Synthesis, DNA affinity, and antimicrobial activity of 4-substituted phenyl-2,2′-bichalcophenes and aza-analogues

Youssef, Magdy M.; Al‐Omair, Mohammed A.; Ismail, Mohamed A.

doi:10.1007/s00044-011-9964-y

Cited by 30 publications

(34 citation statements)

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“…However, these exhibit a number of serious side effects, toxicity problems, and poor availability 4. Recently, a series of pentamidine-related 4-substituted phenyl bichalcophenes and aza-analogs (Figure 1) were synthesized,5 and shown to exhibit structurally related broad-spectrum antimicrobial activities against Gram positive and Gram negative bacteria 6. In addition, these novel bichalcophenes were not toxic to the mouse hepa1c1c7 cells up to 200 μM and the IC 50 values were >450 μM suggesting their possible clinical use.…”

Section: Introductionmentioning

confidence: 99%

Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2'-bichalcophenes and aza-analogs

El‐Sayed¹,

Hussin²

2013

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Evaluation of the potential antimutagenic activities of new compounds by Ames assay has been of great interest for the development of novel therapeutics for many diseases including cancer. Ten novel bichalcophenes with in vitro and in vivo broad spectrum activities against various microbial strains were investigated throughout the present study for their cytotoxic, antioxidant, and antimutagenic potential in a Salmonella reverse mutation assay system against sodium azide (NaN3) and benzo[a]pyrene (B[a]P). At nontoxic concentrations, all bichalcophenes alone or in combination with NaN3 (1 μg/plate) or B[a]P (20 μM) with S9 mix were not mutagenic. The bichalcophenes significantly reduced NaN3- and B[a]P-induced mutagenicity under pre-exposure and co-exposure conditions in a concentration-independent manner. However, the antimutagenic activity of bichalcophenes against B[a]P varied depending on the exposure regimen, being more effective under pre-exposure conditions. The antimutagenic activity was correlated with a high antioxidant activity that could promote the DNA repair system. Bichalcophenes are least likely to interfere with the microsomal bioactivation of B[a]P. Monocationic bichalcophenes were superior to the corresponding mononitriles as antimutagenic agents against both mutagens investigated, possibly due to the higher nucleophilic centers they have which could bind and protect the bacterial DNA. Three monocationic compounds were shown to have a strong anticancer activity against the 58 cell line. Based on the results of the present investigation, monocationic compounds (1, 4, and 5B) will be selected for further time consuming and costly chemoprevention studies in animal models.

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Section: Introductionmentioning

confidence: 99%

Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2'-bichalcophenes and aza-analogs

El‐Sayed¹,

Hussin²

2013

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“…Different mechanisms for DNA cleavage have been assumed, including hydrolytic effects or oxidative pathways. Hydrolytic cleavage directly breaks down the phosphodiester bond but does not result in sugar damage (Youssef et al, 2012;Ibrahim et al, 2011). The phosphodiester backbone of DNA is stable and resists hydrolytic cleavage.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Biological Evaluation of Novel Thiadiazoline Sulfonamides and Metal Complexes

Sayed¹,

Youssef²,

Faiyz³

2015

J. of Applied Sciences

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A B S T R A C TIn the present work, we reported a novel thiadiazoline sulfonamide derivatives and their metal complexes were efficiently synthesized based on N-phenyl 2-pyridine carbohydrazonoyl halide. Synthesized compounds were elucidated by elemental analysis and spectral data. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against Gram negative (Escherichia coli and Pseudomonas aeruginosa), Gram positive (Staphylococcus aureus and Bacillus subtilis) bacterial strains and fungal strain Saccharomyces cerevisiae. The minimum inhibitory concentration of the synthesized compounds against various microorganisms was also determined. The synthesized thiadiazoline sulfonamide derivatives and metal complexes had superoxide dismutase-like activity and inhibited superoxide radical generation. Moreover, these organic compounds induced a wide range of DNA and protein degradation processes, based on agarose gel and sodium dodecyl sulfate-polyacrylamide gel electrophoresis analyses, respectively.

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“…Thus, 1 H NMR spectrum of compound 5a displayed singlet signal at δ 9.44 (4H) characteristic for the cationic amidine group in addition to the signals corresponding to the trisubstituted benzene ring and bifuran moiety. Fluoroarylbichalcophene mononitriles 4a–e were prepared adopting a Stille coupling reaction between the corresponding bromo compounds 3a–c and 2-(tri- n -butylstannyl)furan or analogues using our previously described methodology for the preparation of non-fluorinated bichalcophene analogues 18. The structures of compounds 4a–e were assigned based on their spectral and elemental analyses.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of the biological activity of novel monocationic fluoroaryl-2,2’-bichalcophenes and their analogues

Hussin

Ismail

Abdullah

et al. 2014

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A series of bichalcophene fluorobenzamidines 5a–e was synthesized from the corresponding mononitriles 4a–e via a direct reaction with lithium bis(trimethylsilyl)amide LiN(TMS)2 followed by de-protection with ethanolic HCl (gas). Bichalcophene fluorobenzonitriles 4a–e were prepared adopting a Stille coupling reaction between the bromo compounds 3a–c and 2-(tri-n-butylstannyl)furan or analogues. As an approach to drug discovery, the structure–antimutagenicity relationship of novel fluoroarylbichalcophenes was examined using the Ames Salmonella/microsomal assay. At nontoxic concentrations (10 and 20 μM), all derivatives alone or in combination with sodium azide (NaN3; 2 μg/plate) or benzo[a]pyrene (B[a]P; 20 μM) in the presence of S9 mix were not mutagenic. The fluoroaryl derivatives significantly reduced the NaN3-induced and B[a]P-induced mutagenicity under pre-exposure and co-exposure conditions. The recorded antimutagenic activity of fluoroaryl derivatives varied depending on the kind of mutagen and the exposure regimen. Monocationic fluoroarylbichalcophenes were superior to the corresponding mononitriles in reducing B[a]P-induced mutagenicity. Nevertheless, mononitriles were more active against NaN3, especially at low concentrations and under pre-exposure treatments. The antimutagenic activity was congruent with a high antioxidant activity that could promote the DNA repair system. The fluorine substitution changed the antimutagenic signature of bichalcophenes. Some of these compounds could be selected for further anticancer studies.

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Synthesis, DNA affinity, and antimicrobial activity of 4-substituted phenyl-2,2′-bichalcophenes and aza-analogues

Cited by 30 publications

References 20 publications

Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2'-bichalcophenes and aza-analogs

Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2'-bichalcophenes and aza-analogs

Synthesis, Characterization and Biological Evaluation of Novel Thiadiazoline Sulfonamides and Metal Complexes

Evaluation of the biological activity of novel monocationic fluoroaryl-2,2’-bichalcophenes and their analogues

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Synthesis, DNA affinity, and antimicrobial activity of 4-substituted phenyl-2,2′-bichalcophenes and aza-analogues

Cited by 30 publications

References 20 publications

Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2&#39;-bichalcophenes and aza-analogs

Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2&#39;-bichalcophenes and aza-analogs

Synthesis, Characterization and Biological Evaluation of Novel Thiadiazoline Sulfonamides and Metal Complexes

Evaluation of the biological activity of novel monocationic fluoroaryl-2,2&rsquo;-bichalcophenes and their analogues

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Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2'-bichalcophenes and aza-analogs

Antimutagenic and antioxidant activity of novel 4-substituted phenyl-2,2'-bichalcophenes and aza-analogs

Evaluation of the biological activity of novel monocationic fluoroaryl-2,2’-bichalcophenes and their analogues