International Business Machines Corporation

Agency for Science, Technology and Research

Coral Bay Ii, Llc.

Robert J Ono

James L Hedrick

Yi Yan Yang

Jeannette M Garcia

Ashlynn L Z Lee

Willy Chin

Qingxing Xu

Dylan J Boday

Rudy J Wojtecki

Mareva B Fevre

Mu San Zhang

Victor W L Ng

Julian M W Chan

Nor Lizawati Ibrahim

Gregory Breyta

Alshakim Nelson

Amanda Catherine Engler

Wei Han

Daniel Joseph Coady

Shrinivas Venkataraman

Jye Yng Teo

Chuan Yang

Wei Cheng

Zhi Xiang Voo

Shaoqiong Liu

Antimicrobial cationic polycarbonates and polyurethanes have been prepared comprising one or more pendent guanidinium and/or isothiouronium groups. Additionally, antimicrobial particles were prepared having a silica core linked to surface groups comprising a guanidinium and/or isothiouronium group. The cationic polymers and cationic particles can be potent antimicrobial agents against Gram-negative microbes, Gram-positive microbes, and/or fungi.

Antimicrobial guanidinium and thiouronium functionalized polymers

Methods, compounds, and compositions described herein generally relate to polyalkylamines and syntheses thereof. In some embodiments, a chemical compound has the formula:  Each instance of R is independently selected from the group consisting of aryl, alkyl, and polyether. Each instance of R' is independently selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, polyether, and alcohol. Each instance of Q and Z is independently a covalent bond or selected from the group consisting of alkyl and aralkyl.

Diamine dione polyalkyl amine synthesis

A number of cationic antimicrobial polymers have been synthesized by a condensation polymerization in bulk. The initial polymer formed has backbone tertiary nitrogens, which are subsequently quaternized using a suitable quaternizing agent (e.g., alkyl halide). The cationic polymers include polyamides, polycarbonates, polypolyureas and polyguanidiniums having a cationic repeat unit comprising the quaternary ammonium nitrogen as a backbone nitrogen. The cationic polymers can be active against Gram-negative, Gram-positive microbes, and/or fungi.

Condensation polymers for antimicrobial applications

Gel-forming block copolymers were prepared comprising i) a central hydrophilic block consisting essentially of a divalent poly(ethylene oxide) chain and ii) two peripheral monocarbonate or polycarbonate hydrophobic blocks linked to the central block by linking groups bearing one or more hydrogen bond forming *&#x2014;N(H)&#x2014;* groups. The hydrophobic blocks comprise one or more vitamin-bearing subunits. The gel-forming block copolymers can be used to prepare various biodegradable and/or biocompatible hydrogel and organogel drug compositions, in particular antimicrobial and/or anti-tumor drug compositions. The hydrogel compositions have utility in depot injections for drug delivery. The hydrogen bonding *&#x2014;N(H)&#x2014;* group(s) provide longer in vivo lifetime of the hydrogel before degradation and a more prolonged and controlled release rate of a hydrophobic drug compared to similar hydrogels prepared from poly(ethylene glycol).

Vitamin functionalized gel-forming block copolymers for biomedical applications

Eight-membered ring cyclic carbonates having an oxygen or an acylated nitrogen at position 6 were prepared by reaction of precursor diols with ethyl chloroformate. The cyclic carbonates undergo organocatalyzed ring opening polymerization. In one instance, the initial polymer formed comprises a carbonate repeat unit having a Boc-protected nitrogen in the polymer backbone. Deprotecting the nitrogen with acid forms a cationic carbonate repeat unit having a positive charged secondary ammonium nitrogen in the polymer backbone.

Cyclic carbonate monomers and ring opened polycarbonates therefrom

Thioaminal polymers are made from hexahydrotriazine precursors and dithiol precursors. The precursors are blended together and subjected to mild heating to make the polymers. An amine scavenger is used to remove amine byproducts from the reaction, thus promoting polymer growth to high molecular weight. The polymers have the general structure wherein each Ris independently an organic or hetero-organic group, a plurality of Rgroups are substituents having molecular weight greater than about 120 Daltons, and n is an integer greater than or equal to 1. The polymers may be functionalized by adding a thiol-reactive group to either end or both ends.

Amine scavengers for synthesis of polythioaminals

Cationic antimicrobial polymers have been synthesized by a bulk addition polymerization of a nucleophilic agent comprising two tertiary amines and an electrophilic agent that comprises two leaving groups and an aromatic ring between the leaving groups. The reaction solvent for the polymerization is chosen to allow precipitation of the cationic polymer at the polymerization temperature, thereby limiting molecular weight. Quaternization and polymerization occur concurrently. The cationic polymers can be highly active against Gram-negative and Gram-positive microbes, and/or fungi. The cationic polymers can also be non-hemolytic and non-cytotoxic at the effective concentration against the microbes.

Antimicrobial polymers formed by bulk polyaddition

Methods, compounds, and compositions described herein generally relate to polyalkylamines and syntheses thereof. In some embodiments, a chemical compound has the formula: Each instance of R is independently selected from the group consisting of aryl, alkyl, and polyether. Each instance of R' is independently selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, polyether, and alcohol. Each instance of Q and Z is independently a covalent bond or selected from the group consisting of alkyl and aralkyl.

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San Jose, CA, United States of America

Robert J Ono