Synthesis and Biological Evaluation of New Hydrazone Derivatives of Quinoline and Their Cu(II) and Zn(II) Complexes againstMycobacterium tuberculosis

Mandewale, Mustapha C.; Thorat, Bapu R.; Shelke, Dnyaneshwar; Yamgar, Ramesh

doi:10.1155/2015/153015

Cited by 46 publications

(25 citation statements)

References 18 publications

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“…Our results of the copper(II) complexes loaded into the NLCs showed better tuberculostatic activity against M. tuberculosis H 37 R v than the values reported by Mandewale et al,48 wherein the copper(II) complexes bound to hydrazone ligands showed MIC values ranging from 6.25–12.5 μg/mL and the free ligands displayed MIC values from 25–50 μg/mL.…”

Section: Resultssupporting

confidence: 51%

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

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: Resultssupporting

confidence: 51%

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

Sato

Oshiro

Machado

et al. 2017

DDDT

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“…Additionally, quinolines are considered as an interesting group of compounds, many of which have widespread pharmacologicalactions such as anti-microbial, [1][2][3][4] anti-inflammatory, [5][6][7][8] antitubercular, [9][10][11][12] anti-convulsant, [13] antihypertensive, [14,15] antioxidant, [16][17][18][19] and anticancer [20] activities. Nitrones can release nitric oxide in larger amounts compared to corresponding oximes.…”

mentioning

confidence: 99%

“…actions such as anti-microbial, [1][2][3][4] anti-inflammatory, [5][6][7][8] antitubercular, [9][10][11][12] anti-convulsant, [13] antihypertensive, [14,15] antioxidant, [16][17][18][19] and anticancer [20] activities. Several mechanisms can explain the anticancer effect of quinoline derivatives including: topoisomerase inhibition, [21][22][23] DNA intercalation, [24] protein kinases inhibition, [25][26][27] tubulin polymerase inhibition, [28][29][30][31] and induction of apoptosis.…”

mentioning

confidence: 99%

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Abdelbaset

Abdel‐Aziz

Abuo‐Rahma

et al. 2018

Arch. Pharm. Chem. Life Sci.

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Novel quinoline derivatives carrying nitrones and oxime as nitric oxide donors were prepared and characterized using different spectroscopic techniques. Nitrones can release nitric oxide in larger amounts compared to corresponding oximes. Antiproliferative screening results showed that the 2-benzylthioquinoline nitrones 6e and 6f and the 2-methylthio analogues 6g and 6h exhibited promising antiproliferative activity especially against leukemia and colon cancer cell lines. Compounds 6c, 6e, and 6f exhibited higher potency as anticancer agents compared to doxorubicin, with IC 50 ranging from 0.45 to 0.91 μM. A remarkable overexpression of caspase-3 protein levels was observed in cells treated with the tested compounds. Compound 6e exhibited more pre-G1 apoptosis and cell cycle arrest at the G2/M phase than in other phases.These results revealed that the tested compounds can cause programmed cell death through overexpression of caspase 3, which may be attributed to the release of nitric oxide. K E Y W O R D S antiproliferative, apoptosis, caspase 3, nitric oxide, nitrones, oximes 1 | INTRODUCTION Quinoline is a significant nucleus which has attracted the attention of medicinal chemists due to its variable pharmacological activities. Easy functionalization of various ring positions of quinoline makes it an attractive synthetic building block for design and synthesis of new drugs. Additionally, quinolines are considered as an interesting group of compounds, many of which have widespread pharmacologicalactions such as anti-microbial, [1][2][3][4] anti-inflammatory, [5][6][7][8] antitubercular, [9][10][11][12] anti-convulsant, [13] antihypertensive, [14,15] antioxidant, [16][17][18][19] and anticancer [20] activities. Several mechanisms can explain the anticancer effect of quinoline derivatives including: topoisomerase inhibition, [21][22][23] DNA intercalation, [24] protein kinases inhibition, [25][26][27] tubulin polymerase inhibition, [28][29][30][31] and induction of apoptosis. [32,33] Quinoline derivative I exhibited potent anticancer activity against brain cancer cell line U87 with IC 50 of 1.5 nM. [31] Compound II exhibits remarkable anticancer activity against HL60 cancer cell line with IC 50 of 0.68 μM (Figure 1). [33] Incorporation of biologically active moieties into quinoline such as nitrones [34] and oximes [35] may produce biologically active anticancer agents.Compound III showed significant anticancer activity with IC 50 of 31.42 μM against Hep-G 2 cancer cell line (Figure 1). [34] Nitrones are a Arch Pharm Chem Life Sci. 2019;352:e1800270.wileyonlinelibrary.com/journal/ardp

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“…This causes an increase in -electron delocalization throughout the coordination ring. This results in increased metal complex lipophilicity [56]. Therefore, research on flavonoid metal complexes is very helpful in developing new TB drugs.…”

Section: Bioinorganic Chemistry Associated With Radical Scavenging Acmentioning

confidence: 99%

Bioinorganic Chemistry and Computational Study of Herbal Medicine to Treatment of Tuberculosis

Widyarti¹,

Kamaruddin²,

Aristyani³

et al. 2020

Medicinal Plants - Use in Prevention and Treatment of Diseases

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Tuberculosis (TB) is one of the leading infectious diseases in the world. The disease is commonly caused by Mycobacterium tuberculosis (Mtb) bacteria which are capable of rapidly spreading through droplet transmission. In developing countries, poverty and malnutrition cause immunodeficiency which is considered as the main risk factor for the incidence of TB. Treatment of TB has been proven to be difficult because treatment options are very limited and found to be expensive specifically in developing countries. Moreover, the existence of extensively drug-resistant TB phenomena is frequently happening in these countries because of mishandling treatments used for this disease. In Indonesia, the traditional herbal medicine, namely, jamu, has been utilized since a long time ago to treat diseases including TB. The present study by using computational methods found that there are many active compounds that can bound and influence proteins responsible for TB pathogenesis. Besides, these compounds have the potency to modulate the host immune system. The current chapter discussed the possible interaction of the antioxidant compounds with the chelating potential to form a complex with transitional metal as the central atom. In the perspective of bioinorganic chemistry, this complex has a scavenging activity which is expected to have a role in overcoming energy management of the host cell during infection pathogenesis. It is important to involve bioinorganic chemistry in energy management during infection, correlated with impairing of niacin metabolism of the host cell in which the host cell mitochondria cannot competitively gain free radicals during infection. This phenomenon is the main reason to propose herbal medicine as a source of niacin and provide a proper environment for gastrointestinal commensal microbiota to treat and govern protection from TB infection.

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Synthesis and Biological Evaluation of New Hydrazone Derivatives of Quinoline and Their Cu(II) and Zn(II) Complexes againstMycobacterium tuberculosis

Cited by 46 publications

References 18 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>

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Bioinorganic Chemistry and Computational Study of Herbal Medicine to Treatment of Tuberculosis

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