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Biosynthesis and half-life of MBX-2168-triphosphate in herpes virus-infected cells.
Sauer HE, Nguyen ML, Williams JD, Bowlin TL, Gentry BG. Sauer HE, et al. Antiviral Res. 2020 Mar;175:104713. doi: 10.1016/j.antiviral.2020.104713. Epub 2020 Jan 20. Antiviral Res. 2020. PMID: 31968222 Free PMC article.
To that end, herpes virus-infected cells were incubated with MBX-2168, synguanol, GCV, or ACV. Incubation of HCMV-infected cells with five times the EC(50) of MBX-2168 (4.0 muM), synguanol (10.5 muM), or GCV (25 muM) resulted in a time-dependent increase in triphosp …
To that end, herpes virus-infected cells were incubated with MBX-2168, synguanol, GCV, or ACV. Incubation of HCMV-infected cells with …
Cytomegalovirus mutants resistant to ganciclovir and cidofovir differ in susceptibilities to synguanol and its 6-ether and 6-thioether derivatives.
Chou S, Komazin-Meredith G, Williams JD, Bowlin TL. Chou S, et al. Antimicrob Agents Chemother. 2014;58(3):1809-12. doi: 10.1128/AAC.02544-13. Epub 2013 Dec 30. Antimicrob Agents Chemother. 2014. PMID: 24379208 Free PMC article.
The methylenecyclopropane nucleoside (MCPN) analogs synguanol and its 6-alkoxy (MBX2168) and 6-alkylthio (MBX1616) derivatives retained good in vitro activities against several common ganciclovir-resistant UL97 kinase variants of human cytomegalovirus. ...
The methylenecyclopropane nucleoside (MCPN) analogs synguanol and its 6-alkoxy (MBX2168) and 6-alkylthio (MBX1616) derivatives retain …
Stereoselective approach to the Z-isomers of methylenecyclopropane analogues of nucleosides: a new synthesis of antiviral synguanol.
Wu Z, Zhou S, Zemlicka J. Wu Z, et al. Nucleosides Nucleotides Nucleic Acids. 2009 Mar;28(3):165-74. doi: 10.1080/15257770902831060. Nucleosides Nucleotides Nucleic Acids. 2009. PMID: 19333855 Free PMC article.
Stereoselective synthesis of antiviral synguanol (1) is described. Reaction of 6-benzyloxy-2-(dimethylaminomethyleneamino)purine (10) with ethyl (cis,trans)-2-chloro-2-(chloromethyl) cyclopropane-1-carboxylate (2c) under the conditions of alkylation-elimination gave (Z)-6- …
Stereoselective synthesis of antiviral synguanol (1) is described. Reaction of 6-benzyloxy-2-(dimethylaminomethyleneamino)purine (10) …
Z-isomers of 2-hydroxymethylcyclopropylidenemethyl adenine (synadenol) and guanine (synguanol) are active against ganciclovir- and foscarnet-resistant human cytomegalovirus UL97 mutants.
Baldanti F, Sarasini A, Drach JC, Zemlicka J, Gerna G. Baldanti F, et al. Antiviral Res. 2002 Dec;56(3):273-8. doi: 10.1016/s0166-3542(02)00129-8. Antiviral Res. 2002. PMID: 12406510
Analysis of synadenol and synguanol susceptibility of a series of HCMV isolates from immunocompromised untreated patients and from patients with treatment failure due to the emergence of GCV- and foscarnet (PFA)-resistant HCMV strains demonstrated that synadenol and syn …
Analysis of synadenol and synguanol susceptibility of a series of HCMV isolates from immunocompromised untreated patients and from pa …
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.
De Clercq E, Andrei G, Snoeck R, De Bolle L, Naesens L, Degrève B, Balzarini J, Zhang Y, Schols D, Leyssen P, Ying C, Neyts J. De Clercq E, et al. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):271-85. doi: 10.1081/NCN-100002298. Nucleosides Nucleotides Nucleic Acids. 2001. PMID: 11563039 Review.
