Synthesis and Evaluation of Novel 5‐O‐(4‐C‐Aminoalkyl‐β‐D‐ribofuranosyl) Apramycin Derivatives for the Inhibition of Gram‐Negative Pathogens Carrying the Aminoglycoside Phosphotransferase(3′)‐Ia Resistance Determinant
We report the synthesis and evaluation of two new apramycin 5‐O‐β‐d‐ribofuranosides, or apralogs, carrying aminoalkyl branches at the ribofuranose 4‐position. This novel modification conveys excellent activity for the inhibition of protein synthesis by wild‐type bacterial ribosomes and corresponding...
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| Published in: | Helvetica chimica acta Vol. 106; no. 11 |
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| Main Authors: | , , , , , , , |
| Format: | Journal Article |
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| Abstract | We report the synthesis and evaluation of two new apramycin 5‐O‐β‐d‐ribofuranosides, or apralogs, carrying aminoalkyl branches at the ribofuranose 4‐position. This novel modification conveys excellent activity for the inhibition of protein synthesis by wild‐type bacterial ribosomes and correspondingly high antibacterial activity against several Gram‐negative pathogens. Notably, these new modifications overcome the reduction of antibacterial activity in other 2‐deoxystreptamine‐type aminoglycosides carrying a 5‐O‐ribofuranosyl moiety when challenged by the presence of an aminoglycoside phosphotransferase enzyme capable of acting on the ribose 5‐position. |
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| AbstractList | We report the synthesis and evaluation of two new apramycin 5‐
O
‐β‐
d
‐ribofuranosides, or apralogs, carrying aminoalkyl branches at the ribofuranose 4‐position. This novel modification conveys excellent activity for the inhibition of protein synthesis by wild‐type bacterial ribosomes and correspondingly high antibacterial activity against several Gram‐negative pathogens. Notably, these new modifications overcome the reduction of antibacterial activity in other 2‐deoxystreptamine‐type aminoglycosides carrying a 5‐
O
‐ribofuranosyl moiety when challenged by the presence of an aminoglycoside phosphotransferase enzyme capable of acting on the ribose 5‐position. We report the synthesis and evaluation of two new apramycin 5‐O‐β‐d‐ribofuranosides, or apralogs, carrying aminoalkyl branches at the ribofuranose 4‐position. This novel modification conveys excellent activity for the inhibition of protein synthesis by wild‐type bacterial ribosomes and correspondingly high antibacterial activity against several Gram‐negative pathogens. Notably, these new modifications overcome the reduction of antibacterial activity in other 2‐deoxystreptamine‐type aminoglycosides carrying a 5‐O‐ribofuranosyl moiety when challenged by the presence of an aminoglycoside phosphotransferase enzyme capable of acting on the ribose 5‐position. We report the synthesis and evaluation of two new apramycin 5‐O‐β‐d‐ribofuranosides, or apralogs, carrying aminoalkyl branches at the ribofuranose 4‐position. This novel modification conveys excellent activity for the inhibition of protein synthesis by wild‐type bacterial ribosomes and correspondingly high antibacterial activity against several Gram‐negative pathogens. Notably, these new modifications overcome the reduction of antibacterial activity in other 2‐deoxystreptamine‐type aminoglycosides carrying a 5‐O‐ribofuranosyl moiety when challenged by the presence of an aminoglycoside phosphotransferase enzyme capable of acting on the ribose 5‐position.Dedicated to our valued friend and respected collaborator Andrea Vasella, on the occasion of his 80th birthday |
