In vitro cytotoxicity and antimicrobial activity of Talaromyces flavus SP5 inhabited in the marine sediment of Southern Coast of India

In a drug-repurposing-driven approach for speeding up the development of novel antimicrobial agents, this paper presents for the first time in the scientific literature the synthesis, physico-chemical characterization, in silico analysis, antimicrobial activity against bacterial and fungal strains in planktonic and biofilm growth state, as well as the in vitro cytotoxicity of some new 6,11-dihydrodibenz[b,e]oxepin-11(6H)one O-(arylcarbamoyl)oximes. The structures of intermediary and final substances (compounds 7a–j) were confirmed by 1H-NMR, 13C-NMR and IR spectra, as well as by elemental analysis. The in silico bioinformatic and cheminformatic studies evidenced an optimal pharmacokinetic profile for the synthesized compounds 7a–j, characterized by an average lipophilic character predicting good cell membrane permeability and intestinal absorption; low maximum tolerated dose for humans; potassium channels encoded by the hERG I and II genes as potential targets and no carcinogenic effects. The obtained compounds exhibited a higher antimicrobial activity against the planktonic Gram-positive Staphylococcus aureus and Bacillus subtilis strains and the Candida albicans fungal strain. The obtained compounds also inhibited the ability of S. aureus, B. subtilis, Escherichia coli and C. albicans strains to colonize the inert substratum, accounting for their possible use as antibiofilm agents. All the active compounds exhibited low or acceptable cytotoxicity levels on the HCT8 cells, ensuring the potential use of these compounds for the development of new antimicrobial drugs with minimal side effects on the human cells and tissues.

Download Full-text

Design, Synthesis and In Vitro Characterization of Novel Antimicrobial Agents Based on 6-Chloro-9H-carbazol Derivatives and 1,3,4-Oxadiazole Scaffolds

Molecules ◽

10.3390/molecules25020266 ◽

2020 ◽

Vol 25 (2) ◽

pp. 266 ◽

Cited By ~ 5

Author(s):

Alexandra T. Bordei Telehoiu ◽

Diana C. Nuță ◽

Miron T. Căproiu ◽

Florea Dumitrascu ◽

Irina Zarafu ◽

...

Keyword(s):

Antimicrobial Activity ◽

Antimicrobial Agents ◽

Oral Absorption ◽

Phosphorus Oxychloride ◽

In Vitro Cytotoxicity ◽

Mutagenic Potential ◽

Design Synthesis ◽

Acyl Chlorides ◽

Hydrazide Derivative

In this paper, we aimed to exploit and combine in the same molecule the carbazole and the 1,3,4-oxadiazole pharmacophores, to obtain novel carprofen derivatives, by using two synthesis pathways. For the first route, the following steps have been followed: (i) (RS)-2-(6-chloro-9H-carbazol-2-yl)propanonic acid (carprofen) treatment with methanol, yielding methyl (RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate; (ii) the resulted methylic ester was converted to (RS)-2-(6-chloro-9H-carbazol-2-yl)propane hydrazide (carprofen hydrazide) by treatment with hydrazine hydrate; (iii) reaction of the hydrazide derivative with acyl chlorides led to N-[(2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoil]-N′-R-substituted-benzoylhydrazine formation, which; (iv) in reaction with phosphorus oxychloride gave the (RS)-1-(6-chloro-9H-carbazol-2-yl)-1-(1,3,4-oxadiazol-2-yl)ethane derivatives. In the second synthesis pathway, new 1,3,4-oxadiazole ring compounds were obtained starting from carprofen which was reacted with isoniazid, in the presence of phosphorus oxychloride to form (RS)-1-(6-chloro-9H-carbazol-2-yl)-1-[5-(4-pyridyl)-1,3,4-oxadiazol-2-yl]ethane. The synthesized compounds were characterized by IR, 1H-NMR and 13C-NMR, screened for their drug-like properties and evaluated for in vitro cytotoxicity and antimicrobial activity. The obtained compounds exhibited a good antimicrobial activity, some of the compounds being particularly active on E. coli, while others on C. albicans. The most significant result is represented by their exceptional anti-biofilm activity, particularly against the P. aeruginosa biofilm. The cytotoxicity assay revealed that at concentrations lower than 100 μg/mL, the tested compounds do not induce cytotoxicity and do not alter the mammalian cell cycle. The new synthesized compounds show good drug-like properties. The ADME-Tox profiles indicate a good oral absorption and average permeability through the blood brain barrier. However, further research is needed to reduce the predicted mutagenic potential and the hepatotoxicity.

Download Full-text

Derivatives of 3-Aminopyrazine-2-carboxamides: Synthesis, Antimicrobial Evaluation, and in Vitro Cytotoxicity

Molecules ◽

10.3390/molecules24071212 ◽

2019 ◽

Vol 24 (7) ◽

pp. 1212 ◽

Cited By ~ 4

Author(s):

Ghada Bouz ◽

Lucia Semelková ◽

Ondřej Janďourek ◽

Klára Konečná ◽

Pavla Paterová ◽

...

