Chemical structure of polyoxyethylene (9) nonylphenol monophosphate ester (PNPP).

Chemical structure of polyoxyethylene (9) nonylphenol monophosphate ester (PNPP).

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The aim of this study was to develop and evaluate a zeta potential changing nanoemulsion (NE) containing polyoxyethylene (9) nonylphenol monophosphate ester (PNPP) as emulsifier. 2% (v/v) of PNPP and 0.18% (5 μM) of cetyltrimethylammonium bromide (CTAB) were incorporated into the lipophilic NE preconcentrate (PEG-40 castor oil, glyceryl tricaprylat...

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... purpose of this study was therefore to develop a zeta potential changing system based on a different phosphorylated surfactant exhibiting a PEG spacer. To achieve this goal, polyoxyethylene (9) nonylphenol monophosphate ester (PNPP), as illustrated in Fig. 1, was incorporated in a NE. The resulting formulation should demonstrate a reduced cytotoxicity compared to previous systems including substances such as POAP due to the lack of a positive charged molecule moiety. Furthermore, the single-chain hydrophilic PEG linker of PNPP might enable a more efficient phosphate cleavage by IAP leading ...

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... Before further experiments, we first studied the effect of HEMAPE on the dispersion behaviors of modified resin in water by evaluating particle size and Zeta potential value [28][29][30] . Table 1 shows the particle size of the water-borne modified resin dispersion, which is observed to decrease with the HEMAPE content. ...
Article
There is a growing interest in environmentally friendly coatings from the paint and coating industries, with water-borne acrylic-epoxy ester hybrid resins emerging as prominent candidates. Despite their eco-friendliness, these resins exhibit poor mechanical and anti-corrosion properties. These two essential properties can be improved by grafting new functional materials into the hybrid resin. In this work, we introduced a novel phosphate ester functional monomer (hydroxyethyl methacrylate ethyl phosphate (HEMAPE)) to a traditional water-borne acrylic-epoxy esters through free radical polymerization. Initial results reveal a substantial enhancement in the dispersion stability of the modified water-borne acrylic-epoxy esters in aqueous environments. The cured coating derived from this modification significantly improves the mechanical strength and anti-corrosion characteristics of the coating. Notably, X-ray Photoelectron Spectroscopy (XPS) analysis further explains the improved performance whereby it confirms the formation of phosphate chelates within the cured modified coatings, facilitated by HEMAPE, which effectively chelates with metallic ions originating from the corrosion products on the steel substrate. These chelates adhere to the metal surface, impeding further corrosion reactions and thereby optimizing the corrosion protection performance of the coating. This modification approach, characterized by its simplicity of preparation and overall improved coating performance, could be employed in paints for metal corrosion protection.
... Interestingly, LNP THAB showed two times higher phosphate release than LNP DOTAP which differs from the results found during incubation with the enzyme itself. As a control, PIC2 was added to the samples inhibiting the membrane bound enzyme and significantly lower phosphate release was detected which is in confirmation with other studies [19,20,41]. ...
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It was the aim of this study to design charge converting lipid nanoparticles (LNP) via a microfluidic mixing technique used for the preparation and coating of LNP. LNP consisting of 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), cholesterol, N-(carbonyl-methoxypolyethyleneglycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine (MPEG-2000-DSPE), and various cationic surfactants were prepared at diverging flow rate ratios (FRR) via microfluidic mixing. Utilizing a second chip in the microfluidic set-up, LNP were coated with polyoxyethylene (9) nonylphenol monophosphate ester (PNPP). LNP were examined for their stability in different physiologically relevant media as well as for hemolytic and cytotoxic effects. Finally, phosphate release and charge conversion of PNPP-coated LNP were evaluated after incubation with alkaline phosphatase and on Caco2-cells. LNP produced at an FRR of 5:1 exhibited a size between 80 and 150 nm and a positive zeta potential. Coating with PNPP within the second chip led to LNP exhibiting a negative zeta potential. After incubation with 1 U/ml alkaline phosphatase for 4 h, zeta potential of the LNP containing 1,2-dioleoyloxy-3-trimethylammonium-propane chloride (DOTAP) as cationic component shifted from − 35 mV to approximately + 5 mV. LNP prepared with other cationic surfactants remained slightly negative after enzymatic phosphate cleavage. Manufacturing of LNP containing PNPP and DOTAP via connection of two chips in a microfluidic instrument proves to show efficient change in zeta potential from negative to positive after incubation with alkaline phosphatase. Graphical abstract
... Another strategy for achieving a shift in zeta potential besides cleavage of phosphate groups of corresponding surfactants is the addition of cationic excipients, such as cetyltrimethylammonium bromide (Akkuş-Dagdeviren et al., 2021, Kurpiers et al., 2020. These tools are bearing herewith the potential risk of increasing toxicity (Lam et al., 2019) dependent on a positive net charge resulting in lower permeation properties being already immobilized on the way to the targeted tissue via ion interactions with the negatively charged cell membrane outlining hence the polycation (Bernkop-Schnürch, 2018) aside from the before mentioned PEG dilemma (Pozzi et al., 2014). ...