| Author | Hobbie, Sven N. Kiliç, Fatmanur Suna, Edgars Böttger, Erik C. Hartmann, Maximilian Haldimann, Klara Lubriks, Dmitrijs Crich, David |
| Author_xml | – sequence: 1 givenname: Dmitrijs orcidid: 0000-0002-8014-4172 surname: Lubriks fullname: Lubriks, Dmitrijs organization: Latvian Institute of Organic Synthesis – sequence: 2 givenname: Klara surname: Haldimann fullname: Haldimann, Klara organization: University of Zurich – sequence: 3 givenname: Fatmanur surname: Kiliç fullname: Kiliç, Fatmanur organization: University of Zurich – sequence: 4 givenname: Maximilian surname: Hartmann fullname: Hartmann, Maximilian organization: University of Zurich – sequence: 5 givenname: Erik C. orcidid: 0000-0002-2570-0121 surname: Böttger fullname: Böttger, Erik C. organization: University of Zurich – sequence: 6 givenname: Sven N. orcidid: 0000-0002-9205-0384 surname: Hobbie fullname: Hobbie, Sven N. organization: University of Zurich – sequence: 7 givenname: Edgars orcidid: 0000-0002-3078-0576 surname: Suna fullname: Suna, Edgars email: edgars@osi.lv organization: Latvian Institute of Organic Synthesis – sequence: 8 givenname: David orcidid: 0000-0003-2400-0083 surname: Crich fullname: Crich, David email: David.crich@uga.edu organization: University of Georgia |
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| Cites_doi | 10.1073/pnas.1204073109 10.1039/C5MD00344J 10.1038/35030019 10.1146/annurev-biochem-062917-011942 10.1128/AAC.00965-08 10.1016/j.idc.2016.02.011 10.1093/jac/dky546 10.1128/aac.01510-21 10.1021/jacs.9b12420 10.1002/bip.10414 10.1016/j.bmcl.2014.04.050 10.1021/ol5036535 10.1021/acsinfecdis.2c00557 10.1055/s-2001-17485 10.1039/D2MD00459C 10.3390/ijms21176133 10.7164/antibiotics.34.1434 10.3390/antibiotics12010025 10.1021/acs.oprd.2c00013 10.1021/acs.joc.5b00607 10.1093/jac/dkac225 10.1002/cmdc.202200120 10.1021/acsinfecdis.9b00441 10.1007/978-1-4614-1400-1_7 10.1093/nar/gkm658 10.1002/anie.201310843 10.1016/j.trsl.2020.02.008 10.1002/cmdc.202000726 10.1021/jacs.1c00076 10.1002/cmdc.202200486 10.1038/ja.2017.117 10.1021/acsinfecdis.1c00158 10.2741/Wright 10.1038/ng0793-289 10.1039/C5MD00384A 10.1016/j.cmi.2020.12.004 10.1073/pnas.0811258106 10.1016/j.ebiom.2021.103652 10.1021/jacs.9b11601 |
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| References | 2021; 27 2021; 7 2015; 17 2023; 14 2023; 12 2019; 74 2023; 18 2020; 220 2020; 142 2023; 9 2016; 30 2022; 26 2014; 24 1999; 4 2008; 105 2015; 80 2022; 66 2021; 143 2018; 87 2021; 73 2007; 35 1993; 4 2012; 109 2000; 407 2020; 6 2021; 16 2016; 7 2009; 53 2003; 70 2001 2018; 71 2022; 77 2020; 21 2022; 17 1981; 34 2014; 53 e_1_2_10_23_1 e_1_2_10_24_1 e_1_2_10_21_1 e_1_2_10_22_1 e_1_2_10_20_1 e_1_2_10_41_1 e_1_2_10_40_1 e_1_2_10_1_1 e_1_2_10_2_1 e_1_2_10_4_1 e_1_2_10_18_1 e_1_2_10_3_1 e_1_2_10_19_1 e_1_2_10_6_1 e_1_2_10_16_1 e_1_2_10_39_1 e_1_2_10_5_1 e_1_2_10_17_1 e_1_2_10_38_1 e_1_2_10_8_1 e_1_2_10_14_1 e_1_2_10_37_1 e_1_2_10_7_1 e_1_2_10_15_1 e_1_2_10_36_1 e_1_2_10_12_1 e_1_2_10_35_1 e_1_2_10_9_1 e_1_2_10_13_1 e_1_2_10_34_1 e_1_2_10_10_1 e_1_2_10_33_1 e_1_2_10_11_1 e_1_2_10_32_1 e_1_2_10_31_1 e_1_2_10_30_1 e_1_2_10_29_1 e_1_2_10_27_1 e_1_2_10_28_1 e_1_2_10_25_1 e_1_2_10_26_1 |
