دورية أكاديمية

Antiviral potency of lupane and oleanane alkynyl-derivatives against human cytomegalovirus and papillomavirus.

التفاصيل البيبلوغرافية
العنوان: Antiviral potency of lupane and oleanane alkynyl-derivatives against human cytomegalovirus and papillomavirus.
المؤلفون: Khusnutdinova EF; Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71 Prospect Oktyabrya, 450054, Ufa, Russian Federation. elmaH@inbox.ru., Petrova AV; Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71 Prospect Oktyabrya, 450054, Ufa, Russian Federation., Kazakova OB; Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71 Prospect Oktyabrya, 450054, Ufa, Russian Federation.
المصدر: The Journal of antibiotics [J Antibiot (Tokyo)] 2024 Jan; Vol. 77 (1), pp. 50-56. Date of Electronic Publication: 2023 Nov 07.
نوع المنشور: Journal Article; Research Support, N.I.H., Extramural
اللغة: English
بيانات الدورية: Publisher: Nature Publishing Group Country of Publication: England NLM ID: 0151115 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1881-1469 (Electronic) Linking ISSN: 00218820 NLM ISO Abbreviation: J Antibiot (Tokyo) Subsets: MEDLINE
أسماء مطبوعة: Publication: 2009- : London : Nature Publishing Group
Original Publication: Tokyo, Japan Antibiotics Research Assn.
مواضيع طبية MeSH: Oleanolic Acid*/pharmacology , Triterpenes*/pharmacology, Humans ; Cytomegalovirus ; Antiviral Agents/pharmacology ; Lupanes
مستخلص: A library of 18 structurally diverse semisynthetic lupane, oleanane, and ursane types triterpenoids, including C19- or C28-(1,2,3-triazolyl)- and aminomethylated derivatives obtained by the «click» reaction with various aromatic and sugar azides or by Mannich reaction with secondary amines, were tested for antiviral activity against HCMV, HSV-1, and HPV-11 types. C28-Triazolyl-derivative with a benzyl substituent of 2,3-indolo-oleanolic acid was the most active against the HCMV virus with EC 50  < 0.05 (SI > 81). Lupane 3,28-diacetoxy-triazolyl derivatives with phenyl- and fluorophenyl-fragments possess the highest activity among all screened compounds toward HPV-11 type virus with EC 50 values of 2.97 µM and 1.20 μM, SI 90 values of 28 and >125, respectively. One can see that modification of triterpenic alkynes to Mannich bases was more efficient in increasing an activity against HSV-1 than their conversion to triazoles.
(© 2023. The Author(s), under exclusive licence to the Japan Antibiotics Research Association.)
References: Dzubak P, Hajduch M, Vydra D, Hustova A, Kvasnica M, Biedermann D, Markova L, Urban M, Sarek J. Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat Prod Rep. 2006;23:394–411. https://doi.org/10.1039/b515312n . (PMID: 10.1039/b515312n16741586)
Salvador JAR, Leal AS, Valdeira AS, Gonçalves BMF, Alho DPS, Figueiredo SAC, Silvestre SM, Mendes VIS. Oleanane-, ursane-, and quinone methide friedelane-type triterpenoid derivatives: recent advances in cancer treatment. Eur J Med Chem. 2017;142:95–130. https://doi.org/10.1016/j.ejmech.2017.07.013 . (PMID: 10.1016/j.ejmech.2017.07.01328754470)
Isah MB, Ibrahim MA, Mohammed A, Aliyu AB, Masola B, Coetzer TH. A systematic review of pentacyclic triterpenes and their derivatives as chemotherapeutic agents against tropical parasitic diseases. Parasitology. 2016;143:1219–31. https://doi.org/10.1017/S0031182016000718 . (PMID: 10.1017/S003118201600071827240847)