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Aim: This study aims to design and evaluate zeta potential shifting nanoemulsions comprising single and gemini type tyrosine-based surfactants for specific cleavage by tyrosine phosphatase. Methods: Tyrosine-based surfactants, either single 4-(2-amino-3-(dodecylamino)-3-oxopropyl)phenyl dihydrogen phosphate (AF1) or gemini 4-(2-amino-3-((1-(dodecylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)amino)-3-oxopropyl)phenyl dihydrogen phosphate (AF2) type were synthesized via amide bond formation of tyrosine with dodecylamine followed by phosphorylation. These surfactants were incorporated into nanoemulsions. Nanoemulsions were monitored by incubation with isolated tyrosine phosphatase as well as secreted tyrosine phosphatase of Escherichia coli in terms of phosphate release and zeta potential change. Results: Via isolated tyrosine phosphatase, and mediated by Escherichia coli, phosphate groups of either single or gemini tyrosine-based surfactants could be cleaved by secreted tyrosine phosphatase. Nanoemulsions comprising a single tyrosine-based surfactant resulted in a charge shift from - 13.46 mV to - 4.41 mV employing isolated tyrosine phosphatase whilst nanoemulsions consisting of a gemini tyrosine-based surfactant showed a shift in zeta potential from - 15.92 mV to - 5.86 mV, respectively. Conclusion: Nanoemulsions containing tyrosine-based surfactants represent promising zeta potential shifting nanocarrier systems targeting tyrosine phosphatase secreting bacteria.
... Globules with zeta potentials greater than +30 mV and lower than −30 mV are usually considered stable [39]. Zeta potentials greater than either +60 mV or −60 mV characterize exceptionally stable nanoemulsions [40]. ...
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The second most significant cause of cancer-related mortality and morbidity in the United States is colorectal cancer (CRC), the third most diagnosed malignancy. People over 50 have an increased risk of CRC everywhere in the world. Genetic and environmental risk factors significantly influence CRC development. Early detection is critical in the treatment and prevention of CRC. The population's incidence rate of CRC is currently reduced by screening techniques and medicines, although recurrence of the disease may result from the cancer's ability to spread locally. Consequently, the difficulty is in finding a different treatment for CRC. Nanotechnology is crucial for cancer treatment because it allows for the delivery of targeted chemotherapies to cancer cells directly and with greater therapeutic potency. Nanoemulsions have broad application in pharmaceutics, cosmetics, and food; their outstanding properties include enhanced dispersion of active hydrophobic components, small size, high surface area per unit volume, and improved absorption in cancer treatment. The present review highlights formulation aspects, preparation methods, and characterization techniques. We also provide a critical analysis of recent developments in nanoemulsions in colorectal cancer treatment that hold promise in delivering nanoemulsions in colorectal treatment.
... It is significant to examine the stability of nanocomposite in a medium to consider its complementary effect. Accumulation and stability depend on the charge of the nanoparticles [53]. ...