| References_xml | – start-page: 1590 year: 2001 end-page: 1592 article-title: ‘Hydrogenolysis-free Hydrogenation by Pd Black Powder Catalyst’ publication-title: Synlett – volume: 21 start-page: 6133 year: 2020 article-title: ‘Epidemiologic, Phenotypic, and Structural Characterization of Aminoglycoside-Resistance Gene ’ publication-title: Int. J. Mol. Sci. – volume: 34 start-page: 1434 year: 1981 end-page: 1446 article-title: ‘Aminoglycoside Antibiotics. XIV. Synthesis and Activity of 6- -(3-Amino-3-deoxy-α- -glucopyranosyl)- and 5- -(β- -ribofuranosyl)apramycins’ publication-title: J. Antibiot. – volume: 143 start-page: 5038 year: 2021 end-page: 5043 article-title: ‘Mechanistic Investigation of 1,2-Diol Dehydration of Paromamine Catalyzed by the Radical -Adenosyl- -methionine Enzyme AprD4’ publication-title: J. Am. Chem. Soc. – volume: 14 start-page: 624 year: 2023 end-page: 643 article-title: ‘Ribosome-targeting antibiotics and resistance ribosomal RNA methylation’ publication-title: RSC Med. Chem. – volume: 24 start-page: 2699 year: 2014 end-page: 2702 article-title: ‘Synthesis of 2′- ,4′- -alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase’ publication-title: Bioorg. Med. Chem. Lett. – volume: 12 start-page: 25 year: 2023 article-title: ‘Synthesis, Antibacterial and Antiribosomal Activity of the 3 -Aminoalkyl Modification in the Ribofuranosyl Ring of Apralogs (5- -Ribofuranosyl Apramycins)’ publication-title: Antibiotics – volume: 4 start-page: 289 year: 1993 end-page: 294 article-title: ‘Mitochondrial ribosomal RNA mutation associated with both antibiotic-induced and non-syndromic deafness’ publication-title: Nat. Genetics – volume: 142 start-page: 530 year: 2020 end-page: 544 article-title: ‘Apralogs: Apramycin 5- -Glycosides and Ethers with Improved Antibacterial Activity and Ribosomal Selectivity and Reduced Susceptibility to the Aminoacyltranserferase (3)-IV Resistance Determinant’ publication-title: J. Am. Chem. Soc. – volume: 109 start-page: 10984 year: 2012 end-page: 10989 article-title: ‘Dissociation of antibacterial activity and aminoglycoside ototoxicity in the 4-monosubstituted 2-deoxystreptamine apramycin’ publication-title: Proc. Natl. Acad. Sci. USA – volume: 35 start-page: 6086 year: 2007 end-page: 6093 article-title: ‘Engineering the rRNA decoding site of eukaryotic cytosolic ribosomes in bacteria’ publication-title: Nucl. Acids Res. – volume: 7 start-page: 103 year: 2016 end-page: 113 article-title: ‘Drug-target networks in aminoglycoside resistance: hierarchy of priority in structural drug design’ publication-title: MedChemComm – volume: 105 start-page: 20888 year: 2008 end-page: 20893 article-title: ‘Genetic analysis of interactions with eukaryotic rRNA identify the mitoribosome as target in aminoglycoside ototoxicity’ publication-title: Proc. Natl. Acad. Sci. USA – volume: 17 start-page: 828 year: 2015 end-page: 831 article-title: ‘Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3-Keto Furanose’ publication-title: Org. Lett. – volume: 7 start-page: 2413 year: 2021 end-page: 2424 article-title: ‘Synthesis and Antibacterial Activity of Propylamycin Derivatives Functionalized at the 5′′- and Other Positions with a View to Overcoming Resistance due to Aminoglycoside Modifying Enzymes’ publication-title: ACS Infect. Dis. – volume: 17 year: 2022 article-title: ‘Structure-Activity Relationships for 5′′-Modifications of 4,5-Aminoglycoside Antibiotics’ publication-title: ChemMedChem. – volume: 26 start-page: 1289 year: 2022 end-page: 1307 article-title: ‘Efficient Divergent Synthesis of 2′- ,4′- -Ethylene-Bridged Nucleic Acid (ENA) Phosphoramidites’ publication-title: Org. Process Res. Dev. – volume: 53 start-page: 8840 year: 2014 end-page: 8869 article-title: ‘The Evolving Role of Chemical Synthesis in Antibacterial Drug Discovery’ publication-title: Angew. Chem. Int. Ed. – volume: 142 start-page: 3077 