Synthesis and Antimicrobial Evaluation of Amino Acid Naphthoquinone Derivatives as Potential Antibacterial Agents

Chemotherapy ◽  
2021 ◽  
Author(s):  
Lluvia Itzel López-López ◽  
Ernesto Rivera-Ávalos ◽  
Cecilia Villarreal-Reyes ◽  
Fidel Martínez-Gutiérrez ◽  
Denisse de Loera
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Amino Acid ◽  
Antimicrobial Activities ◽  
Biological Evaluation ◽  
Culture Collection ◽  
Anticancer Activities ◽  
Broth Microdilution Method

Background: The synthesis and biological evaluation of 1,4-naphthoquinone derivatives are of great interest since these compounds exhibit strong antibacterial, antifungal, antimalarial, and anticancer activities. The electronic properties of naphthoquinones are usually modulated by attaching functional groups containing nitrogen, oxygen and sulfur atoms, which tune their biological potency and selectivity. Methods: A series of 13 amino acid 1,4-naphthoquinone derivatives were synthesized under assisted microwave and ultrasound conditions. The antibacterial activity compounds was tested against American type Culture Collection (ATCC): Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Enterococcus faecalis, as well two multidrug resistant pathogens: Escherichia coli and Staphylococcus aureus from clinical isolated. Minimal inhibitory concentration (MIC) was determined using the broth microdilution method. Results: MIC of derivatives 4–11, 14 and 16 showed antimicrobial activity against gram-positive and gram-negative bacteria. Antimicrobial activities of the compounds 4–8 and 14 were ≤MIC 24.7 μg∙mL-1 against all the reference strain, even more the compound 6 showed the most potent activity with a MIC of 3.9 μg∙mL-1 on S. aureus. On the clinical isolated the compounds 7, 8 and 14 showed a MIC of 49.7 and 24.7 μg∙mL-1 against S. aureus y E. coli respectively. About ADME properties and Osiris analysis, the compounds 4-16 presented high gastrointestinal absorption and good characteristics for oral bioavailability and the compound 14 was the less toxic. Conclusion: amino acid 1,4-naphthoquinone derivatives showed good in vitro antibacterial activity against clinical strains, and modifications on C-3 with cloride atom enhanced the efficiency against same pathogens.

Ferrocene-Based Antibacterial Agents: Synthesis, Characterization, and Biological Evaluation of Metal (II) Complexes with Glycine-Derived Compounds

2011 ◽  
Vol 339 ◽  
pp. 317-320 ◽  
Author(s):  
Yu Ting Liu ◽  
Xiao Ming Sun ◽  
Da Wei Yin
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Antibacterial Agents ◽  
Salmonella Typhi ◽  
Biological Evaluation ◽  
Bacterial Strains ◽  
Gram Negative ◽  
And Staphylococcus Aureus

A series of Ferrocene Schiff bases derived from glycine and their cobalt (II), copper (II), nickel (II), and zinc (II) metal complexes have been synthesized and characterized by IR, 1H NMR, MS and elemental analysis, the results conformed well with expected structures. The synthesized ligands, along with their metal (II) complexes, were screened in vitro for their antibacterial activity against three Gram-negative (Escherichia coli, Pseudomonas aeruginosa, and Salmonella typhi) and two Gram-positive (Bacillus subtilis and Staphylococcus aureus) bacterial strains. The results showed that the metal (II) complexes are more potent in antibacterial activity against one or more species in comparison with those of uncomplexed ligands.

scholarly journals Synthesis and Biological Evaluation of Aminonaphthols Incorporated Indole Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-12 ◽  
Author(s):  
Saundane Anand Raghunath ◽  
Kirankumar Nandibeoor Mathada
Keyword(s):  
Radical Scavenging ◽  
Antitubercular Activity ◽  
Antimicrobial Activities ◽  
Biological Evaluation ◽  
Secondary Amines ◽  
Anticancer Activities ◽  
One Pot ◽  
Antioxidant Power ◽  
Mic Value

