2,5-Dihydrophenylalanine as an inhibitor of microbial growth

1970 ◽  
Vol 16 (6) ◽  
pp. 545-547 ◽  
Author(s):  
Dorothy S. Genghof
Keyword(s):  
Synergistic Effect ◽  
Growth Inhibition ◽  
Filamentous Fungi ◽  
Molecular Basis ◽  
Microbial Growth ◽  
Relative Effectiveness ◽  
E Coli ◽  
Growth Of A Variety ◽  
Derivatives Of

DL-2,5-Dihydrophenylalanine (DHPA) inhibited the growth of a variety of bacteria representing 10 different genera. Three yeasts were also sensitive to DHPA but only two of nine filamentous fungi were inhibited. The relative effectiveness of DHPA isomers as growth antagonists for S. cerevisiae and E. coli has also been investigated, and, on a molecular basis, DL-DHPA was found to be half as effective as L-DHPA against both of these microorganisms. This DHPA inhibition was reversed by addition of equimolar amounts of phenylalanine. Acetyl derivatives of L-DHPA and DL-DHPA were only slightly inhibitory for S. cerevisiae. A synergistic effect on the DHPA-induced growth inhibition of S. cerevisiae was observed when tyrosine was added to the medium.

Structure-Activity Relationship and Antimicrobial Evaluation of N-Phenylpyrazole Curcumin Derivatives

2020 ◽  
Vol 16 (4) ◽  
pp. 481-488
Author(s):  
Heli Sanghvi ◽  
Satyendra Mishra
Keyword(s):  
Antibacterial Activity ◽  
Gram Negative Bacteria ◽  
Pyrazole Derivatives ◽  
Gram Positive ◽  
Gram Negative ◽  
E Coli ◽  
Curcumin Derivatives ◽  
Structure Activity ◽  
Electron Donating Groups ◽  
Derivatives Of

Background: Curcumin, one of the most important pharmacologically significant natural products, has gained significant consideration among scientists for decades since its multipharmacological activities. 1, 3-Dicarbonyl moiety of curcumin was found to be accountable for the rapid degradation of curcumin molecule. The aim of present work is to replace 1, 3-dicarbonyl moiety of curcumin by pyrazole and phenylpyrazole derivatives with a view to improving its stability and to investigate the role of substitution in N-phenylpyrazole curcumin on its antibacterial activity against both Gram-positive as well as Gram-negative bacteria. Methods: Pyrazole derivatives of curcumin were prepared by heating curcumin with phenyhydrazine/ substituted phenyhydrazine derivatives in AcOH. The residue was purified by silica gel column chromatography. Structures of purified compounds were confirmed by 1H NMR and Mass spectroscopy. The synthesized compounds were evaluated for their antibacterial activity by the microdilution broth susceptibility test method against gram positive (S. aureus) and gram negative (E. coli). Results: Effects of substitution in N-phenylpyrazole curcumin derivatives against S. aureus and E. coli were studied. The most active N-(3-Nitrophenylpyrazole) curcumin (12) exhibits twenty-fold more potency against S. aureus (MIC: 10μg/mL)) and N-(2-Fluoroophenylpyrazole) curcumin (5) fivefold more potency against E. coli (MIC; 50 μg/mL) than N-phenylpyrazole curcumin (4). Whereas, a remarkable decline in anti-bacterial activity against S. aureus and E. coli was observed when electron donating groups were incorporated in N-phenylpyrazole curcumin (4). Comparative studies of synthesized compounds suggest the effects of electron withdrawing and electron donating groups on unsubstituted phenylpyrazole curcumin (4). Conclusion: The structure-activity relationship (SAR) results indicated that the electron withdrawing and electron donating at N-phenylpyrazole curcumin played key roles for their bacterial inhibitory effects. The results of the antibacterial evaluation showed that the synthesized pyrazole derivatives of curcumin displayed moderate to very high activity in S. aureus. In conclusion, the series of novel curcumin derivatives were designed, synthesized and tested for their antibacterial activities against S. aureus and E. coli. Among them, N-(3-Nitrophenylpyrazole curcumin; 12) was most active against S. aureus (Gram-positive) and N-(2-Fluoroophenylpyrazole) curcumin (5) against E. coli (Gram-negative) bacteria.

scholarly journals A genetically detoxified derivative of heat-labile Escherichia coli enterotoxin induces neutralizing antibodies against the A subunit.