year: 2020 end-page: 3087 article-title: ‘Chemical Modifications Reduce Auditory Cell Damage Induced by Aminoglycoside Antibiotics’ publication-title: J. Am. Chem. Soc. – volume: 70 start-page: 42 year: 2003 end-page: 57 article-title: ‘Molecular recognition of aminoglycoside antibiotics by ribosomal RNA and resistance enzymes: An analysis of x-ray crystal structures’ publication-title: Biopolymers – volume: 77 start-page: 2718 year: 2022 end-page: 2728 article-title: ‘Population pharmacokinetics of apramycin from first-in-human plasma and urine data to support prediction of efficacious dose’ publication-title: J. Antimicrob. Chemother. – volume: 16 start-page: 335 year: 2021 end-page: 339 article-title: ‘An Advanced Apralog with Increased in vitro and in vivo Activity toward Gram-negative Pathogens and Reduced ex vivo Cochleotoxicity’ publication-title: ChemMedChem – volume: 74 start-page: 944 year: 2019 end-page: 952 article-title: ‘ activity of apramycin against multidrug-, carbapenem-, and aminoglycoside-resistant Enterobacteriaceae and ’ publication-title: J. Antimicrob. Chemother. – volume: 4 start-page: 9 year: 1999 end-page: 21 article-title: ‘Aminoglycoside phosphotransferases: proteins, structure, and mechanism’ publication-title: Front. Biosci. (Landmark Ed) – volume: 73 year: 2021 article-title: ‘Antibacterial activity of apramycin at acidic pH warrants wide therapeutic window in the treatment of complicated urinary tract infections and acute pyelonephritis’ publication-title: eBioMedicine – volume: 6 start-page: 168 year: 2020 end-page: 172 article-title: ‘Aminoglycosides: Time for Resurrection of a Neglected Class of Antibacterials?’ publication-title: ACS Infect. Dis. – volume: 87 start-page: 451 year: 2018 end-page: 478 article-title: ‘Ribosome-Targeting Antibiotics: Modes of Action, Mechanisms of Resistance, and Implications for Drug Design’ publication-title: Annu. Rev. Biochem. – volume: 66 start-page: e01510 year: 2022 end-page: 21 article-title: ‘Apramycin Overcomes the Inherent Lack of Antimicrobial Bactericidal Activity in ’ publication-title: Antimicrob. Agents Chemother. – volume: 53 start-page: 4612 year: 2009 end-page: 4618 article-title: ‘Interaction of Aminoglycosides with Human Mitochondrial 12S rRNA Carrying the Deafness-Associated Mutation’ publication-title: Antimicrob. Agents Chemother. – volume: 220 start-page: 14 year: 2020 end-page: 32 article-title: ‘New strategies and structural considerations in development of therapeutics for carbapenem-resistant ’ publication-title: Translat. Res. – volume: 27 start-page: 1315 year: 2021 end-page: 1321 article-title: ‘Efficacy of EBL-1003 (apramycin) against lung infections in mice’ publication-title: Clin. Microbiol. Infect. – volume: 18 year: 2023 article-title: ‘Importance of Co-operative Hydrogen Bonding in the Apramycin-Ribosomal Decoding A-Site Interaction’ publication-title: ChemMedChem – volume: 71 start-page: 4 year: 2018 end-page: 14 article-title: ‘Destination of aminoglycoside antibiotics in the ‘post-antibiotic era’’ publication-title: J. Antibiot. – volume: 30 start-page: 523 year: 2016 end-page: 537 article-title: ‘Aminoglycoside Resistance: The Emergence of Acquired 16S Ribosomal RNA Methyltransferases’ publication-title: Infect. Dis. Clin. North Am. – volume: 80 start-page: 5337 year: 2015 end-page: 5343 article-title: ‘Modular Synthesis of Constrained Ethyl (cEt) Purine and Pyrimidine Nucleosides’ publication-title: J. Org. Chem. – volume: 407 start-page: 340 year: 2000 end-page: 348 article-title: ‘Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics’ publication-title: Nature – volume: 9 start-page: 886 year: 2023 end-page: 898 article-title: ‘Aprosamine Derivatives Active against Multidrug-Resistant Gram-Negative Bacteria’ publication-title: ACS Infect. Dis. – volume: 7 start-page: 11 year: 2016 end-page: 27 article-title: ‘Mechanisms of resistance to aminoglycoside antibiotics: overview and perspectives’ publication-title: MedChemComm – ident: e_1_2_10_9_1 doi: 10.1073/pnas.1204073109 – ident: e_1_2_10_5_1 doi: 10.1039/C5MD00344J – ident: e_1_2_10_30_1 doi: 10.1038/35030019 – ident: e_1_2_10_31_1 doi: 10.1146/annurev-biochem-062917-011942 – ident: e_1_2_10_35_1 doi: 10.1128/AAC.00965-08 – ident: e_1_2_10_7_1 doi: 10.1016/j.idc.2016.02.011 – ident: e_1_2_10_11_1 doi: 10.1093/jac/dky546 – ident: e_1_2_10_13_1 doi: 10.1128/aac.01510-21 – ident: e_1_2_10_20_1 doi: 10.1021/jacs.9b12420 – ident: e_1_2_10_36_1 doi: 10.1002/bip.10414 – ident: e_1_2_10_39_1 doi: 10.1016/j.bmcl.2014.04.050 – ident: e_1_2_10_27_1 doi: 10.1021/ol5036535 – ident: e_1_2_10_23_1 doi: 10.1021/acsinfecdis.2c00557 – ident: e_1_2_10_29_1 doi: 10.1055/s-2001-17485 – ident: e_1_2_10_38_1 – ident: e_1_2_10_8_1 doi: 10.1039/D2MD00459C – ident: e_1_2_10_16_1 doi: 10.3390/ijms21176133 – ident: e_1_2_10_19_1 doi: 10.7164/antibiotics.34.1434 – ident: e_1_2_10_21_1 doi: 10.3390/antibiotics12010025 – ident: e_1_2_10_40_1 – ident: e_1_2_10_37_1 doi: 10.1021/acs.oprd.2c00013 – ident: e_1_2_10_28_1 doi: 10.1021/acs.joc.5b00607 – ident: e_1_2_10_15_1 doi: 10.1093/jac/dkac225 – ident: e_1_2_10_24_1 doi: 10.1002/cmdc.202200120 – ident: e_1_2_10_1_1 doi: 10.1021/acsinfecdis.9b00441 – ident: e_1_2_10_2_1 doi: 10.1007/978-1-4614-1400-1_7 – ident: e_1_2_10_32_1 doi: 10.1093/nar/gkm658 – ident: e_1_2_10_14_1 doi: 10.1002/anie.201310843 – ident: e_1_2_10_3_1 doi: 10.1016/j.trsl.2020.02.008 – ident: e_1_2_10_18_1 doi: 10.1002/cmdc.202000726 – ident: e_1_2_10_26_1 doi: 10.1021/jacs.1c00076 – ident: e_1_2_10_22_1 doi: 10.1002/cmdc.202200486 – ident: e_1_2_10_4_1 doi: 10.1038/ja.2017.117 – ident: e_1_2_10_41_1 doi: 10.1021/acsinfecdis.1c00158 – ident: e_1_2_10_25_1 doi: 10.2741/Wright – ident: e_1_2_10_33_1 doi: 10.1038/ng0793-289 – ident: e_1_2_10_6_1 doi: 10.1039/C5MD00384A – ident: e_1_2_10_12_1 doi: 10.1016/j.cmi.2020.12.004 – ident: e_1_2_10_34_1 doi: 10.1073/pnas.0811258106 – ident: e_1_2_10_10_1 doi: 10.1016/j.ebiom.2021.103652 – ident: e_1_2_10_17_1 doi: 10.1021/jacs.9b11601 |
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| Snippet | We report the synthesis and evaluation of two new apramycin 5‐O‐β‐d‐ribofuranosides, or apralogs, carrying aminoalkyl branches at the ribofuranose 4‐position.... We report the synthesis and evaluation of two new apramycin 5‐ O ‐β‐ d ‐ribofuranosides, or apralogs, carrying aminoalkyl branches at the ribofuranose... |
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| SubjectTerms | aminoglycoside modifying enzymes Aminoglycoside phosphotransferase Aminoglycosides Antibacterial activity antibacterial agents antiribosomal activity Apramycin glycosides glycosylation Pathogens Phosphotransferase Protein biosynthesis Protein synthesis Ribose Ribosomes |
| Title | Synthesis and Evaluation of Novel 5‐O‐(4‐C‐Aminoalkyl‐β‐D‐ribofuranosyl) Apramycin Derivatives for the Inhibition of Gram‐Negative Pathogens Carrying the Aminoglycoside Phosphotransferase(3′)‐Ia Resistance Determinant |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fhlca.202300138 https://www.proquest.com/docview/2894048156 |
| Volume | 106 |
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