An efficient one pot condensation of naphthols (1), 2,5-disubstituted indole-3-carboxaldehydes (2), and secondary amines (3) has been achieved using dichloromethane as a solvent, stirring at room temperature. Some of the new [(disubstituted amino)(5-substituted 2-phenyl-1H-indol-3-yl)methyl]naphthalene-ols (4) derivatives were prepared in good yields. The significant features of this method are simple work-up procedure, inexpensive nontoxic solvent, shorter reaction times, and excellent product yields. The structures of newly synthesized compounds (4a–r) are confirmed by their elemental analysis, FTIR, 1H and 13C NMR, and mass spectral data. These compounds were screened for their in vitro antioxidant, antimicrobial, antitubercular, and anticancer activities. Among the synthesized compounds (4a–r), the compound 4e exhibited highest activity for radical scavenging and ferric ions reducing antioxidant power activities; compounds 4b, 4h, and 4k showed good metal chelating activity. Compounds 4n and 4q showed excellent antimicrobial activities with MIC value 08 µg/mL against tested strains. Compounds 4h, 4k, 4n, and 4q exhibited promising antitubercular activity with MIC value 12.5 µg/mL. Compounds 4k and 4q exhibited 100% cell lysis at concentration 10 µg/mL against MDA-MB-231 (human adenocarcinoma mammary gland) cell lines.

scholarly journals In vitro and in vivo evaluation of antibacterial activity of Bridelia ferruginea extracts on some clinical isolates

2018 ◽  
Vol 7 (4) ◽  
pp. 392-398
Author(s):  
B.T Yunana ◽  
◽  
B. B Bukar ◽  
J. C Aguiyi ◽  
◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Bark Extract ◽  
Root Extract ◽  
Root Bark ◽  
Zone Of Inhibition ◽  
Bridelia Ferruginea

The ethanol extracts of root, bark and leaf of Bridelia ferruginea was investigated for antibacterial activity against clinical isolate of Staphylococcus aureus and Escherichia coli. The extracts had significant antibacterial activity in vitro at concentration of 25 mg/ml, 50 mg/ml, 100 mg/ml and 200 mg/ml and in vivo at dose of 50 mg/kg and 100 mg/kg. The root extract in vitro had the highest zone of inhibition, followed by the bark extract for both Staphylococcus aureus and Escherichia coli. The concentration of 200 mg/ml had the highest zone of inhibition in vitro. The minimum inhibitory concentration (MIC) showed a decreasing inhibitory effect of the plant extracts for both Staphylococcus aureus and Escherichia coli as the concentration decreases with root having 3.125 mg/ml, bark having 6.25 mg/ml and leaf having 25 mg/ml for Staphylococcus aureus and Escherichia coli. Likewise, the minimum bactericidal concentration (MBC) showed decreasing bactericide effects with decrease concentration with root having 12.5 mg/ml, bark having 12.5 mg/ml and leaf having 25 mg/ml for Escherichia coli while root had 6.25mg/ml, bark had 12.5mg/ml and leaf had 25mg/ml for Staphylococcus aureus. The in vivo investigation showed that the root and bark extract exhibited antibacterial activity on both Staphylococcus aureus and Escherichia coli at doses of 100mg/kg and 50mg/kg; the root extract had higher activity than the bark and root/bark combined. The dose of 100 mg/kg had the highest colonies reduction for Staphylococcus aureus and Escherichia coli in vivo. Preliminary phytochemical screening of root, bark and leaves of Bridelia ferruginea revealed the presence of tannins, flavonoids, carbohydrates, cardiac glycoside (root, bark and leaves), saponins (root and bark). The presence of tannins, saponins, flavonoid, cardiac glycoside and carbohydrate in the bark and root extracts of the plant indicates that the bark and root extracts were pharmacological importance

Rosemary and Tea Tree Essential Oils Exert Antibiofilm Activities In Vitro against Staphylococcus aureus and Escherichia coli