1994 ◽  
Vol 180 (6) ◽  
pp. 2147-2153 ◽  
Author(s):  
M Pizza ◽  
M R Fontana ◽  
M M Giuliani ◽  
M Domenighini ◽  
C Magagnoli ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Cholera Toxin ◽  
Neutralizing Antibodies ◽  
Site Directed Mutagenesis ◽  
Directed Mutagenesis ◽  
E Coli ◽  
Heat Labile ◽  
A Subunit ◽  
Adp Ribosyltransferase ◽  
Derivatives Of

Escherichia coli enterotoxin (LT) and the homologous cholera toxin (CT) are A-B toxins that cause travelers' diarrhea and cholera, respectively. So far, experimental live and killed vaccines against these diseases have been developed using only the nontoxic B portion of these toxins. The enzymatically active A subunit has not been used because it is responsible for the toxicity and it is reported to induce a negligible titer of toxin neutralizing antibodies. We used site-directed mutagenesis to inactivate the ADP-ribosyltransferase activity of the A subunit and obtained nontoxic derivatives of LT that elicited a good titer of neutralizing antibodies recognizing the A subunit. These LT mutants and equivalent mutants of CT may be used to improve live and killed vaccines against cholera and enterotoxinogenic E. coli.

Microbial Growth Response to Hydrogel Encapsulated Quantum Dot Nanospheres

2007 ◽  
Vol 1064 ◽  
Author(s):  
Somesree GhoshMitra ◽  
Tong Cai ◽  
Santaneel Ghosh ◽  
Arup Neogi ◽  
Zhibing Hu ◽  
...  
Keyword(s):  
Electron Microscopy ◽  
Growth Response ◽  
Microbial Growth ◽  
Biological Effects ◽  
Growth Curves ◽  
Swelling Properties ◽  
Growth Environment ◽  
E Coli ◽  
Cdte Qds ◽  
Biological Compatibility

ABSTRACTQuantum dots (QDs) are now used extensively for labeling in biomedical research due to their unique photoluminescence behavior, involving size-tunable emission color, a narrow and symmetric emission profile and a broad excitation range [1]. Uncoated QDs made of CdTe core are toxic to cells because of release of Cd2+ ions into the cellular environment. This problem can be partially solved by encapsulating QDs with polymers, like poly(N-isopropylacrylamide) (PNIPAM) or poly(ethylene glycol) (PEG). Based on biological compatibility, fast response as well as pH, temperature and magnetic field dependent swelling properties, hydrogel nanospheres has become carriers of drugs, fluorescence labels, magnetic particles for hyperthermia applications and particles that have strong optical absorption profiles for optical excitation. The toxicity of uncoated QDs are known; however, there have been a very limited number of studies specially designed to assess thoroughly the toxicity of nanosphere encapsulated QDs against QD density and dosing level.In this work, we present preliminary studies of biological effects of a novel QD based nanomaterial system on Escherichia coli (E. coli) bacteria. Cadmium chalcogenide QDs provide the most attractive fluorescence labels in comparison with routine dyes or metal complexes. Nanospheres on the other hand are the most commonly used carriers of fluorescence labels for fluorescence detection. The integration of fluorescent QDs in nanospheres therefore provides a new generation of fluorescence markers for biological assays. Hydrogels based on PNIPAM is a well known thermoresponsive polymer that undergoes a volume phase transition across the low critical solution (LCST) [2]. Therefore, the inherent temperature-sensitive swelling properties of PNIPAM offer the potentiality to control QD density within the nanospheres. In the present work, E. coli growth was monitored as E. coli served as a representation of how cells might respond in the presence of hydrogel encapsulated QDs in their growth environment. The present work describes the successful encapsulation of CdTe QDs in PNIPAM gel network. Microgel encapsulated QDs were synthesized by first preparing PNIPAM microspheres with cystaminebisacrylamide as a crosslinker and CdTe QDs capped with a stabilizer. The CdTe QDs were bonded into PNIPAM microgels through the replacement of CdTe's stabilizer inside PNIPAM microspheres. Growth curves were generated for E. coli growing in 20 mL of LB media containing hydrogel encapsulated QD nanospheres (400 nm diameter) at relatively higher (0.5mg/mL) and lower (0.01mg/mL) concentration of solution. From the growth curves, there was no evidence at lower concentration (0.01mg/mL) that the hydrogel encapsulated QDs prevent the microbial cells from growing but at higher concentration (0.5mg/mL), microbial growth was inhibited. Transmission Electron Microscopy (TEM) was used to characterize QD size and density inside the hydrogel nanospheres. Scanning Electron Microscopy (SEM) was used to observe size and morphology of the hydrogel particles. Further investigation is going on cell growth response at different QD density and to evaluate the limiting hydrogel concentration for different QD densities.