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The present study aims to synthesize and characterize eugenol-loaded nanocomposite (using Syzygium aromaticum), followed by drug loading and analysis of drug release kinetics using standard procedure. UV–Vis spectroscopy showed absorption band at 258 nm, FTIR revealed the availability of eugenol, and SEM analysis and X-ray diffractometer examination revealed average particle diameter of 42.67 nm with orthorhombic structure. Energy dispersive X-ray (EDAX), Zeta, and size distribution pattern also confirmed the elemental composition, formation of stable nanocomposite, and uniformity of synthesized nanocomposite, respectively. MIC value obtained for Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa was 6.25 μg/ml, and for Proteus mirabilis, it is 3.25 μg/ml. MBC value for Escherichia coli and Proteus mirabilis was 12.5 μg/ml, and for Staphylococcus aureus and Pseudomonas aeruginosa, it was 25 μg/ml. Antioxidant studies revealed that Eu@NC showed significant DPPH free radical scavenging activity. This biosynthesized Eu@NC with enhanced antibacterial activity could be less toxic to environment and an eco-friendly approach. Graphical Abstract Preparation of powdered clove buds and extraction of phytochemicals, visible changes in the salt solution after addition of plant extract, eugenol loading through Sonicator, characterization and analysis of drug release kinetics, evaluation of antibacterial and antioxidant activity.
... Zeta potential with positive or negative 30 mV (±30 mV) as the average value was considered an arbitrary value, separating low-charged surfaces from highly charged surfaces (Ho et al., 2020;Nandy et al., 2022;Preetz et al., 2010). Zeta potential >±30 mV indicates stable nanoemulsion, while values ranging between 0.00 -±30 mV indicate unstable nanoemulsion (Ho et al., 2020;Kurpiers et al., 2020;Nandy et al., 2022). We obtained a single peak in each DLS analysis for samples 2C or 6C, indicating the high quality of these nanoemulsions (Khan and Ramalingam, 2019;Oliveira et al., 2017). ...
Article
Controlling vector borne disease insects control such as mosquitoes and reducing the use of synthetic insecticides is a major public health challenge. Green nanoinsecticides are suitable alternatives to synthetic insecticides, enabling effective and safer insect control. This study aimed to develop neem oil-based nanoemulsions using Tween 80 and/or gum arabic (GA) as a natural emulsifiers and to study their larvicidal, and adulticidal activity against Culex pipiens larvae. The fatty acids in the oils were identified using gas chromatographs-mass spectrometry (GC-MS). We also studied the acute oral toxicity on male rats and its ecotoxicological effects using the Microtox® assay. We fabricated neem oil nanoemulsions with and without GA at different ratios and performed physicochemical, stability, and characterization studies. The results showed that the major fatty acids in neem oil were oleic acid (44.79%), linoleic acid (18.41%), palmitic acid (18%), and stearic acid (16.64%). We created two highly stable nanoemulsions, i.e., samples 2C and 6C with a droplet sizes of 87.4 and 146.7 nm by mixing neem oil, GA, and Tween 80 at a ratio of 1:0:1.5, and 1:1.5:0, respectively, followed by high-speed homogenization for 10 min. The lethal concentration (LC50) of neem oil, 2C and 6C were 9.36, 6.45, and 8.01 μg/ml for the Culex pipiens larvae and 21.7, 8.8 and 17.2 μg/ml for the adults. The toxicity time (T50) was 40.7, 10.0, and 28.9 min for normal neem oil, samples 2C and 6C, respectively. The nanoemulsions altered the toxifying-detoxifying enzymes acetylcholinesterase (AChE) and glutathione S-transferase (GST) without showing any toxicity in the male rats or the Microtox assay. The neem oil nanoformulations with Tween 80 or GA were highly stable and effective against larval and adult Culex pipiens. GA is a natural-surfactant and hence, is excellent emulsifier alternative to synthetic surfactants. The nanoemulsions did not display any toxic and eco-toxic effects. Therefore, these nanoemulsions can be considered potential alternatives to synthetic insecticides for controlling vector-borne disease insects.
... Phosphatase inhibitors are often used in various in vitro studies especially on cultured cell models and on freshly excised tissue to evaluate the impact of ALP on the performance of phosphate functionalized DDS. [7,81,103,104] Performing cellular uptake studies of phosphorylated NCs with and without inhibition of ALP, for instance, can show the effect of this enzyme on the performance of these delivery systems as depicted in Figure 4. Table 2 lists some common inhibitors and activators of various isotypes of ALP as well as their proposed mechanism. ...
... In order to eliminate the toxic effects derived from tertiary amine structure of POAP, Kurpiers et al. used polyoxyethylene (9) nonylphenol monophosphate ester (PNPP) as phosphorylated surfactant and upon incubation with bovine intestinal ALP within 4 h 92% of total phosphate was cleaved off which is almost twofold higher than POAP. [104] Apart from the formulation-related factors for this enhancement, structure differences of the surfactants are playing an important role. Due to double-chain structure of POAP, a steric hindrance might take place leading to an increased phosphate release in the case of PNPP having a single PEG chain (Table 4). ...
