Bacterial Reduction as Means for Colonic Drug Delivery: Can Other Chemical Groups Provide an Alternative to the Azo Bond?

Saphier, Sigal; Haft, Avital; Margel, Shlomo

doi:10.1021/jm301381a

Cited by 21 publications

(16 citation statements)

References 32 publications

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“…8 Azobenzenes display a reversible isomerization between trans and cis isomers by diverse stability and this feature is used in the development of photomechanical processes and medical fields. [9][10][11] Heterocyclic moieties, such as pyridine have been utilized for the synthesis of new azo dyes to enhance their color strength and brilliant shades. 12,13 Azo pyridine derivatives have a wide range of biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

et al. 2018

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The reaction of 2-hydroxy-5-(pyridine-4-yldiazenyl)benzaldehyde with n-alkyl bromides generated five novel azo pyridinium salts in good to excellent yields. The 1 H and 13 C NMR and UV-Vis absorption spectra indicated several tautomers for the new compounds. The NMR, UV-Vis absorption spectra and quantum chemical calculations show that the azo pyridinium salts have a new resonant structure compared to the corresponding azo precursor. Antibacterial activity was studied by disc diffusion and MIC methods. Diphenylpicrylhydrazyl (DPPH) assay was used to determine the antioxidant properties. The effects of carbon chain length on antimicrobial activity were also investigated. The results showed that existence of alkyl groups is crucial for the antibacterial properties. The new compound with decyl group displayed the best antibacterial activity. prepared and purified according to the method reported in the literature. 19 Melting points were measured on an Electrothermal 9200 apparatus. Mass spectra were recorded on an Agilent MS Model 5973. FT-IR spectra were recorded on a Shimadzu 8400S spectrometer using KBr disc. The electronic absorption spectra were recorded with a Shimadzu 1650 spectrophotometer. 1 H and 13 C NMR spectra were recorded in DMSO-d 6 as the solvent on the Bruker DRX-300 MHz and 400 MHz Advance spectrometers.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

et al. 2018

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“…( 30 ) A well-known example of azo reduction is the prodrug sulfasalazine, which releases 5-aminosalicylic acid (5-ASA) in response to azo reduction in the gut and is considerably applied in the treatment of IBD. ( 31 ) In a recent study by Qiao et al ( 32 ), an amphiphilic polycurcumin (PCur) composed of hydrophilic PEG and hydrophobic curcumin with disulfide, was designed in response to the bacterial reduction in colon. GSH was used to stimulate reduced levels in vitro condition.…”

Section: Stimuli Responsive Nanoparticles Of Natural Products For Drumentioning

confidence: 99%

A systematic review of nano formulation of natural products for the treatment of inflammatory bowel disease: drug delivery and pharmacological targets

et al. 2018

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Inflammatory bowel diseases (IBD), which is classified into Crohn’s disease and ulcerative colitis, are among chronic gastrointestinal diseases with unknown pathogenesis. Diverse strategies have been applied for the treatment of this chronic disease. However, selective and site-specific routes of drug delivery to the inflamed location of the colon remain of high importance. Consequently, the application and effects of natural products in the form of nanoformulation and stimuli responsive nanoparticles as a novel strategy for the treatment of IBD are discussed in this review article. This approach may potentially overcome some complications that are associated with conventional means of colon drug delivery. Meanwhile, in vitro and in vivo studies pave the way for understanding of the mechanism that lies behind this chronic relapsing disease and potentially more effective treatment. Graphical abstractᅟ

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“…Moreover, rat cecal suspension from anaerobic cultures was prepared to evaluate the release of PCur in colonic reducing environment (Saphier et al, 2012). Sterilized cecal contents were also used as a control.…”

Section: In Vitro Release Study Of Pcur Conjugatementioning

confidence: 99%

Orally delivered polycurcumin responsive to bacterial reduction for targeted therapy of inflammatory bowel disease

et al. 2017

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Inflammatory bowel disease (IBD) such as Crohn's disease and ulcerative colitis is a chronic autoimmune disease affecting nearly five million people worldwide. Among all drug delivery system, oral administration is the most preferable route for colon-specific targeting and the treatment of IBD. Herein, an amphiphilic curcumin polymer (PCur) composed of hydrophilic poly(ethylene glycol) (PEG) and hydrophobic curcumin (Cur) linked by disulfide bond was synthesized and characterized. The sufficient solubility, nano-scaled size and close to the neutral surface potential of PCur lead to preferential accumulation of the active drug in the inflamed regions of the gut. Moreover, PCur showed limited drug release and enhanced robustness under the physiological pH of the gastrointestinal tract (GIT), and a significantly elevated release was observed when responding to a bacterial reduction in the colon. Furthermore, cellular studies confirmed PCur had low cytotoxicity and increased transmembrane permeability, resulting in improved oral bioavailability evidenced by in vivo pharmacokinetics of rats. Finally, with DSS-induced murine model of IBD, we demonstrated that orally administered PCur ameliorated the inflammatory progression in the colon and could protect mice from IBD. In conclusion, it is illustrated that the developed PCur conjugate could potentially be employed as a colon-specific candidate for IBD treatment.

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Bacterial Reduction as Means for Colonic Drug Delivery: Can Other Chemical Groups Provide an Alternative to the Azo Bond?

Cited by 21 publications

References 32 publications

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

A systematic review of nano formulation of natural products for the treatment of inflammatory bowel disease: drug delivery and pharmacological targets

Orally delivered polycurcumin responsive to bacterial reduction for targeted therapy of inflammatory bowel disease

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