Martin DE, Salzwedel K, Allaway GP. Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19:107–13. https://doi.org/10.1177/095632020801900301 . (PMID: 10.1177/09563202080190030119024627)
Frew Q, Rennekampff HO, Dziewulski P, Moiemen N. BBW-11 Study Group; Zahn T, Hartmann B. Betulin wound gel accelerated healing of superficial partial thickness burns: results of a randomized, intra-individually controlled, phase III trial with 12-months follow-up. Burns. 2019;45:876–90. https://doi.org/10.1016/j.burns.2018.10.019 . (PMID: 10.1016/j.burns.2018.10.01930559054)
Xiao S, Tian Z, Wang Y, Si L, Zhang L, Zhou D. Recent progress in the antiviral activity and mechanism study of pentacyclic triterpenoids and their derivatives. Med Res Rev. 2018;38:951–76. https://doi.org/10.1002/med.21484 . (PMID: 10.1002/med.21484293504077168445)
Lee KH. Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach. J Nat Prod. 2010;73:500–16. https://doi.org/10.1021/np900821e . (PMID: 10.1021/np900821e201876352893734)
Kashiwada Y, Nagao T, Hashimoto A, Ikeshiro Y, Okabe H, Cosentino LM, Lee KH. Anti-AIDS agents 38. Anti-HIV activity of 3-O-acyl ursolic acid derivatives. J Nat Prod. 2000;63:1619–22. https://doi.org/10.1021/np990633v . (PMID: 10.1021/np990633v11141100)
Deng SL, Baglin I, Nour M, Flekhter O, Vita C, Cavé C. Synthesis of ursolic phosphonate derivatives as potential anti-HIV agents. Phosphorus Sulfur Silicon Relat Elem 2007;182:951–67. https://doi.org/10.1080/10426500601088838 . (PMID: 10.1080/10426500601088838)
Gong Y, Raj KM, Luscombe CA, Gadawski I, Tam T, Chu J, Gibson D, Carlson R, Sacks SL. The synergistic effects of betulin with acyclovir against herpes simplex viruses. Antivir Res. 2004;64:127–30. https://doi.org/10.1016/j.antiviral.2004.05.006 . (PMID: 10.1016/j.antiviral.2004.05.00615498608)
Baltina LA, Flekhter OB, Nigmatullina LR, Boreko EI, Pavlova NI, Nikolaeva SN, Savinova OV, Tolstikov GA. Lupane triterpenes and derivatives with antiviral activity. Bioorg Med Chem Lett. 2003;13:3549–52. https://doi.org/10.1016/s0960-894x(03)00714-5 . (PMID: 10.1016/s0960-894x(03)00714-514505668)
Pavlova NI, Savinova OV, Nikolaeva SN, Boreko EI, Flekhter OB. Antiviral activity of betulin, betulinic and betulonic acids against some enveloped and non-enveloped viruses. Fitoterapia. 2003;74:489–92. https://doi.org/10.1016/s0367-326x(03)00123-0 . (PMID: 10.1016/s0367-326x(03)00123-012837369)
Kazakova OB, Giniyatullina GV, Yamansarov EY, Tolstikov GA. Betulin and ursolic acid synthetic derivatives as inhibitors of Papilloma virus. Bioorg Med Chem Lett. 2010;20:4088–90. https://doi.org/10.1016/j.bmcl.2010.05.083 . (PMID: 10.1016/j.bmcl.2010.05.08320558062)
Kazakova OB, Medvedeva NI, Baikova IP, Tolstikov GA, Lopatina TV, Yunusov MS, Zaprutko L. Synthesis of triterpenoid acylates: effective reproduction inhibitors of influenza A (H1N1) and papilloma viruses. Russ J Bioorg Chem. 2010;36:771–8. https://doi.org/10.1134/S1068162010060142 . (PMID: 10.1134/S1068162010060142322147807089435)
Khusnutdinova EF, Kazakova OB, Lobov AN, Kukovinets OS, Suponitsky KY, Meyers CB, Prichard MN. Synthesis of A-ring quinolones, nine-membered oxolactams and spiroindoles by oxidative transformations of 2,3-indolotriterpenoids. Org Biomol Chem. 2019;17:585–97. https://doi.org/10.1039/c8ob02624f . (PMID: 10.1039/c8ob02624f30574983)
