Targeted modifications of neomycin and paromomycin: Towards resistance-free antibiotics?

Obszynski, Julie; Loidon, H.; Blanc, Aurélien; Weibel, Jean‐Marc; Pale, Patrick

doi:10.1016/j.bioorg.2022.105824

Cited by 11 publications

(10 citation statements)

References 116 publications

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“…1 H NMR (300 MHz, CDCl 3 ) δ 7.27 (s, 10H), 6.17 (s, 1H), 5.55 (s, 1H), 4.64−4.60 (m, 6H), 4.49 (s, 1H), 4.40 (t, J = 3.7 Hz, 2H), 2.60 (s, 3H); 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ 215. 5, 137.3, 128.4, 127.9, 103.2, 73.9, 72.3, 71.7, 69.9, 68.4 6,8-Bis(benzyloxy)-2,4,10-trioxaadamantane (6). Hypophosphorous acid (50 wt % in H 2 O, 322.4 mg, 4.89 mmol) was added to a solution of 5 (450.0 mg, 0.98 mmol), triethylamine (1.09 g, 1.5 mL, 10.8 mmol), and 1,4-dioxane (3.3 mL).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…DOIA is also present in a group of aminoglycoside antibiotics, inosamycins, and is the biosynthetic precursor of 2-deoxystreptamine (DOS), the aglycone of several clinically important antibiotics, such as gentamicin, kanamycin, and neomycin . Recently, these aminoglycosides have been found to be effective inhibitors of heptosyltransferase I, critical to the biosynthesis of lipopolysaccharides present on bacterial cell surfaces, and modifications on the aminoglycosides have been disclosed as a promising way to yield new antibiotics . Preliminary study on nabscessins A and B also showed that they possess moderate antimicrobial activity against Cryptococcus neoformans .…”

Section: Introductionmentioning

confidence: 99%

“…4 Recently, these aminoglycosides have been found to be effective inhibitors of heptosyltransferase I, critical to the biosynthesis of lipopolysaccharides present on bacterial cell surfaces, 5 and modifications on the aminoglycosides have been disclosed as a promising way to yield new antibiotics. 6 Preliminary study on nabscessins A and B also showed that they possess moderate antimicrobial activity against Cryptococcus neoformans. 1a The potential of the nabscessins as new antibiotics has focused attention on their synthesis.…”

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Enantioselective Synthesis of Nabscessin C

Yeh,

Feng,

Chen

et al. 2023

J. Org. Chem.

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Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Enantioselective Synthesis of Nabscessin C

Yeh,

Feng,

Chen

et al. 2023

J. Org. Chem.

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“…Paromomycin is a water‐soluble broad‐spectrum aminoglycoside antibiotic derived from S. rimosus var . paromomycinus , which is structurally related to neomycin (neomycin has a 6′‐amino group, paromomycin has a 6′‐hydroxyl; Obszynski et al., 2022). The antibacterial properties of paromomycin are also similar to neomycin.…”

Section: Short Examples Of Riboswitch Biosensingmentioning

confidence: 99%

Advances in riboswitch‐based biosensor as food samples detection tool

Khan

Sun

et al. 2022

Comp Rev Food Sci Food Safe

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Food safety has always been a hot issue of social concern, and biosensing has been widely used in the field of food safety detection. Compared with traditional aptamer-based biosensors, aptamer-based riboswitch biosensing represents higher precision and programmability. A riboswitch is an elegant example of controlling gene expression, where the target is coupled to the aptamer domain, resulting in a conformational change in the downstream expression domain and determining the signal output. Riboswitch-based biosensing can be extensively applied to the portable real-time detection of food samples. The numerous key features of riboswitch-based biosensing emphasize their sustainability, renewable, and testing, which promises to transform engineering applications in the field of food safety. This review covers recent developments in riboswitch-based biosensors. The brief history, definition, and modular design (regulatory mode, reporter, and expression platform) of riboswitch-based biosensors are explained for better insight into the design and construction. We summarize recent advances in various riboswitch-based biosensors involving theophylline, malachite green, tetracycline, neomycin, fluoride, thrombin, naringenin, ciprofloxacin, and paromomycin, aiming to provide general guidance for the design of riboswitch-based biosensors. Finally, the challenges and prospects are also summarized as a way forward stratagem and signs of progress.

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“…After enzymic modification, the resulting products decrease or lose their affinity to the drug target and then decrease or lose their antibacterial activity. To tackle this problem, proactive structural modification on these drugs have been extensively investigated [ 4 , 5 , 6 , 7 ]. Through chemical modification, some sensitive groups on the drug molecules are eliminated or masked.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Bioassay of 2′-Modified Kanamycin A

Yan

Liu

et al. 2022

Molecules

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Chemical modification of old drugs is an important way to obtain new ones, and it has been widely used in developing new aminoglycoside antibiotics. However, many of the previous modifying strategies seem arbitrary for their lack of support from structural biological detail. In this paper, based on the structural information of aminoglycoside and its drug target, we firstly analyzed the reason that some 2′-N-acetylated products of aminoglycosides caused by aminoglycoside-modifying enzyme AAC(2′) can partially retain activity, and then we designed, synthesized, and evaluated a series of 2′-modified kanamycin A derivatives. Bioassay results showed our modifying strategy was feasible. Our study provided valuable structure–activity relationship information, which would help researchers to develop new aminoglycoside antibiotics more effectively.

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Targeted modifications of neomycin and paromomycin: Towards resistance-free antibiotics?

Cited by 11 publications

References 116 publications

Enantioselective Synthesis of Nabscessin C

Enantioselective Synthesis of Nabscessin C

Advances in riboswitch‐based biosensor as food samples detection tool

Design, Synthesis, and Bioassay of 2′-Modified Kanamycin A

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