Effects of pteridines on chloramine-T-induced growth inhibition in E. coli strains: Correlations with molecular structure

1996 ◽  
Vol 21 (2) ◽  
pp. 133-138 ◽  
Author(s):  
Renate Horejsi ◽  
Willibald Estelberger ◽  
Walter Mlekusch ◽  
Reinhard Möller ◽  
Karl Öttl ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Growth Inhibition ◽  
E Coli ◽  
Chloramine T

scholarly journals Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

2016 ◽  
Vol 12 ◽  
pp. 2588-2601 ◽  
Author(s):  
Vladimir A Stepchenko ◽  
Anatoly I Miroshnikov ◽  
Frank Seela ◽  
Igor A Mikhailopulo
Keyword(s):  
Purine Nucleoside Phosphorylase ◽  
Reaction Conditions ◽  
E Coli ◽  
No Formation ◽  
Structural Peculiarities ◽  
Substrate Properties ◽  
Nucleoside Phosphorylases ◽  
Derivatives Of

The trans-2-deoxyribosylation of 4-thiouracil (4SUra) and 2-thiouracil (2SUra), as well as 6-azauracil, 6-azathymine and 6-aza-2-thiothymine was studied using dG and E. coli purine nucleoside phosphorylase (PNP) for the in situ generation of 2-deoxy-α-D-ribofuranose-1-phosphate (dRib-1P) followed by its coupling with the bases catalyzed by either E. coli thymidine (TP) or uridine (UP) phosphorylases. 4SUra revealed satisfactory substrate activity for UP and, unexpectedly, complete inertness for TP; no formation of 2’-deoxy-2-thiouridine (2SUd) was observed under analogous reaction conditions in the presence of UP and TP. On the contrary, 2SU, 2SUd, 4STd and 2STd are good substrates for both UP and TP; moreover, 2SU, 4STd and 2’-deoxy-5-azacytidine (Decitabine) are substrates for PNP and the phosphorolysis of the latter is reversible. Condensation of 2SUra and 5-azacytosine with dRib-1P (Ba salt) catalyzed by the accordant UP and PNP in Tris∙HCl buffer gave 2SUd and 2’-deoxy-5-azacytidine in 27% and 15% yields, respectively. 6-Azauracil and 6-azathymine showed good substrate properties for both TP and UP, whereas only TP recognizes 2-thio-6-azathymine as a substrate. 5-Phenyl and 5-tert-butyl derivatives of 6-azauracil and its 2-thioxo derivative were tested as substrates for UP and TP, and only 5-phenyl- and 5-tert-butyl-6-azauracils displayed very low substrate activity. The role of structural peculiarities and electronic properties in the substrate recognition by E. coli nucleoside phosphorylases is discussed.

Craniofacial, vestibular and bone defects in mice lacking the Distal-less-related gene Dlx5

Development ◽  
1999 ◽  
Vol 126 (17) ◽  
pp. 3795-3809 ◽  
Author(s):  
D. Acampora ◽  
G.R. Merlo ◽  
L. Paleari ◽  
B. Zerega ◽  
M.P. Postiglione ◽  
...  
Keyword(s):  
Developmental Stages ◽  
Brain Regions ◽  
Lacz Gene ◽  
Vestibular Organ ◽  
E Coli ◽  
Branchial Arches ◽  
Homeobox Protein ◽  
Derivatives Of ◽  
Delayed Ossification ◽  
Newborn Animals

The Dlx5 gene encodes a Distal-less-related DNA-binding homeobox protein first expressed during early embryonic development in anterior regions of the mouse embryo. In later developmental stages, it appears in the branchial arches, the otic and olfactory placodes and their derivatives, in restricted brain regions, in all extending appendages and in all developing bones. We have created a null allele of the mouse Dlx5 gene by replacing exons I and II with the E. coli lacZ gene. Heterozygous mice appear normal. Beta-galactosidase activity in Dlx5+/− embryos and newborn animals reproduces the known pattern of expression of the gene. Homozygous mutants die shortly after birth with a swollen abdomen. They present a complex phenotype characterised by craniofacial abnormalities affecting derivatives of the first four branchial arches, severe malformations of the vestibular organ, a delayed ossification of the roof of the skull and abnormal osteogenesis. No obvious defect was observed in the patterning of limbs and other appendages. The defects observed in Dlx5−/− mutant animals suggest multiple and independent roles of this gene in the patterning of the branchial arches, in the morphogenesis of the vestibular organ and in osteoblast differentiation.

scholarly journals Comparison of Single and Combined Use of Catechin, Protocatechuic, and Vanillic Acids as Antioxidant and Antibacterial Agents against Uropathogenic Escherichia Coli at Planktonic and Biofilm Levels

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2813 ◽  
Author(s):  
Ariadna Bernal-Mercado ◽  
Francisco Vazquez-Armenta ◽  
Melvin Tapia-Rodriguez ◽  
Maria Islas-Osuna ◽  
Veronica Mata-Haro ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Phenolic Compounds ◽  
Synergistic Effect ◽  
Vanillic Acid ◽  
Protocatechuic Acid ◽  
Uropathogenic Escherichia Coli ◽  
E Coli ◽  
Planktonic Bacteria ◽  
Combined Use ◽  
Antioxidant Agents

