634827","article-title":"Imatinib mesylate inhibits fibrogenesis in asbestos-induced interstitial pneumonia","volume":"33","author":"Vuorinen","year":"2007","journal-title":"Exp. Lung Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1186\/s13014-021-01955-7","article-title":"Therapeutic Effect of Osimertinib plus Cranial Radiotherapy Compared to Osimertinib Alone in NSCLC Patients with EGFR-Activating Mutations and Brain Metastases: A Retrospective Study","volume":"16","author":"Zhai","year":"2021","journal-title":"Radiat. Oncol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"660","DOI":"10.1002\/psp4.13114","article-title":"Understanding CYP3A4 and P-gp Mediated Drug\u2013Drug Interactions through PBPK Modeling\u2013Case Example of Pralsetinib","volume":"13","author":"Bowman","year":"2024","journal-title":"CPT Pharmacomet. Syst. Pharmacol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2872","DOI":"10.1128\/AAC.01695-10","article-title":"Connection Domain Mutations in HIV-1 Reverse Transcriptase Do Not Impact Etravirine Susceptibility and Virologic Responses to Etravirine-Containing Regimens","volume":"55","author":"Gupta","year":"2011","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1002\/ccr3.254","article-title":"HIV Drug Resistance Mutations Following Poor Adherence in HIV-Infected Patient: A Case Report","volume":"3","author":"Masikini","year":"2015","journal-title":"Clin. Case Rep."},{"key":"ref_22","first-page":"54","article-title":"Trimethoprim-Resistant Enterobacteriaceae in Urinary Tract Infection","volume":"112","author":"Wong","year":"1975","journal-title":"Can. Med. Assoc. J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2834","DOI":"10.1128\/AAC.01383-08","article-title":"Multicenter, Randomized Study of the Efficacy and Safety of Intravenous Iclaprim in Complicated Skin and Skin Structure Infections","volume":"53","author":"Krievins","year":"2009","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1002\/ana.25950","article-title":"A Transcriptome-Based Drug Discovery Paradigm for Neurodevelopmental Disorders","volume":"89","author":"Dhindsa","year":"2021","journal-title":"Ann. Neurol."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Perrone, D., Marchesi, E., Preti, L., and Navacchia, M.L. (2021). Modified Nucleosides, Nucleotides and Nucleic Acids via Click Azide-Alkyne Cycloaddition for Pharmacological Applications. Molecules, 26.","DOI":"10.3390\/molecules26113100"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"599","DOI":"10.1080\/07328318908054201","article-title":"Nucleosides, XLIV1 Synthesis, Properties and Biological Activity of Indazole Nucleosides","volume":"8","author":"Kazimierczuk","year":"1989","journal-title":"Nucleosides Nucleotides Nucleotides Acids"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1002\/hlca.19910740209","article-title":"Stereoselective Synthesis of Indazole 2\u2032-Deoxy-\u03b2-D-ribonucleosides: Glycosylation of the Nucleobase Anion","volume":"74","author":"Seela","year":"1991","journal-title":"Helv. Chim. Acta"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1081\/NCN-120027830","article-title":"Regioselective Synthesis of Indazole N1- and N2-(Beta-D-Ribonucleosides)","volume":"23","author":"Seela","year":"2004","journal-title":"Nucleosides Nucleotides Nucleotides Acids"},{"key":"ref_29","first-page":"1","article-title":"ChemInform Abstract: The Synthesis and Reactions of Pyrrole, Pyrazole, Triazole, Indole, Indazole, and Benzotriazole Nucleosides and Nucleotides","volume":"3","author":"Preobrazhenskaya","year":"1995","journal-title":"ChemInform"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1412","DOI":"10.1002\/cbic.201900714","article-title":"An Expedient Synthesis of Flexible Nucleosides through Enzymatic Glycosylation of Proximal and Distal Fleximer Bases","volume":"21","author":"Ku","year":"2020","journal-title":"Chembiochem"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"7379","DOI":"10.1039\/D1OB01069G","article-title":"Novel Fleximer Pyrazole-Containing Adenosine Analogues: Chemical, Enzymatic and Highly Efficient Biotechnological Synthesis","volume":"19","author":"Khandazhinskaya","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1006\/prep.2001.1524","article-title":"Overexpression of Escherichia Coli Genes Encoding Nucleoside Phosphorylases in the pET\/Bl21(DE3) System Yields Active Recombinant Enzymes","volume":"24","author":"Esipov","year":"2002","journal-title":"Protein Expr. Purif."},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Khandazhinskaya, A., Eletskaya, B., Mironov, A., Konstantinova, I., Efremenkova, O., Andreevskaya, S., Smirnova, T., Chernousova, L., Kondrashova, E., and Chizhov, A. (2023). New Flexible Analogues of 8-Aza-7-Deazapurine Nucleosides as Potential Antibacterial Agents. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms242015421"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Eletskaya, B.Z., Mironov, A.F., Fateev, I.V., Berzina, M.Y., Antonov, K.V., Smirnova, O.S., Zatsepina, A.B., Arnautova, A.O., Abramchik, Y.A., and Paramonov, A.S. (2024). Enzymatic Transglycosylation Features in Synthesis of 8-Aza-7-Deazapurine Fleximer Nucleosides by Recombinant E. Coli PNP: Synthesis and Structure Determination of Minor Products. Biomolecules, 14.","DOI":"10.3390\/biom14070798"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3638","DOI":"10.1039\/C6OB00405A","article-title":"Expedient and Generic Synthesis of Imidazole Nucleosides by Enzymatic Transglycosylation","volume":"14","author":"Bonhomme","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Stachelska-Wierzchowska, A., Wierzchowski, J., G\u00f3rka, M., Bzowska, A., Stolarski, R., and Wielgus-Kutrowska, B. (2020). Tricyclic Nucleobase Analogs and Their Ribosides as Substrates and Inhibitors of Purine-Nucleoside Phosphorylases III. Aminopurine Derivatives. Molecules, 25.","DOI":"10.3390\/molecules25030681"},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Stachelska-Wierzchowska, A., and Wierzchowski, J. (2024). Chemo-Enzymatic Generation of Highly Fluorescent Nucleoside Analogs Using Purine-Nucleoside Phosphorylase. Biomolecules, 14.","DOI":"10.20944\/preprints202405.0891.v1"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.jinorgbio.2012.04.001","article-title":"Osmium(IV) Complexes with 1H- and 2H-Indazoles: Tautomer Identity versus Spectroscopic Properties and Antiproliferative Activity","volume":"113","author":"Stepanenko","year":"2012","journal-title":"J. Inorg. Biochem."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Arnautova, A.O., Aleksakhina, I.A., Zorina, E.A., Berzina, M.Y., Fateev, I.V., Eletskaya, B.Z., Antonov, K.V., Smirnova, O.S., Paramonov, A.S., and Kayushin, A.L. (2025). New Benzimidazole 3\u2019-Deoxynucleosides: Synthesis and Antiherpes Virus Properties. Biomolecules, 15.","DOI":"10.3390\/biom15070922"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"13401","DOI":"10.1002\/chem.201501334","article-title":"Recognition of Artificial Nucleobases by E. Coli Purine Nucleoside Phosphorylase versus Its Ser90Ala Mutant in the Synthesis of Base-Modified Nucleosides","volume":"21","author":"Fateev","year":"2015","journal-title":"Chemistry"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"109","DOI":"10.4103\/0970-2113.44121","article-title":"Adenosine Deaminase (ADA) Level in Tubercular Pleural Effusion","volume":"25","author":"Verma","year":"2008","journal-title":"Lung India"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Kutryb-Zajac, B., Mierzejewska, P., Slominska, E.M., and Smolenski, R.T. (2020). Therapeutic Perspectives of Adenosine Deaminase Inhibition in Cardiovascular Diseases. Molecules, 25.","DOI":"10.3390\/molecules25204652"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"605","DOI":"10.1111\/cbdd.13458","article-title":"Enzymatic Synthesis of Novel Purine Nucleosides Bearing a Chiral Benzoxazine Fragment","volume":"93","author":"Eletskaya","year":"2019","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"132","DOI":"10.1002\/(SICI)1096-987X(20000130)21:2<132::AID-JCC5>3.0.CO;2-P","article-title":"Fast, Efficient Generation of High-Quality Atomic Charges. AM1-BCC Model: I. Method","volume":"21","author":"Jakalian","year":"2000","journal-title":"J. Comput. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1107\/S2053230X18006337","article-title":"Crystal Structure of Escherichia Coli Purine Nucleoside Phosphorylase in Complex with 7-Deazahypoxanthine","volume":"74","author":"Timofeev","year":"2018","journal-title":"Acta Crystallogr. Sect. F. Struct. Biol. Commun."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1605","DOI":"10.1002\/jcc.20084","article-title":"UCSF Chimera\u2014A Visualization System for Exploratory Research and Analysis","volume":"25","author":"Pettersen","year":"2004","journal-title":"J. Comput. Chem."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/27\/17\/7551\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T10:05:31Z","timestamp":1787652331000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/27\/17\/7551"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,24]]},"references-count":46,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2026,9]]}},"alternative-id":["ijms27177551"],"URL":"https:\/\/doi.org\/10.3390\/ijms27177551","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,24]]}}}