... This corona effect was shown by Zaichik et al., as in the absence of PEGylated emulsifiers zeta potential changes of Δ40 mV upon contact with ALP were measured whereas nanoemulsions containing polyethoxylated-35 castor oil remained constant without any significant change in zeta potential due to the hindrance of PA. [213] Furthermore, a significant amount of phosphate was released from DOCP liposomes upon incubation with ALP due to absence of such a PEG corona on the surface. [214] In order to overcome PEG-corona, phosphorylated surfactants with PEG spacer arms were utilized and Δ21.6 mV and Δ41.9 mV changes in zeta potential were achieved for POAP [218] and PNPP [104] containing formulations, respectively. Further evidence was provided by comparing the phosphate release efficiency of phosphorylated surfactants having been incorporated into SEDDS as illustrated in Figure 12 upon ALP treatment. ...
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Since the 1960s the membrane‐bound enzyme alkaline phosphatase (ALP) has been utilized in drug delivery. As it cleaves phosphate substructures from drugs, auxiliary agents, and even from the surface of nanocarriers, this enzyme enables the design of drug delivery systems that can alter their properties in the body on demand. Anionic nanocarriers exhibiting bioinert properties can alter their surface to interactive once having reached the target site as due to an ALP‐triggered cleavage of anionic phosphate groups from their surface charge converts to cationic improving for instance cellular uptake. Moreover, features such as the accumulation of nanocarriers at the target site or a targeted drug release triggered by ALP can be introduced. In addition, ALP is utilized to improve the potential of numerous diagnostic systems. Within this review, one provides an overview about the activity, selectivity, and distribution of this enzyme, as well as the great variety of applications in drug delivery and diagnostics making use of it.
... 12 Therefore, a zeta potential value higher than 30 mV (positive or negative) induces the surface area to prevent aggregation between particles and ensure a stable emulsion. 13 The result showed the zeta potential of nutmeg oil nanoemulsion ranged from (-) 16 concentration of 30 percent also had a zeta potential higher than 30 but not significantly different from the span 60-tween 80 mixed surfactants. Furthermore, the mixture of spans 60-tween 80 also showed a decreasing trend with increased concentration with no significant difference. ...
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The application of essential oil is limited due to its low solubility, especially in water-based products. Using a nanoemulsion as a carrier is one way to overcome this disadvantage. Nanoemulsion is composed of the water phase, oil phase, surfactant, and cosurfactant. The use of a mixture of surfactants can affect the stability of the nanoemulsion. The aim of this research, therefore, is to find out the effect of the type and concentration of the mixture of surfactant and protein on the stability of nutmeg oil nanoemulsion. A Randomized Block Design (RBD) Factorial with 2 variables, which included the type (gelatin-span 60, gelatin-tween 80, span 60-tween 80) and concentration (20, 25, and 30 percent) of mixed surfactants and protein counts from the total oil was used with 1:1 comparison. The result showed there was a span of 60-tween 80 produced a nanoemulsion with the finest stability considering its creaming index value of 0%, the small droplet size of 95.88 nm, zeta potential value higher than -30 mV, and good uniformity less than 0.1 in polydispersity index. Gelatin-span 60 failed to produce an emulsion with nano-size due to its 2300.55 nm droplet size, zeta potential value less than 30 mV, and its uniformity in polydispersity index of more than 0.1.
... Zeta potential values provide the information about the homogenous behavior of the nano-emulsion. Particles with zeta potential more positive than + 30 mV or more negative than -30 mV are usually considered to be stable, since electrical charge of droplets is strong enough to assume that repulsive forces between droplets are predominant in the nanoemulsion [39]. The surface of NE was negatively charged with an average zeta potential (− 30 and − 40 mV) which indicates that the formulation is stable. ...