The objective of this study was to evaluate the effect of combining catechin, protocatechuic, and vanillic acids against planktonic growing, adhesion, and biofilm eradication of uropathogenic Escherichia coli (UPEC), as well as antioxidant agents. The minimum inhibitory concentrations (MIC) of protocatechuic, vanillic acids and catechin against the growth of planktonic bacteria were 12.98, 11.80, and 13.78 mM, respectively. Mixing 1.62 mM protocatechuic acid + 0.74 mM vanillic acid + 0.05 mM catechin resulted in a synergistic effect acting as an MIC. Similarly, the minimum concentrations of phenolic compounds to prevent UPEC adhesion and biofilm formation (MBIC) were 11.03 and 7.13 mM of protocatechuic and vanillic acids, respectively, whereas no MBIC of catechin was found. However, combinations of 1.62 mM protocatechuic acid + 0.74 mM vanillic acid + 0.05 mM catechin showed a synergistic effect acting as MBIC. On the other hand, the minimum concentrations to eradicate biofilms (MBEC) were 25.95 and 23.78 mM, respectively. The combination of 3.20 mM protocatechuic acid, 2.97 mM vanillic acid, and 1.72 mM catechin eradicated pre-formed biofilms. The antioxidant capacity of the combination of phenolics was higher than the expected theoretical values, indicating synergism by the DPPH•, ABTS, and FRAP assays. Effective concentrations of catechin, protocatechuic, and vanillic acids were reduced from 8 to 1378 times when combined. In contrast, the antibiotic nitrofurantoin was not effective in eradicating biofilms from silicone surfaces. In conclusion, the mixture of phenolic compounds was more effective in preventing cell adhesion and eradicating pre-formed biofilms of uropathogenic E. coli than single compounds and nitrofurantoin, and showed antioxidant synergy.

scholarly journals Alkaloid-Rich Crude Extracts, Fractions and Piperamide Alkaloids of Piper guineense Possess Promising Antibacterial Effects

Antibiotics ◽  
2018 ◽  
Vol 7 (4) ◽  
pp. 98 ◽  
Author(s):  
Eunice Mgbeahuruike ◽  
Pia Fyhrquist ◽  
Heikki Vuorela ◽  
Riitta Julkunen-Tiitto ◽  
Yvonne Holm
Keyword(s):  
Antibacterial Activity ◽  
Pathogenic Bacteria ◽  
Bacterial Resistance ◽  
Hot Water ◽  
Bacterial Strains ◽  
Inhibitory Effects ◽  
Piper Guineense ◽  
E Coli ◽  
Growth Inhibitory ◽  
Derivatives Of

Piper guineense is a food and medicinal plant commonly used to treat infectious diseases in West-African traditional medicine. In a bid to identify new antibacterial compounds due to bacterial resistance to antibiotics, twelve extracts of P. guineense fruits and leaves, obtained by sequential extraction, as well as the piperine and piperlongumine commercial compounds were evaluated for antibacterial activity against human pathogenic bacteria. HPLC-DAD and UHPLC/Q-TOF MS analysis were conducted to characterize and identify the compounds present in the extracts with promising antibacterial activity. The extracts, with the exception of the hot water decoctions and macerations, contained piperamide alkaloids as their main constituents. Piperine, dihydropiperine, piperylin, dihydropiperylin or piperlonguminine, dihydropiperlonguminine, wisanine, dihydrowisanine and derivatives of piperine and piperidine were identified in a hexane extract of the leaf. In addition, some new piperamide alkaloids were identified, such as a piperine and a piperidine alkaloid derivative and two unknown piperamide alkaloids. To the best of our knowledge, there are no piperamides reported in the literature with similar UVλ absorption maxima and masses. A piperamide alkaloid-rich hexane leaf extract recorded the lowest MIC of 19 µg/mL against Sarcina sp. and gave promising growth inhibitory effects against S. aureus and E. aerogenes as well, inhibiting the growth of both bacteria with a MIC of 78 µg/mL. Moreover, this is the first report of the antibacterial activity of P. guineense extracts against Sarcina sp. and E. aerogenes. Marked growth inhibition was also obtained for chloroform extracts of the leaves and fruits against P. aeruginosa with a MIC value of 78 µg/mL. Piperine and piperlongumine were active against E. aerogenes, S. aureus, E. coli, S. enterica, P. mirabilis and B. cereus with MIC values ranging from 39–1250 µg/mL. Notably, the water extracts, which were almost devoid of piperamide alkaloids, were not active against the bacterial strains. Our results demonstrate that P. guineense contains antibacterial alkaloids that could be relevant for the discovery of new natural antibiotics.

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