2020 ◽  
Vol 83 (7) ◽  
pp. 1261-1267
Author(s):  
TING LIU ◽  
JINGFAN WANG ◽  
XIAOMAN GONG ◽  
XIAOXIA WU ◽  
LIU LIU ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Essential Oil ◽  
Biofilm Formation ◽  
Gas Chromatography Mass Spectrometry ◽  
Tea Tree ◽  
E Coli ◽  
Microdilution Method ◽  
Broth Microdilution Method

ABSTRACT The purpose of the present study was to determine the bioactive compounds in rosemary essential oil (REO) and tea tree essential oil (TEO) and to investigate their antibacterial and antibiofilm activities against Staphylococcus aureus and Escherichia coli in vitro. The MIC and MBC assays were performed to assess the antibacterial activity of these two EOs against S. aureus and E. coli with the broth microdilution method. A crystal violet assay was used to ascertain the effects of EOs on the biofilm formation of the test strains, and a tetrazolium bromide (MTT) assay was used to measure the level of inactivation of mature biofilms by EOs. Gas chromatography–mass spectrometry revealed 15 compounds in REO and 27 compounds in TEO, representing 97.78 and 98.13% of the total EO, respectively. Eucalyptol and α-pinene were found in high concentrations in REO, and the two major compounds in TEO were 4-terpineol and terpinolene. The MICs of REO for the two S. aureus and E. coli test strains were both 0.5 mg/mL, and the MICs of TEO for the two strains were both 0.25 mg/mL. Therefore, these EOs can significantly inhibit the formation of biofilms and induced morphological biofilm changes, as verified by scanning electron microscopy. Both EOs had destructive effects on the mature biofilm of the two test strains. TEO was more inhibitory than REO for biofilm formation by the two test strains. HIGHLIGHTS

scholarly journals ANTIBACTERIAL PHOTODYNAMIC THERAPEUTIC STUDIES OF METALLATED PORPHYRIN AGAINST CHRONIC WOUND COLONISING BACTERIAL ISOLATES

2021 ◽  
Vol 46 (2) ◽  
Author(s):  
O. B Daramola ◽  
A. A Olajide ◽  
N Torimiro ◽  
R. C George
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Chronic Wound ◽  
Antimicrobial Activities ◽  
Diffusion Method ◽  
In Vitro Toxicity ◽  
Resistant Bacteria ◽  
Drug Resistant ◽  
Bacterial Strains

Wound infections have become life threatening as a result of treatment failures caused by multi-drug resistant pathogens. The search for newer compounds potent against antibiotic resistant bacteria associated with wounds is crucial. Hence this study investigated the application of antibacterial photodynamic therapy using meso tetra-(4-phenyl) porphyrin (TPP), metallated with zinc, tin and silver (ZnTPP, SnTPP and AgTPP), meso tetra-(4-sulphonatephenyl) porphyrin (TPPS) and the corresponding metallo meso tetra-(4-sulphonatephenyl) porphyrin (MTPPS) as photosensitizers. The in-vitro toxicity and photo-toxicity properties on four chronic wound colonizing multi-drug resistant bacterial strains: Staphylococcus aureus, Klebsiella sp., Proteus sp., and Escherichia coli were assessed using agar well diffusion method. Photo-toxicity of the compounds was investigated using 100 Watt tungsten lamp. Inhibitory activity of porphyrins tested against these bacterial strains showed Staphylococcus aureus to have both lowest (11±0.0 mm) and highest (33±1.1 mm) susceptibility to SnTPPS and ZnTPPS respectively. The sequence of data also showed appreciable improvement in the antimicrobial activities of five metalloporphyrins (SnTPP, AgTPP, ZnTPPS, SnTPPS and AgTPPS) exposed to light rays than when tested against bacterial strains in dark condition. ZnTPPS exhibited the best activity with improved photo-toxic activities against all bacterial strains (Staphylococcus aureus 33±1.1 mm, Klebsiella sp. 32±0.7 mm, Proteus sp. 28±0.7 mm and Escherichia coli 30±1.4 mm) examined in this study.

