Antibacterial Activity of &amp;beta;-Cyclodextrin and 2-Hydroxypropyl-&amp;beta;-Cyclodextrin Trimethoprim Complexes

M.,

doi:10.3844/ajmsp.2011.1.8

American Journal of Microbiology

2011

DOI: 10.3844/ajmsp.2011.1.8

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Antibacterial Activity of β-Cyclodextrin and 2-Hydroxypropyl-β-Cyclodextrin Trimethoprim Complexes

M. M.¹

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Cited by 7 publications

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A Trimethoprim Conjugate of Thiomaltose Has Enhanced Antibacterial Efficacy In Vivo

et al. 2018

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Trimethoprim is one of the most widely used antibiotics in the world. However, its efficacy is frequently limited by its poor water solubility and dose limiting toxicity. Prodrug strategies based on conjugation of oligosaccharides to trimethoprim have great potential for increasing the solubility of trimethoprim and lowering its toxicity, but they have been challenging to develop due to the sensitivity of trimethoprim to chemical modifications, and the rapid degradation of oligosaccharides in serum. In this report, we present a trimethoprim conjugate of maltodextrin termed TM-TMP, which increased the water solubility of trimethoprim by over 100 times, was stable to serum enzymes, and was active against urinary tract infections in mice. TM-TMP is composed of thiomaltose conjugated to trimethoprim, via a self-immolative disulfide linkage, and releases 4′-OH-trimethoprim (TMP-OH) after disulfide cleavage, which is a known metabolic product of trimethoprim and is as potent as trimethoprim. TM-TMP also contains a new maltodextrin targeting ligand composed of thiomaltose, which is stable to hydrolysis by serum amylases and therefore has the metabolic stability needed for in vivo use. TM-TMP has the potential to significantly improve the treatment of a wide number of infections given its high water solubility and the widespread use of trimethoprim.

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A Trimethoprim Conjugate of Thiomaltose Has Enhanced Antibacterial Efficacy In Vivo

et al. 2018

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Thioamide Derivative of the Potent Antitubercular 2-(Decylsulfonyl)acetamide is Less Active Against Mycobacterium tuberculosis, but a More Potent Antistaphylococcal Agent

et al. 2018

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Due to the prevalence of thioamides in antibacterial compounds, we chose to convert the amide in the antitubercular compound 2-(decylsulfonyl)acetamide to a thioamide using Lawesson’s reagent to study its activity against a range of microorganisms. This derivative (8) had significantly diminished activity against tuberculosis but slightly better activity than the parent compound against the Gram positive species Staphylococcus aureus. This activity against a second major pathogen is remarkable considering the structural simplicity of these compounds.

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Spray dried nanospheres for inclusion complexes of cefpodoxime proxetil with β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and methyl-β-cyclodextrin: improved dissolution and enhanced antibacterial activity

Kırımlıoğlu

2021

Drug Development and Industrial Pharmacy

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Antibacterial Activity of β-Cyclodextrin and 2-Hydroxypropyl-β-Cyclodextrin Trimethoprim Complexes

Cited by 7 publications

References 14 publications

A Trimethoprim Conjugate of Thiomaltose Has Enhanced Antibacterial Efficacy In Vivo

A Trimethoprim Conjugate of Thiomaltose Has Enhanced Antibacterial Efficacy In Vivo

Thioamide Derivative of the Potent Antitubercular 2-(Decylsulfonyl)acetamide is Less Active Against Mycobacterium tuberculosis, but a More Potent Antistaphylococcal Agent

Spray dried nanospheres for inclusion complexes of cefpodoxime proxetil with β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and methyl-β-cyclodextrin: improved dissolution and enhanced antibacterial activity

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