Keyword(s):

Antimicrobial Activity ◽

Antibacterial Activity ◽

Three Dimensional ◽

Cancer Cell Line ◽

Antimycobacterial Activity ◽

In Vitro Cytotoxicity ◽

Antibacterial And Antifungal Activities ◽

Alkyl Derivatives ◽

Current Series

We report the design, synthesis, and in vitro antimicrobial activity of a series of N-substituted 3-aminopyrazine-2-carboxamides with free amino groups in position 3 on the pyrazine ring. Based on various substituents on the carboxamidic moiety, the series is subdivided into benzyl, alkyl, and phenyl derivatives. The three-dimensional structures of the title compounds were predicted using energy minimization and low mode molecular dynamics under AMBER10:EHT forcefield. Compounds were evaluated for antimycobacterial, antibacterial, and antifungal activities in vitro. The most active compound against Mycobacterium tuberculosis H37Rv (Mtb) was 3-amino-N-(2,4-dimethoxyphenyl)pyrazine-2-carboxamide (17, MIC = 12.5 µg/mL, 46 µM). Antimycobacterial activity against Mtb and M. kansasii along with antibacterial activity increased among the alkyl derivatives with increasing the length of carbon side chain. Antibacterial activity was observed for phenyl and alkyl derivatives, but not for benzyl derivatives. Antifungal activity was observed in all structural subtypes, mainly against Trichophyton interdigitale and Candida albicans. The four most active compounds (compounds 10, 16, 17, 20) were evaluated for their in vitro cytotoxicity in HepG2 cancer cell line; only compound 20 was found to exert some level of cytotoxicity. Compounds belonging to the current series were compared to previously published, structurally related compounds in terms of antimicrobial activity to draw structure activity relationships conclusions.

Download Full-text

Chemical Composition and Bioactivity of the Leaf Oil of Calyptranthes pallens (Poir.) Griseb. from Abaco Island, Bahamas

Natural Product Communications ◽

10.1177/1934578x0600100407 ◽

2006 ◽

Vol 1 (4) ◽

pp. 1934578X0600100 ◽

Cited By ~ 1

Author(s):

Anita Bansal ◽

Amelia K. Boehme ◽

Lauren C. Eiter ◽

Jennifer M. Schmidt ◽

William N. Setzer ◽

...

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Antimicrobial Activity ◽

Human Tumor ◽

In Vitro Cytotoxicity ◽

Hep G2 ◽

Human Tumor Cells ◽

Leaf Oil ◽

Oil Components

The leaf oil of Calyptranthes pallens was obtained by hydrodistillation and analyzed by GC/MS. The most abundant oil components were the monoterpenoids α-pinene (24.7%), α-terpineol (13.8%), and trans-pinocarveol (11.6%). The antimicrobial activity against Bacillus cereus, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, and Aspergillus niger, and the in-vitro cytotoxicity of the oil on Hep G2, MDA-MB-231, Hs 578T, and PC-3 human tumor cells were also examined.

Download Full-text

Scientific validation of the antimicrobial and antiproliferative potential of Berberis aristata DC root bark, its phytoconstituents and their biosafety

AMB Express ◽

10.1186/s13568-019-0868-4 ◽

2019 ◽

Vol 9 (1) ◽

Cited By ~ 2

Author(s):

Henna Sood ◽

Yashwant Kumar ◽

Vipan Kumar Gupta ◽

Daljit Singh Arora

Keyword(s):

Antimicrobial Activity ◽

Ethyl Acetate ◽

Broad Spectrum ◽

In Vitro Cytotoxicity ◽

Behavioral Pattern ◽

Root Bark ◽

Potential Candidate ◽

Oral Toxicity ◽

Antibiotic Effect

Abstract Berberis aristata is an important part of traditional healing system from more than 2500 years. The aqueous extract of Berberis aristata root bark displayed broad spectrum activity against 13 test pathogens, ranging from 12 to 25 mm. In classical optimization, 15% concentration prepared at 40 °C for 40 min was optimal and thermostable. Statistical optimization enhanced the activity by 1.13–1.30-folds. Ethyl acetate was the best organic solvent to elute out the potential compound responsible for antimicrobial activity. Diterpenes were the most abundant phytoconstituent (15.3%) and showed broad spectrum antimicrobial activity ranging from 16.66 to 42.66 mm. Ethyl acetate extract displayed the lowest minimum inhibitory concentration (0.05–1 mg/mL), followed by diterpenes (0.05–5 mg/mL) and flavonoids (0.05–10 mg/mL). The test extracts were microbicidal in nature and showed a prolonged post antibiotic effect ranging from 2 to 8 h. They were found to be biosafe as per Ames and MTT assay. The in vitro cytotoxicity evaluation of diterpenes against L20B, RD and Hep 2 cell lines revealed its IC50 ranging from 245 to 473 µg/mL. Acute oral toxicity of diterpenes on Swiss albino mice did not show any changes in behavioral pattern, body weight, biochemical parameters as well as organs’ architecture. The study thus indicates B. aristata could be a potential candidate for development of potent drug owing to its antimicrobial potential and biosafe profile.

Download Full-text

Parent and nano-encapsulated ytterbium(iii) complex toward binding with biological macromolecules, in vitro cytotoxicity, cleavage and antimicrobial activity studies

RSC Advances ◽

10.1039/d0ra03895d ◽

2020 ◽

Vol 10 (39) ◽

pp. 23002-23015 ◽

Cited By ~ 1

Author(s):

Zahra Aramesh-Boroujeni ◽

Shohreh Jahani ◽

Mozhgan Khorasani-Motlagh ◽

Kagan Kerman ◽

Meissam Noroozifar

Keyword(s):

Antimicrobial Activity ◽

Dna Cleavage ◽

In Vitro Cytotoxicity ◽

Biological Macromolecules ◽

Biological Applications

The biological applications of Yb-complexes including anticancer, antimicrobial and DNA cleavage ability, and their interaction with FS-DNA and BSA were examined.

Download Full-text