In recent years, several new guanosine analogues have been developed, including the 3-membered cyclopropylmethyl and -methenyl derivatives (A-5021 and synguanol) and the 6-membered D- and L-cyclohexenyl derivatives. The activity of the acyclic/carbocyclic guanosine analogu …
In recent years, several new guanosine analogues have been developed, including the 3-membered cyclopropylmethyl and -methenyl derivatives ( …
Activation of 6-Alkoxy-Substituted Methylenecyclopropane Nucleoside Analogs Requires Enzymatic Modification by Adenosine Deaminase-Like Protein 1.
Vollmer KJ, Burns AC, Sauer HE, Williams JD, Komazin-Meredith G, Cardinale S, Butler M, Aron Z, Hussein I, Busch MG, Bowlin TL, Gentry BG. Vollmer KJ, et al. Antimicrob Agents Chemother. 2019 Sep 23;63(10):e01301-19. doi: 10.1128/AAC.01301-19. Print 2019 Oct. Antimicrob Agents Chemother. 2019. PMID: 31332074 Free PMC article.
Purified ADAL-1 demonstrated time-dependent removal of the moiety on the guanine ring of MBX-2168-monophosphate (MP), with a K(m) of 17.5 2.4 muM and a V(max) of 0.12 0.04 nmol min(-1) Finally, synguanol-TP demonstrated concentration-dependent inhibition of HSV-1 UL30 and …
Purified ADAL-1 demonstrated time-dependent removal of the moiety on the guanine ring of MBX-2168-monophosphate (MP), with a K(m) of 17.5 2. …
In vitro activities of methylenecyclopropane analogues of nucleosides and their phosphoralaninate prodrugs against cytomegalovirus and other herpesvirus infections.
Rybak RJ, Hartline CB, Qiu YL, Zemlicka J, Harden E, Marshall G, Sommadossi JP, Kern ER. Rybak RJ, et al. Antimicrob Agents Chemother. 2000 Jun;44(6):1506-11. doi: 10.1128/AAC.44.6.1506-1511.2000. Antimicrob Agents Chemother. 2000. PMID: 10817700 Free PMC article.
The compounds were also tested for efficacy against herpes simplex virus types 1 and 2, varicella-zoster virus, and Epstein-Barr virus, and some had levels of activity that were comparable to that of acyclovir. In addition, the compounds synguanol (QYL-438) and 2-amino-6-c …
The compounds were also tested for efficacy against herpes simplex virus types 1 and 2, varicella-zoster virus, and Epstein-Barr virus, and …
Effective treatment of murine cytomegalovirus infections with methylenecyclopropane analogues of nucleosides.
Rybak RJ, Zemlicka J, Qiu YL, Hartline CB, Kern ER. Rybak RJ, et al. Antiviral Res. 1999 Oct;43(3):175-88. doi: 10.1016/s0166-3542(99)00043-1. Antiviral Res. 1999. PMID: 10551375
Intraperitoneal (i.p.) inoculation of 3-week-old Balb/c mice with 2.0 x 10(5) plaque forming units (pfu) of MCMV results in an acute, lethal infection with rapid virus replication in visceral and glandular tissue, thus, making it an ideal model for identifying compounds that have …
Intraperitoneal (i.p.) inoculation of 3-week-old Balb/c mice with 2.0 x 10(5) plaque forming units (pfu) of MCMV results in an acute, lethal …
Synthesis and antiviral activities of methylenecyclopropane analogs with 6-alkoxy and 6-alkylthio substitutions that exhibit broad-spectrum antiviral activity against human herpesviruses.
Prichard MN, Williams JD, Komazin-Meredith G, Khan AR, Price NB, Jefferson GM, Harden EA, Hartline CB, Peet NP, Bowlin TL. Prichard MN, et al. Antimicrob Agents Chemother. 2013 Aug;57(8):3518-27. doi: 10.1128/AAC.00429-13. Epub 2013 May 13. Antimicrob Agents Chemother. 2013. PMID: 23669381 Free PMC article.
CPV has two hydroxymethyl groups on the methylenecyclopropane ring, but analogs with a single hydroxymethyl group, such as the prototypical (S)-synguanol, are also active and exhibit a broader spectrum of antiviral activity that also includes hepatitis B virus and human im …
CPV has two hydroxymethyl groups on the methylenecyclopropane ring, but analogs with a single hydroxymethyl group, such as the prototypical …