{"id":1528,"date":"2025-02-22T15:06:31","date_gmt":"2025-02-22T13:06:31","guid":{"rendered":"https:\/\/www.technology-asgard.com\/?p=1528"},"modified":"2025-02-26T21:03:33","modified_gmt":"2025-02-26T19:03:33","slug":"analysis-of-aminoglycoside-modification-with-addition-of-oh-and-benzene-ring","status":"publish","type":"post","link":"https:\/\/www.technology-asgard.com\/en\/analysis-of-aminoglycoside-modification-with-addition-of-oh-and-benzene-ring\/","title":{"rendered":"Analysis of aminoglycoside modification with addition of -OH and benzene ring"},"content":{"rendered":"\n<p><strong>Analysis of aminoglycoside modification with addition of -OH and benzene ring<\/strong><br><br>This is a work, and the author&#8217;s right to a work under international law comes into force from the moment the work is created.<\/p>\n\n\n\n<p>The name of the new drug is Aminophenolazide<strong><\/strong><\/p>\n\n\n\n<p><strong>Author &#8211; Sukhachev Denis Pavlovich<\/strong><\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<p><strong>1. Initial structure of the aminoglycoside (before changes)<\/strong><\/p>\n\n\n\n<p><strong>Chemical structure:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>The basis of the molecule is an aminoglycoside ring containing several amino groups (-NH\u2082) and hydroxyl groups (-OH).<\/li>\n\n\n\n<li>This structure allows the molecule to interact with the 30S subunit of bacterial ribosomes, inhibiting protein synthesis.<\/li>\n\n\n\n<li>Sites that are targets for bacterial acetylation and phosphorylation enzymes are marked, which can lead to bacterial resistance.<\/li>\n<\/ul>\n\n\n\n<p><strong>Physical and chemical properties (subject to change):<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Hydrophilicity:<\/strong> High, which contributes to good solubility in water.<\/li>\n\n\n\n<li><strong>Lipophilicity:<\/strong> Low, which limits permeability through cell membranes.<\/li>\n\n\n\n<li><strong>Solubility:<\/strong> High in aqueous media, poor in organic solvents.<\/li>\n\n\n\n<li><strong>Enzyme resistance:<\/strong> Relatively low, as many bacterial strains produce acetyltransferases that modify the aminoglycoside and render it inactive.<\/li>\n\n\n\n<li><strong>Bioavailability:<\/strong> Good for intravenous and intramuscular administration, but poor for oral administration.<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<p><strong>2. Modified structure of the aminoglycoside (after changes)<\/strong><\/p>\n\n\n\n<p><strong>Changes have been made:<\/strong><\/p>\n\n\n\n<ol start=\"1\" class=\"wp-block-list\">\n<li><strong>Addition of a hydroxyl (-OH) group to O1<\/strong>\n<ul class=\"wp-block-list\">\n<li>This increases the hydrophilicity of the molecule.<\/li>\n\n\n\n<li>May affect interaction with bacterial ribosomes.<\/li>\n\n\n\n<li>It can protect the molecule from enzymatic degradation.<\/li>\n<\/ul>\n<\/li>\n\n\n\n<li><strong>Addition of a benzene ring to N1<\/strong>\n<ul class=\"wp-block-list\">\n<li>Changes the electronic configuration of a molecule.<\/li>\n\n\n\n<li>Makes the molecule more <strong>lipophilic<\/strong>, which can improve cell membrane penetration.<\/li>\n\n\n\n<li>It can <strong>protect the molecule from enzymatic degradation <\/strong>(bacterial acetyltransferases may not recognize this altered structure).<\/li>\n<\/ul>\n<\/li>\n<\/ol>\n\n\n\n<p><strong>Physical and chemical properties (after changes):<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Hydrophilicity:<\/strong> Moderately decreases (due to the benzene ring), but the -OH group compensates for this effect.<\/li>\n\n\n\n<li><strong>Lipophilicity:<\/strong> Increases due to the benzene ring, which can increase permeability through membranes.<\/li>\n\n\n\n<li><strong>Solubility:<\/strong> The balance between solubility in water and in organic solvents.<\/li>\n\n\n\n<li><strong>Enzyme resistance:<\/strong> Improved as modified sites may no longer be targets for bacterial acetyltransferases.<\/li>\n\n\n\n<li><strong>Bioavailability:<\/strong> Potentially improved, especially for tissue penetration.<\/li>\n<\/ul>\n\n\n\n<p><strong>Expected changes in biological activity:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>The ability to bind to ribosomes may decrease<\/strong>, which may affect antibacterial activity.<\/li>\n\n\n\n<li><strong>Membrane penetration may improve<\/strong>, which can be useful against Gram-negative bacteria.<\/li>\n\n\n\n<li><strong>It may be effective against resistant strains of bacteria <\/strong>that have acetyltransferases.<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<p><strong>3. How to achieve this modification in the laboratory?