Antimicrobial cationic polycarbonates

An antimicrobial and cationic polymer technology, applied in biocides, antibacterials, antifungals, etc.

Active Publication Date: 2015-11-25
IBM CORP +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, increasing hydrophobicity in an effort to increase activity often proves problematic due t

Method used

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  • Antimicrobial cationic polycarbonates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 10

[0654] The preparation of Example 10 is representative. The cationic polymer was prepared according to the reaction sequence in Scheme 1.

[0655] plan 1.

[0656]

[0657] Part 1. In an inert glove box, a vial was charged with Chol-OPr-OH (0.179 g, 0.4 mmol), TU (0.04 g, 0.1 mmol), MTC-BnCl (0.6 g, 2 mmol), dichloromethane ( DCM) (3 g) and stir bar. The reaction mixture was stirred and polymerization was started by addition of DBU (20 μL, 0.15 mmol). After 15 minutes, excess acetyl chloride was added to quench the reaction and acetylate the end of IP-1 to form IP-2. Precipitation of the acetylated intermediate polymer IP-2 into isopropanol gave 0.73 g (94%) of white waxy polymer. use 1 HNMR (CDCl 3 ) and GPC (THF, 37°C) to characterize the polymer. Through the carbonate doublet (2H, -OCOOCH 2 -, 4.7ppm) disappear and include the newly formed linear carbonate methylene (-CH 2 OCOOCH 2 -) and the corresponding appearance of a broad multiplet (6H, 4.2 ppm) for both ...

Embodiment 28-41

[0667] Examples 28-41. Using 4-methylbenzyl alcohol (4-MeBnOH) as an initiator, MTC-BnCl, MTC-PrCl or MTC-PrBr as a cyclic carbonate monomer, and various amine quaternizers Cationic polymers were prepared according to the general polymerization and quaternization procedures above.

[0668] Table 8 lists cationic homopolymers prepared using 4-MeBnOH initiator, their degree of polymerization (DP), quaternizing agent, CMC, and the total number of carbons of each cationic repeat unit.

[0669] Table 8.

[0670]

[0671] a "None" means that the terminal hydroxyl groups of the polycarbonate chain are not protected.

[0672] b N.D. means not determined.

[0673] c actual, as by 1 determined by HNMR analysis

[0674] C. Cationic random copolymer prepared with MTC-VitE having side chain α-tocopheryl moieties

Embodiment 42-50

[0675] Examples 42-50. Using MTC-PrBr and MTC-BnCl precursors for the cationic carbonate repeat unit, MTC-VitE as the hydrophobic comonomer, benzyl alcohol (BnOH) initiator, and DBU / Preparation of random cationic copolymers with thiourea. Quaternization with trimethylamine or N-substituted imidazoles. The reaction sequence is shown in Scheme 2.

[0676] Scenario 2.

[0677]

[0678] Example 50 is representative. MTC-BnCl (608.8 mg, 2.04 mmol, 30 equiv), MTC-VitE (40.0 mg, 68 micromol, 1.0 equiv) and TU (25.2 mg, 68 mol, 1.0 eq) was dissolved in dichloromethane (3 mL). To this solution, BnOH (7.0 μl, 68 μmol, 1.0 equiv) was added followed by DBU (10.2 μl, 68 μmol, 1.0 equiv) to initiate polymerization. The reaction mixture was allowed to stir at room temperature for 20 minutes and quenched by adding excess (-20 mg) of benzoic acid. The mixture was then precipitated into ice-cold methanol (50 mL) and centrifuged at -5°C for 30 minutes. The resulting translucent oil wa...

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Abstract

Antimicrobial cationic polymers having one or two cationic polycarbonate chains were prepared by organocatalyzed ring opening polymerization. One antimicrobial cationic polymer has a polymer chain consisting essentially of cationic carbonate repeat units linked to one or two end groups. The end groups can comprise a covalently bound form of biologically active compound such as cholesterol. Other antimicrobial cationic polymers have a random copolycarbonate chain comprising a minor mole fraction of hydrophobic repeat units bearing a covalently bound form of a vitamin E and/or vitamin D2. The cationic polymers exhibit high activity and selectivity against Gram-negative and Gram-positive microbes and fungi.

Description

[0001] Parties to a joint research agreement [0002] This invention was made pursuant to a joint research agreement between International Business Machines Corporation and the Agency For Science, Technology and Research, Singapore. Background technique [0003] The present invention relates to antimicrobial cationic polycarbonate polymers, and more particularly, to cationic polycarbonate homopolymers and random copolymers having 85 mole percent to 100 mole percent cationic carbonate repeat units. [0004] The ever-increasing presence of antibiotic-resistant bacteria has created an urgent need to develop new antibiotics. Antimicrobial peptides have high activity, biocompatibility and excellent selectivity. However, although more than 1000 antimicrobial peptides have been identified, only four peptides have successfully entered phase III clinical trials for wound healing. The main reasons for their extremely limited use arise from challenging synthesis, high construction cost...

Claims

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Application Information

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IPC IPC(8): A61K31/785A61K31/80
CPCA61K31/785A61K31/80C08G64/0241A01N33/12A61P31/04A61P31/10Y02A50/30A01N25/10
Inventor D.J.科迪R.A.迪彼得罗A.C.恩格勒J.L.赫德里克W.钦A.L.Z.李V.W.L.恩吉Z-Y.翁格Y.Y.杨
Owner IBM CORP
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