Savinova OV, Pavlova NI, Boreko EI. [New betulin derivatives in combination with rimantadine for inhibition of influenza virus reproduction]. Antibiot Khimioter. 2009;54:16–20. (PMID: 20052912)
Karagöz AÇ, Leidenberger M, Hahn F, Hampel F, Friedrich O, Marschall M, Kappes B, Tsogoeva SB. Synthesis of new betulinic acid/betulin-derived dimers and hybrids with potent antimalarial and antiviral activities. Bioorg Med Chem. 2019;27:110–5. https://doi.org/10.1016/j.bmc.2018.11.018 . (PMID: 10.1016/j.bmc.2018.11.01830503412)
Dinh Ngoc T, Moons N, Kim Y, De Borggraeve W, Mashentseva A, Andrei G, Snoeck R, Balzarini J, Dehaen W. Synthesis of triterpenoid triazine derivatives from allobetulone and betulonic acid with biological activities. Bioorg Med Chem. 2014;22:3292–3300. https://doi.org/10.1016/j.bmc.2014.04.061 . (PMID: 10.1016/j.bmc.2014.04.06124844757)
Pohjala L, Alakurtti S, Ahola T, Yli-Kauhaluoma J, Tammela P. Betulin-derived compounds as inhibitors of alphavirus replication. J Nat Prod. 2009;72:1917–26. https://doi.org/10.1021/np9003245 . (PMID: 10.1021/np900324519839605)
Spivak AY, Galimshina ZR, Nedopekina DA, Odinokov VN. Synthesis of new C-2 triazole-linked analogs of triterpenoid pentacyclic saponins. Chem Nat Compd. 2018;54:315–23. https://doi.org/10.1007/s10600-018-2331-1 . (PMID: 10.1007/s10600-018-2331-1)
Spivak AY, Gubaidullin RR, Galimshina ZR, Nedopekina DA, Odinokov VN. Effective synthesis of novel C(2)-propargyl derivatives of betulinic and ursolic acids and their conjugation with β-D-glucopyranoside azides via click chemistry. Tetrahedron. 2016;72:1249–56. https://doi.org/10.1016/J.TET.2016.01.024 . (PMID: 10.1016/J.TET.2016.01.024)
Spivak AY, Nedopekina DA, Galimshina ZR, Khalitova RR, Sadretdinova ZR, Gubaidullin RR, Odinokov VN. Click chemistry-assisted synthesis of novel C-2 triazole-linked betulinic acid conjugates with azidothymidine as potential anti-HIV agents. Arkivoc. 2018;VII:1–19. https://doi.org/10.24820/ark.5550190.p010.632 . (PMID: 10.24820/ark.5550190.p010.632)
Khusnutdinova EF, Bremond P, Petrova AV, Kukovinets OS, Kazakova OB. Synthesis of lupane mono- and bis-C19-(1,2,3-triazolyl)-triterpenoids by “Click” reaction. Lett Org Chem. 2017;14:743–7. (PMID: 10.2174/1570178614666170918120624)
Pokorny J, Borkova L, Urban M. Click reactions in chemistry of triterpenes—advances towards development of potential therapeutics. Curr Med Chem. 2018;25:636–58. https://doi.org/10.2174/0929867324666171009122612 . (PMID: 10.2174/092986732466617100912261228990518)
Csuk R, Deigner HP. The potential of click reactions for the synthesis of bioactive triterpenes. Bioorg Med Chem Lett. 2019;29:949–58. https://doi.org/10.1016/j.bmcl.2019.02.020 . (PMID: 10.1016/j.bmcl.2019.02.02030799214)
Yu F, Wang Q, Zhang Z, Peng Y, Qiu Y, Shi Y, Zheng Y, Xiao S, Wang H, Huang X, Zhu L, Chen K, Zhao C, Zhang C, Yu M, Sun D, Zhang L, Zhou D. Development of oleanane-type triterpenes as a new class of HCV entry inhibitors. J Med Chem. 2013;56:4300–4019. https://doi.org/10.1021/jm301910a . (PMID: 10.1021/jm301910a23662817)
Xiao S, Wang Q, Si L, Shi Y, Wang H, Yu F, Zhang Y, Li Y, Zheng Y, Zhang C, Wang C, Zhang L, Zhou D. Synthesis and anti-HCV entry activity studies of β-cyclodextrin-pentacyclic triterpene conjugates. ChemMedChem. 2014;9:1060–70. https://doi.org/10.1002/cmdc.201300545 . (PMID: 10.1002/cmdc.20130054524623716)