Research
Although safe and eco-friendly botanical pesticides have been intensively promoted to combat pest attacks in agriculture, but their stability and efficacies remain an issue for their wide acceptability as sustained and effective approaches. The purpose of this work was to develop stable neem oil based nano-emulsion (NE) formulation with enhanced activity employing suitable bio-inspired adjuvant. So, Neem NEs (with and without) natural adjuvants (Cymbopogon citratus and Prosopis juliflora) in different concentrations were prepared and quality parameters dictating kinetic stability, acidity/alkalinity, viscosity, droplet size, zeta potential, surface tension, stability and compatibility were monitored using Viscometer, Zetasizer, Surface Tensiometer, High Performance Liquid Chromatography (HPLC) and Fourier Transform Infrared Spectroscopy (FTIR). Nanoemulsion biosynthesis optimization studies suggested that slightly acidic (5.9–6.5) NE is kinetically stable with no phase separation; creaming or crystallization may be due to botanical adjuvant (lemongrass oil). Findings proved that Prosopis juliflora, acted as bio-polymeric adjuvant to stabilize NE by increasing Brownian motion and weakening the attractive forces with smaller droplets (25–50 nm), low zeta potential (􀀀 30 mV) and poly-dispersive index (<0.3). Botanical adjuvant (30%) based NE with optimum viscosity (98.8cPs) can give long term storage stability and improved adhesiveness and wetting with reduced surface tension and contact angle. FT-IR analysis assured azadirachtin’s stability and compatibility with adjuvant. With negligible degradation (1.42%) and higher half-life (t1/2) of 492.95 days, natural adjuvant based NE is substantially stable formulation, may be due to presence of glycosidic and phenolics compounds. Neem 20NE (with 30% adjuvant) exhibited remarkable insecticidal activity (91.24%) against whitefly (Bemisia tabaci G.) in brinjal (Solanum melongena) as evidenced by in-vivo assay. Results thus obtained suggest, bio-pesticide formulation may be used as safer alternative to chemical pesticides to minimize pesticide residues and presence of natural adjuvant may improves the stability and efficacy of biopesticides for safe crop protection in organic agriculture and Integrated Pest Management.
... Zeta potential values provide the information about the homogenous behavior of the nano-emulsion. Particles with zeta potential more positive than + 30 mV or more negative than -30 mV are usually considered to be stable, since electrical charge of droplets is strong enough to assume that repulsive forces between droplets are predominant in the nanoemulsion [39]. The surface of NE was negatively charged with an average zeta potential (− 30 and − 40 mV) which indicates that the formulation is stable. ...
Article
Although safe and eco-friendly botanical pesticides have been intensively promoted to combat pest attacks in agriculture, but their stability and efficacies remain an issue for their wide acceptability as sustained and effective approaches. The purpose of this work was to develop stable neem oil based nano-emulsion (NE) formulation with enhanced activity employing suitable bio-inspired adjuvant. So, Neem NEs (with and without) natural adjuvants (Cymbopogon citratus and Prosopis juliflora) in different concentrations were prepared and quality parameters dictating kinetic stability, acidity/alkalinity, viscosity, droplet size, zeta potential, surface tension, stability and compatibility were monitored using Viscometer, Zetasizer, Surface Tensiometer, High Performance Liquid Chromatography (HPLC) and Fourier Transform Infrared Spectroscopy (FTIR). Nano-emulsion biosynthesis optimization studies suggested that slightly acidic (5.9-6.5) NE is kinetically stable with no phase separation; creaming or crystallization may be due to botanical adjuvant (lemongrass oil). Findings proved that Prosopis juliflora, acted as bio-polymeric adjuvant to stabilize NE by increasing Brownian motion and weakening the attractive forces with smaller droplets (25-50 nm), low zeta potential (-30mV) and poly-dispersive index (<0.3). Botanical adjuvant (30%) based NE with optimum viscosity (98.8cPs) can give long term storage stability and improved adhesiveness and wetting with reduced surface tension and contact angle. FT-IR analysis assured azadirachtin’s stability and compatibility with adjuvant. With negligible degradation (1.42%) and higher half-life (t1/2) of 492.95 days, natural adjuvant based NE is substantially stable formulation, may be due to presence of glycosidic and phenolics compounds. Neem 20NE (with 30% adjuvant) exhibited remarkable insecticidal activity (91.24%) against whitefly (Bemisia tabaci G.) in brinjal (Solanum melongena) as evidenced by in-vivo assay. Results thus obtained suggest, bio-pesticide formulation may be used as safer alternative to chemical pesticides to minimize pesticide residues and presence of natural adjuvant may improves the stability and efficacy of biopesticides for safe crop protection in organic agriculture and Integrated Pest Management.