scholarly journals Antimicrobial activities of widely consumed herbal tea’s alone or in combination with antibiotics: An in vitro study

2016 ◽  
Author(s):  
Mayram Tuysuz ◽  
Sibel Dosler ◽  
Ayse Seher Birteksoz Tan ◽  
Gulten Otuk
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
In Vitro Study ◽  
Antimicrobial Activities ◽  
Combination Studies ◽  
Kill Curve ◽  
Time Kill ◽  
Microbroth Dilution ◽  
Antagonistic Interactions

Background: Because of increasing antibiotic resistance, herbal teas are the most popular natural alternatives, which are gaining even more importance. We examined the antimicrobial activities of 31 herbal teas both alone and in combination with antibiotics or antifungals against the standard and clinical isolates of Pseudomonas aeruginosa, Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Enterococcus faecalis, methicillin susceptible/resistant Staphylococcus aureus and Candida albicans. Methods: The antimicrobial activities of the teas were determined by using the disk diffusion and microbroth dilution methods, and the combination studies were examined by using the microbroth checkerboard and time killing curve methods. Results: Rosehip, rosehip bag, pomegranate blossom, thyme, wormwood, mint, echinacea bag, cinnamon, black, and green teas were active against most of the studied microorganisms. In the combination studies, we characterized all the expected effects (synergistic, additive, and antagonistic) between the teas and the antimicrobials. While synergy was observed more frequently between ampicillin, ampicillin-sulbactam, or nystatine, and the various tea combinations, most of the effects between the ciprofloxacin, erythromycin, cefuroxime, or amikacin and various tea combinations, particularly rosehip, rosehip bag, and pomegranate blossom teas, were antagonistic. The results of the time kill curve analyses showed that none of the herbal teas were bactericidal in their usage concentrations; however, in combination they were. Discussion: Some herbal teas, particularly rosehip and pomegranate blossom should be avoided because of antagonistic interactions during the course of antibiotic treatment or should be consumed alone.

scholarly journals Synthesis of antibiotic loaded polylactic acid nanoparticles and their antibacterial activity against Escherichia coli O157:H7 and methicillin-resistant Staphylococcus aureus

Biomédica ◽  
2017 ◽  
Vol 37 (1) ◽  
pp. 11 ◽  
Author(s):  
Mónica Tatiana Herrera ◽  
Jhon Jhamilton Artunduaga ◽  
Claudia Cristina Ortiz ◽  
Rodrigo Gonzalo Torres
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Polylactic Acid ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Escherichia Coli O157 ◽  
Methicillin Resistant ◽  
E Coli

Introducción. Las nanopartículas poliméricas constituyen una herramienta nanotecnológica que podría ayudar a combatir los microorganismos patógenos que han desarrollado resistencia a los antibióticos convencionales.Objetivo. Sintetizar nanopartículas de ácido poliláctico cargadas con ofloxacina y vancomicina, y determinar su actividad antibacteriana frente a Escherichia coli O157:H7 y Staphylococcus aureus resistente a la meticilina (SARM).Materiales y métodos. Las nanopartículas de ácido poliláctico cargadas con ofloxacina y vancomicina se sintetizaron utilizando el método de emulsión y evaporación de solvente. Se caracterizaron mediante dispersión de luz en modo dinámico, electroforesis Doppler con láser y microscopía electrónica de barrido (S-TEM). Se evaluó la actividad antibacteriana in vitro de las nanopartículas de ácido poliláctico con ofloxacina contra E. coli O157:H7 y nanopartículas de ácido poliláctico con vancomicina contra SARM, mediante el método de microdilución en caldo.Resultados. Se obtuvieron nanopartículas poliméricas con tamaños inferiores a 379 nm y carga superficial positiva de hasta 21 mV. Las nanopartículas cargadas con ofloxacina presentaron una concentración inhibitoria mínima (CIM50) de 0,001 μg/ml frente a E. coli O157:H7, valor 40 veces menor que la concentración de antibiótico libre necesaria para lograr el mismo efecto (CIM50=0,04 μg/ml). Para SARM, las nanopartículas mejoraron la potencia farmacológica in vitro de la vancomicina alexhibir una MIC50 de 0,005 μg/ml, comparada con la de 0,5 μg/ml del antibiótico libre.Conclusiones. Se mejoró el efecto antibacteriano de la ofloxacina y la vancomicina incorporadas en la matriz polimérica de ácido poliláctico. Las nanopartículas poliméricas constituirían una alternativa para el control de cepas bacterianas de interés en salud pública.