Xiao S, Wang Q, Si L, Zhou X, Zhang Y, Zhang L, Zhou D. Synthesis and biological evaluation of novel pentacyclic triterpene α-cyclodextrin conjugates as HCV entry inhibitors. Eur J Med Chem. 2016;124:1–9. https://doi.org/10.1016/j.ejmech.2016.08.020 . (PMID: 10.1016/j.ejmech.2016.08.02027565552)
Wang C, Lu L, Na H, Li X, Wang Q, Jiang X, Xu X, Yu F, Zhang T, Li J, Zhang Z, Zheng B, Liang G, Cai L, Jiang S, Liu K. Conjugation of a nonspecific antiviral sapogenin with a specific HIV fusion inhibitor: a promising strategy for discovering new antiviral therapeutics. J Med Chem. 2014;57:7342–54. https://doi.org/10.1021/jm500763m . (PMID: 10.1021/jm500763m25156906)
Roman G. Mannich bases in medicinal chemistry and drug design. Eur J Med Chem. 2015;89:743–816. https://doi.org/10.1016/j.ejmech.2014.10.076 . (PMID: 10.1016/j.ejmech.2014.10.07625462280)
Kazakova OB, Medvedeva NI, Tolstikov GA, Kukovinets OS, Yamansarov EY, Spirikhin LV, Gubaidullin AT. Synthesis of terminal acetylenes using POCl 3 in pyridine as applied to natural triterpenoids. Mendeleev Commun. 2010;20:234–6. https://doi.org/10.1016/j.mencom.2010.06.018 . (PMID: 10.1016/j.mencom.2010.06.018)
Khusnutdinova EF, Apryshko GN, Petrova AV, Kukovinets OS, Kazakova OB. The synthesis and selective cytotoxicity of new Mannich bases, derivatives of 19- and 28-alkynyltriterpenoids. Russ J Bioorg Chem. 2018;44:123–7. https://doi.org/10.1134/S1068162018010090 . (PMID: 10.1134/S1068162018010090)
Khusnutdinova EF, Petrova AV, Kukovinets OS, Kazakova OB. Synthesis and cytotoxicity of 28-N-propargylaminoalkylated 2,3-indolotriterpenic acids. Nat Prod Commun. 2018;13:665–8. https://doi.org/10.1177/1934578X1801300603 . (PMID: 10.1177/1934578X1801300603)
Kazakova O, Tret’yakova E, Baev D. Evaluation of A-azepano-triterpenoids and related derivatives as antimicrobial and antiviral agents. J Antibiot. 2021;74:559–73. https://doi.org/10.1038/s41429-021-00448-9 . (PMID: 10.1038/s41429-021-00448-9)
Babaev M, Khusnutdinova E, Lobov A, Galimova Z, Petrova A, Rybalova T, Nguyen HTT, Meyers C, Prichard M, Kazakova O. Allobetulone rearrangement to l8αH,19βH-ursane triterpenoids with antiviral activity. Nat Prod Res. 2022;36:3286–96. https://doi.org/10.1080/14786419.2020.1855159 . (PMID: 10.1080/14786419.2020.185515933287588)
Smee DF, Huffman JH, Morrison AC, Barnard DL, Sidwell RW. Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities. Antimicrob Agents Chemother. 2001;45:743–8. https://doi.org/10.1128/AAC.45.3.743-748.2001 . (PMID: 10.1128/AAC.45.3.743-748.20011118135490367)
Prichard MN, Williams JD, Komazin-Meredith G, Khan AR, Price NB, Jefferson GM, Harden EA, Hartline CB, Peet NP, Bowlin TL. Synthesis and antiviral activities of methylenecyclopropane analogs with 6-alkoxy and 6-alkylthio substitutions that exhibit broad-spectrum antiviral activity against human herpesviruses. Antimicrob Agents Chemother. 2013;57:3518–27. https://doi.org/10.1128/AAC.00429-13 . (PMID: 10.1128/AAC.00429-13236693813719742)
المشرفين على المادة: 0 (oleanane)
6SMK8R7TGJ (Oleanolic Acid)
0 (Triterpenes)
0 (Antiviral Agents)
0 (Lupanes)
تواريخ الأحداث: Date Created: 20231107 Date Completed: 20240108 Latest Revision: 20240416
رمز التحديث: 20240416
DOI: 10.1038/s41429-023-00672-5
PMID: 37935823
قاعدة البيانات: MEDLINE
الوصف
تدمد:1881-1469
DOI:10.1038/s41429-023-00672-5