Anti-mycobacterial activities of copper(II) complexes. Part II. Lipophilic hydroxypyridinones derived from maltol

Salsbury, Lauren E.; Robertson, Katherine N.; Flewelling, Andrew J.; Li, Hoaxin; Geier, Stephen J.; Vogels, Christopher M.; Gray, Christopher A.; Westcott, Stephen A.

doi:10.1139/cjc-2014-0426

Cited by 10 publications

(7 citation statements)

References 45 publications

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“…Salsbury et al13 showed that copper(II) complexes containing lipophilic hydroxypyridinone-derived ligands (2a and 2h) exhibited considerable antimicrobial activity against M. tuberculosis H 37 R a with a minimum inhibitory concentration (MIC) of 12.50 μg/mL for both complexes. In addition, Hoffman et al14 demonstrated that copper(II) pyrophosphate complexes [Cu(phen)(H 2 O)(H 2 P 2 O 7 )] (phen =1,10′-phenanthroline) showed promising antimicrobial activity against M. tuberculosis H 37 R v with an MIC of 31.25 μg/mL.…”

Section: Introductionmentioning

confidence: 99%

Nanostructured lipid carriers for incorporation of copper(II) complexes to be used against <em>Mycobacterium tuberculosis</em>

Sato

Oshiro

Machado

et al. 2017

DDDT

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Tuberculosis (TB) is a disease caused by Mycobacterium tuberculosis. Cessation of treatment before the recommended conclusion may lead to the emergence of multidrug-resistant strains. The aim of this study was to develop nanostructured lipid carriers (NLCs) for use in the treatment of M. tuberculosis. The NLCs comprised the following lipid phase: 2.07% polyoxyethylene 40 stearate, 2.05% caprylic/capric triglyceride, and 0.88% polyoxyl 40 hydrogenated castor oil; the following aqueous phase: 3.50% poloxamer 407 (F1–F6), and 0.50% cetyltrimethylammonium bromide (F7–F12); and incorporated the copper(II) complexes [CuCl2(INH)2]·H2O (1), [Cu(NCS)2(INH)2]·5H2O (2), and [Cu(NCO)2(INH)2]·4H2O (3) to form compounds F11.1, F11.2, and F11.3, respectively. The mean diameter of F11, F11.1, F11.2, and F11.3 ranged from 111.27±21.86 to 134.25±22.72 nm, 90.27±12.97 to 116.46±9.17 nm, 112.4±10.22 to 149.3±15.82 nm, and 78.65±6.00 to 122.00±8.70 nm, respectively. The polydispersity index values for the NLCs ranged from 0.13±0.01 to 0.30±0.09. The NLCs showed significant changes in zeta potential, except for F11.2, with F11, F11.1, F11.2, and F11.3 ranging from 18.87±4.04 to 23.25±1.13 mV, 17.03±1.77 to 21.42±1.87 mV, 20.51±1.88 to 22.60±3.44 mV, and 17.80±1.96 to 25.25±7.78 mV, respectively. Atomic force microscopy confirmed the formation of nanoscale spherical particle dispersions by the NLCs. Differential scanning calorimetry determined the melting points of the constituents of the NLCs. The in vitro activity of copper(II) complex-loaded NLCs against M. tuberculosis H37Rv showed an improvement in the anti-TB activity of 55.4, 27.1, and 41.1 times the activity for complexes 1, 2, and 3, respectively. An in vivo acute toxicity study of complex-loaded NLCs demonstrated their reduced toxicity. The results suggest that NLCs may be a powerful tool to optimize the activity of copper(II) complexes against M. tuberculosis.

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Section: Introductionmentioning

confidence: 99%

Nanostructured lipid carriers for incorporation of copper(II) complexes to be used against <em>Mycobacterium tuberculosis</em>

Sato

Oshiro

Machado

et al. 2017

DDDT

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“…A panel of probes was prepared where the Phe-residue in the tetrapeptide sequence central part (18,(21)(22), at the nitrogen-terminus (19) or the carbon-terminal lysine (20) was replaced by the dual fluorescent probe. A structural analog of 20 was represented by compound 23, where a protected Fechelating moiety (17) was incorporated into the structure. Compounds 26 and 27 were designed by the activation of the glutamic acid residue, which was orthogonally protected on the solid support for the selective conjugation of either 1°- (24) or 2°-amine (25) having HOPO (Fig.…”

Section: Sensing Of Iron In Living Systemsmentioning

confidence: 99%

Hydroxypyridinone based chelators: a molecular tool for fluorescence sensing and sensitization

Singh,

Kumari,

Kanungo

et al. 2024

Sens. Diagn.

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“…[9 -12] Ethyl maltol (1, 2-ethyl-3-hydroxy-4H-pyran-4-one, Figure 1) is the analog of maltol (I, 2-methyl-3-hydroxy-4H-pyran-4-one, Figure 1) and have similar biological activities to maltol. Maltol, a commercial natural metabolite, is primarily extracted from germinated seeds of Hordeum vulgare L. and Triticum aestivum L. [13] To the best of our knowledge, maltol is an excellent candidate for the study of antifungal activity, [14] anticancer activity, [15] anti-mycobacterial activity, [16] antioxidant activity, [17] neuroprotective effect, [18] and liver protection effect. [19] Moreover, maltol is used extensively as a food preservative, flavor-enhancing agent, and also in pharmaceutical and cosmetic formulations.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Oomycete Preliminary Mechanism of Sulfonate Derivatives of Ethyl Maltol

Che

Xing

Liu

et al. 2022

Chemistry & Biodiversity

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To discover novel molecules with unique mechanism against plant pathogenic oomycetes, sixteen new sulfonate derivatives of ethyl maltol (3a–p) were synthesized by structural modification of 2‐ethyl‐3‐hydroxy‐4H‐pyran‐4‐one, and their anti‐oomycete activity against a serious agricultural disease, Phytophthora capsici Leonian was determined in this study. Among all tested compounds, derivatives 3e, 3m and 3p exhibited the most potent anti‐oomycete activity against P. capsici with EC50 values of 19.40, 21.04 and 31.10 mg/L, respectively; especially 3e and 3m showed the best promising and pronounced anti‐oomycete activity than zoxamide (EC50=26.87 mg/L). The results further proved that 4‐tert‐butylphenylsulfonyl group, 3‐nitro‐4‐chlorophenylsulfonyl group and 8‐quinolinesulfonyl group introduced at the hydroxy position of ethyl maltol or maltol were necessary for obtaining the most potent compounds. Further mechanism studies of P. capsici treated with 3e demonstrated that this compound can affect the growth of mycelia by disrupting the integrity of the membrane, and the higher the concentration of the compound is, the greater the degree of membrane integrity damage. These important results will pave the way for further modification of ethyl maltol to develop potential new fungicides.

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Anti-mycobacterial activities of copper(II) complexes. Part II. Lipophilic hydroxypyridinones derived from maltol

Cited by 10 publications

References 45 publications

Nanostructured lipid carriers for incorporation of copper(II) complexes to be used against <em>Mycobacterium tuberculosis</em>

Nanostructured lipid carriers for incorporation of copper(II) complexes to be used against <em>Mycobacterium tuberculosis</em>

Hydroxypyridinone based chelators: a molecular tool for fluorescence sensing and sensitization

Synthesis and Anti‐Oomycete Preliminary Mechanism of Sulfonate Derivatives of Ethyl Maltol

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