<\/strong><\/p>\n\n\n\n<p><strong>3.1 Addition of -OH group to O1 (Hydroxylation)<\/strong><\/p>\n\n\n\n<p><strong>Methods:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Use of reagents for selective oxidation (e.g., reaction with sodium periodate NaIO\u2084).<\/li>\n\n\n\n<li>Or enzymatic introduction of a hydroxyl group using oxygenases.<\/li>\n<\/ul>\n\n\n\n<p><strong>Terms:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Controlling the pH (~7-8) to avoid aminoglycoside degradation.<\/li>\n\n\n\n<li>The temperature is 25-40\u00b0C.<\/li>\n\n\n\n<li>An organic solvent can be used to selectively modify certain groups.<\/li>\n<\/ul>\n\n\n\n<p><strong>3.2 Addition of a benzene ring to N1 (Acylation or Alkylation)<\/strong><\/p>\n\n\n\n<p><strong>Methods:<\/strong><\/p>\n\n\n\n<ol start=\"1\" class=\"wp-block-list\">\n<li><strong>Acylation <\/strong>(via amide bond)\n<ul class=\"wp-block-list\">\n<li>Use of benzoyl chloride (C\u2086H\u2085COCl) in the presence of a base (e.g., pyridine).<\/li>\n\n\n\n<li>A benzoyl-N1-substituted aminoglycoside is formed.<\/li>\n<\/ul>\n<\/li>\n\n\n\n<li><strong>Alkylation <\/strong>(through direct replacement of hydrogen with a benzyl group)\n<ul class=\"wp-block-list\">\n<li>The use of benzyl bromide (C\u2086H\u2085CH\u2082Br) in the presence of a weak base (NaHCO\u2083).<\/li>\n\n\n\n<li>A catalyst (Pd\/C) can be used to form more stable bonds.<\/li>\n<\/ul>\n<\/li>\n<\/ol>\n\n\n\n<p><strong>Terms:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>pH 8-10 (to avoid unwanted side effects).<\/li>\n\n\n\n<li>The temperature is ~50\u00b0C.<\/li>\n\n\n\n<li>Reaction time: 2-6 hours.<\/li>\n<\/ul>\n\n\n\n<p><strong>3.3 Cleaning and checking the modification<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Use of <strong>chromatography (HPLC<\/strong>) to confirm changes.<\/li>\n\n\n\n<li><strong>NMR spectroscopy <\/strong>(nuclear magnetic resonance) to verify the structure.<\/li>\n\n\n\n<li>Testing of <strong>antibacterial activity <\/strong>on bacterial cultures.<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<p><strong>4. 4. Conclusions and further research<\/strong><\/p>\n\n\n\n<p><strong>What did we get?<\/strong><\/p>\n\n\n\n<ol start=\"1\" class=\"wp-block-list\">\n<li><strong>Increased lipophilicity <\/strong>\u2192 potentially better membrane penetration.<\/li>\n\n\n\n<li><strong>Protection against bacterial enzymes <\/strong>\u2192 possible activity against resistant strains.<\/li>\n\n\n\n<li><strong>Modified bioavailability <\/strong>\u2192 potentially changes in pharmacokinetics.<\/li>\n<\/ol>\n\n\n\n<p><strong>What do you need to check?<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Does the antibacterial activity remain after the changes?<\/li>\n\n\n\n<li>Does the new molecule cause toxic effects?<\/li>\n\n\n\n<li>Is it possible to scale up the synthesis in an industrial setting?<\/li>\n<\/ul>\n\n\n\n<p>If you need to develop a more detailed laboratory protocol or test the effectiveness of a modified antibiotic on certain bacteria, I can help you with that! \ud83d\ude80<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Analysis of aminoglycoside modification with addition of -OH and benzene ring This is a work, and the author&#8217;s right to a work under international law comes into force from the moment the work is created. The name of the new drug is Aminophenolazide Author &#8211; Sukhachev Denis Pavlovich 1. Initial structure of the aminoglycoside (before changes) Chemical structure: Physical and chemical properties (subject to change): 2. Modified structure of the aminoglycoside (after changes) Changes have been made: Physical and chemical [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":1509,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[26],"tags":[],"class_list":["post-1528","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-medical-research"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v24.3 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Analysis of aminoglycoside modification with addition of -OH and benzene ring - Asgard Technology<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.technology-asgard.com\/en\/analysis-of-aminoglycoside-modification-with-addition-of-oh-and-benzene-ring\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Analysis of aminoglycoside modification with addition of -OH and benzene ring - Asgard Technology\" \/>\n<meta property=\"og:description\" content=\"Analysis of aminoglycoside modification with addition of -OH and benzene ring This is a work, and the author&#8217;s right to a work under international law comes into force from the moment the work is created. 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