scholarly journals A COMPARATIVE STUDY OF THE PHYTOCHEMICALS, ANTIOXIDANT AND ANTIBACTERIAL POTENTIAL OF METHANOLIC EXTRACTS OF TRICHOSANTHES CUCUMERINA (L.) VAR. CUCUMERINA UNDER IN VITRO CULTURE AND NATURAL CONDITIONS

2018 ◽  
Vol 10 (1) ◽  
pp. 147
Author(s):  
Sudha Bai R. ◽  
Remakanthan A. ◽  
Hareesh Kumar H. ◽  
Aryakrishna U. K.
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Radical Scavenging ◽  
Free Radical Scavenging ◽  
Ms Medium ◽  
Methanolic Extracts ◽  
Grown Plant ◽  
Antibacterial Potential

Objective: To compare the phytochemicals, antioxidative capacity and antibacterial profile of methanolic extracts of callus and naturally propagated plant species-Trichosanthes cucumerina (L.) var. cucumerina and to optimize an ideal protocol for in vitro callus and shoot induction.Methods: The sterilized seeds of Trichosanthes cucumerina (L.) var. cucumerina were inoculated in half Murashige and Skoog (MS) basal medium devoid of growth hormones to raise aseptic seedlings. Explants from aseptic seedlings used for callus induction in MS medium fortified with varying combinations of N6–Benzyl amino purine (BAP), 1-Naphthalene acetic acid (NAA) and 2,4–Dichlorophenoxy acetic acid (2,4-D). For in vitro soot induction, MS medium supplemented with different concentrations of 2,4-D, BAP and Kinetin-either alone or in combinations were employed. The callus harvested on 21st and 45th days were analyzed for a comparison of the influence of age of callus on the quantity of secondary metabolites. For a comparison with the naturally grown plant, all experiments were carried out with extracts from callus and wild plants. The antioxidant capacity of methanolic extracts was evaluated by 2,2-Diphenyl-1 Picryl Hydrazyl (DPPH) free radical scavenging assay and Ferric Reducing Antioxidant Power (FRAP) analysis. The antibacterial activity of were screened by the agar diffusion method using pathogenic bacteria such as Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus and documented through measurement of the diameter of growth inhibition zone (IZ). Results: The results on in vitro culture indicated that MS medium with BAP (0.5 mg/l) and 2,4-D (1 mg/l) was ideal for callus induction. For shoot induction, supplementation of MS medium with BAP-0.5 mg/l, 2,4,D-1.0 mg/l and Kinetin-0.5 mg/l was found to be most favourable. Direct root induction from the callus was found to occur in medium fortified with BAP-0.5 mg/l, 2,4, D-0.5 mg/l and NAA-1.0 mg/l. The phytoconstituents quantified were alkaloids, flavonoids, tannins, phenols and terpenoids and their levels were higher in wild plant in comparison to callus. Naturally grown plant possesses higher free radical scavenging ability and ferric reducing power than callus. Results of antibacterial activity indicated that the Gram-positive strain (Staphylococcus aureus) was more sensitive than the Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa). The highest antibacterial activity recorded for naturally propagated plant extract against S. aureus (IZ = 13 mm) and was quite comparable with standard antibiotic cephatoxim (IZ = 20 mm) at 100mg concentration.Conclusion: Results concluded that this overexploited medicinal plant with lesser seed longevity could be successfully propagated by in vitro methods. The phytoconstituents with antioxidative and antibacterial potential were more abundant in naturally propagated plants than undifferentiated callus tissue. The extracts are potent antibacterial agents.

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