2,5-Dihydroxybenzaldehyde

Molecules. 2014 Jun 6;19(6):7497-515.

Effect of structure on the interactions between five natural antimicrobial compounds and phospholipids of bacterial cell membrane on model monolayers.[Pubmed: 24914896]

Monolayers composed of bacterial phospholipids were used as model membranes to study interactions of the naturally occurring phenolic compounds 2,5-Dihydroxybenzaldehyde and 2-hydroxy-5-methoxybenzaldehyde, and the plant essential oil compounds carvacrol, cinnamaldehyde, and geraniol, previously found to be active against both Gram-positive and Gram-negative pathogenic microorganisms.
METHODS AND RESULTS:
The lipid monolayers consist of 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine (DPPE), 1,2-dihexa- decanoyl-sn-glycero-3-phospho-(1'-rac-glycerol) (DPPG), and 1,1',2,2'-tetratetradecanoyl cardiolipin (cardiolipin). Surface pressure-area (π-A) and surface potential-area (Δψ-A) isotherms were measured to monitor changes in the thermodynamic and physical properties of the lipid monolayers. Results of the study indicated that the five compounds modified the three lipid monolayer structures by integrating into the monolayer, forming aggregates of antimicrobial -lipid complexes, reducing the packing effectiveness of the lipids, increasing the membrane fluidity, and altering the total dipole moment in the monolayer membrane model. The interactions of the five antimicrobial compounds with bacterial phospholipids depended on both the structure of the antimicrobials and the composition of the monolayers.
CONCLUSIONS:
The observed experimental results provide insight into the mechanism of the molecular interactions between naturally-occurring antimicrobial compounds and phospholipids of the bacterial cell membrane that govern activities.

Langmuir. 2012 Oct 2;28(39):14055-64.

Diffusion-free mediator based miniature biofuel cell anode fabricated on a carbon-MEMS electrode.[Pubmed: 22946444 ]

We report on the functionalization of a micropatterned carbon electrode fabricated using the carbon-MEMS process for its use as a miniature diffusion-free glucose oxidase anode.
METHODS AND RESULTS:
Carbon-MEMS based electrodes offer precise manufacturing control on both the micro- and nanoscale and possess higher electron conductivity than redox hydrogels. However, the process involves pyrolysis in a reducing environment that renders the electrode surface less reactive and introduction of a high density of functional groups becomes challenging. Our functionalization strategy involves the electrochemical oxidation of amine linkers onto the electrode. This strategy works well with both aliphatic and aryl linkers and uses stable compounds. The anode is designed to operate through mediated electron transfer between 2,5-Dihydroxybenzaldehyde (DHB) based redox mediator and glucose oxidase enzyme. The electrode was first functionalized with ethylene diamine (EDA) to serve as a linker for the redox mediator. The redox mediator was then grafted through reductive amination, and attachment was confirmed through cyclic voltammetry. The enzyme immobilization was carried out through either adsorption or attachment, and their efficiency was compared. For enzyme attachment, the DHB attached electrode was functionalized again through electro-oxidation of aminobenzoic acid (ABA) linker. The ABA functionalization resulted in reduction of the DHB redox current, perhaps due to increased steric hindrance on the electrode surface, but the mediator function was preserved. Enzyme attachment was then carried out through a coupling reaction between the free carboxyl group on the ABA linker and the amine side chains on the enzyme. The enzyme incubation for both adsorption and attachment was done either through a dry spotting method or wet spotting method. The dry spotting method calls for the evaporation of enzyme droplet to form a thin film before sealing the electrode environment, to increase the effective concentration of the enzyme on the electrode surface during incubation. The electrodes were finally protected with a gelatin based hydrogel film. The anode half-cell was tested using cyclic voltammetry in deoxygenated phosphate buffer saline solution pH 7.4 to minimize oxygen interference and to simulate the pH environment of the body. The electrodes that yielded the highest anodic current were prepared by enzyme attachment method with dry spotting incubation.
CONCLUSIONS:
A polarization response was generated for this anodic half-cell and exhibits operation close to maximum efficiency that is limited by the mass transport of glucose to the electrode.

Int J Biol Macromol. 2012 Dec;51(5):1159-66.

Synthesis and characterization of novel nano-chitosan Schiff base and use of lead (II) sensor.[Pubmed: 22982811]

A new kind of nano-chitosan Schiff base ligand (CHNS) with particle size of 34 nm was formed by the reaction between the 2-amino groups of glucosamine residue of nano-chitosan and a 2,5-Dihydroxybenzaldehyde.
METHODS AND RESULTS:
The chemical structures of the nano-chitosan and nano-chitosan Schiff base were characterized by FT-IR spectra, particle sizer, zeta potential, and elemental analysis. A new, simple and effective chemically modified carbon paste electrode with CHNS was prepared and used as a lead (II) sensor. The prepared electrode was characterized using scanning electronic microscopy (SEM-EDX) and cyclic voltammetry (CV). The modified electrode showed only one oxidation peak in the anodic scan at -0.34 V (vs. Ag/AgCl) for the oxidation of lead (II). The dedection limit (LOD) was calculated as 1.36×10(-7) for a 10-min preconcentration time at pH 6.0.

Comptes Rendus Chimie, 2016,20(4): 365-9.

Spectroscopic determination of the dissociation constants of 2,4- and 2,5-dihydroxybenzaldehydes and relationships to their antioxidant activities[Reference: WebLink]

METHODS AND RESULTS:
UV–visible spectra of 2,4-dihydroxybenzaldehyde and 2,5-Dihydroxybenzaldehyde (2,4DHB and 2,5DHB) are recorded in a wide range of pH. The dissociation pK values obtained from these measurements were 6.94 ± 0.03 and 9.28 ± 0.03 for 2,4DHB and 8.42 ± 0.03 and 10.93 ± 0.03 for 2,5DHB.
CONCLUSIONS:
The results indicate that the pH at which the assays for antioxidant capacity measurements are made is very important in light of the hydroxyl group dissociation, because of the different dissociation constants of the different isomers. The percentage of dissociation of each group is essential, the positions of these groups in the ring appearing as a secondary factor.