Degradation of polysorbates 20 and 80 catalysed by histidine chloride buffer

Brovč, Ema Valentina; Mravljak, Janez; Šink, Roman; Pajk, Stane

doi:10.1016/j.ejpb.2020.07.010

Cited by 19 publications

(50 citation statements)

References 45 publications

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“…In P2 formulations (Figure A), PS80 is rapidly degraded and to a high extent. The degradation is linked to the histidine buffer, a known catalyst of PS oxidative degradation . SPGS-550M is also prone to the same oxidative degradation while VEDS and VEDG-2.2, on the other hand, do not seem to be susceptible to it.…”

Section: Resultsmentioning

confidence: 99%

“…The degradation is linked to the histidine buffer, a known catalyst of PS oxidative degradation. 52 SPGS-550M is also prone to the same oxidative degradation while VEDS and VEDG-2.2, on the other hand, do not seem to be susceptible to it. In P3 formulations (Figure 5B), PS80 shows minimal degradation, together with VEDG-2.2 and SPGS-550M.…”

Section: Api Stabilization Duringmentioning

confidence: 95%

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Not the Usual Suspects: Alternative Surfactants for Biopharmaceuticals

Brosig,

Cucuzza,

Serno

et al. 2023

ACS Appl. Mater. Interfaces

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Therapeutically relevant proteins naturally adsorb to interfaces, causing aggregation which in turn potentially leads to numerous adverse consequences such as loss of activity or unwanted immunogenic reactions. Surfactants are ubiquitously used in biotherapeutics drug development to oppose interfacial stress, yet, the choice of the surfactant is extremely limited: to date, only polysorbates (PS20/80) and poloxamer 188 are used in commercial products. However, both surfactant families suffer from severe degradation and impurities of the raw material, which frequently increases the risk of particle generation, chemical protein degradation, and potential adverse immune reactions. Herein, we assessed a total of 40 suitable alternative surfactant candidates and subsequently performed a selection through a three-gate screening process employing four protein modalities encompassing six different formulations. The screening is based on short-term agitation-induced aggregation studies coupled to particle analysis and surface tension characterization, followed by long-term quiescence stability studies connected to protein purity measurements and particle analysis. The study concludes by assessing the surfactant’s chemical and enzymatic degradation propensity. The candidates emerging from the screening are de novo α-tocopherol-derivatives named VEDG-2.2 and VEDS, produced ad hoc for this study. They display protein stabilization potential comparable or better than polysorbates together with an increased resistance to chemical and enzymatic degradation, thus representing valuable alternative surfactants for biotherapeutics.

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Section: Resultsmentioning

confidence: 99%

Section: Api Stabilization Duringmentioning

confidence: 95%

Not the Usual Suspects: Alternative Surfactants for Biopharmaceuticals

Brosig,

Cucuzza,

Serno

et al. 2023

ACS Appl. Mater. Interfaces

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“…Under these conditions, it can be predicted that the cloud point is exceeded. The solubility of Tween 80 decreases drastically above the cloud point temperature [28,29]. The addition of SDS to the subcritical water process showed that both factors (surfactant concentration and temperature) had a significant impact (p<0.05).…”

Section: Effect Surfactant In Subcritical Water Processmentioning

confidence: 99%

Impact of surfactant-aided subcritical water pretreatment process conditions on the reducing sugar production from oil palm empty fruit bunch

Rachmah

Fatmawati

Widjaja

2022

IOP Conf. Ser.: Earth Environ. Sci.

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Oil palm empty fruit bunch (OPEFB), waste produced from the palm oil mills, has not been intensely utilized while its abundant availability in tropical countries such as Indonesia. It is one of the potential lignocellulosic material sources which can be utilized to produce sugar. The subcritical water process has been known as a promising lignocellulose-to-sugar conversion process. This study examined the effects of temperature, surfactant types, and concentrations on the sugar yield from OPEFB through the subcritical water process. In this research, the subcritical water process was conducted at a varied temperature of 140-180 °C, constant pressure and time of 60 bar, and 60 minutes, respectively. The types of surfactants studied were non-ionic, anionic, and cationic (Tween 80, SDS, and CTAB). Reducing sugar concentration analyses and solid characterizations using SEM, XRD, FTIR, and TGA were carried out in this research to evaluate the impact of the subcritical water process variables. The experiments showed that Tween 80 addition to the subcritical water process produced significant sugar yields at temperature 140 °C. The addition of CTAB to the subcritical water process shows adverse effects, while that of SDS showed support in the sugar production yields. This may be caused by hydrophobic and hydrophilic interactions between functional groups of the lignin unit and the hydrophobic and ionic groups of the surfactants. The subcritical water process run at a temperature of 180 °C assisted by SDS is the best scenario to produce the highest reducing sugar yield of 4.034%.

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“…They appeared to be more biodegradable compared to aforementioned geminis of the betainate and esterquat types. In [38], the hydrolysis of polysorbate 20 and polysorbate 80 in buffered solutions (pH 5.5, 6.5), including histidine chloride, sodium citrate, sodium succinate and sodium phosphate buffers, was studied. For the histidine buffer showing the highest rate effect, a detailed study was carried out that revealed that (i) ester hydrolysis mainly contributed to the degradation, mediated by imidazolium residue of histidine; (ii) oxidation and aminolysis were minor processes; polysorbate 80 showed easier degradation compared to polysorbate 20; (iv) the presence of unsaturated bonds promoted the degradation, thereby indicating that all-oleate polysorbates are not beneficial components for nanocontainers; (v) the formulation admixed with monoclonal antibodies may protect surfactants against histidine catalyzed degradation.…”

Section: Nanocontainers Based On Biodegradable Surfactantsmentioning

confidence: 99%

Self-Assembling Drug Formulations with Tunable Permeability and Biodegradability

et al. 2021

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This review focuses on key topics in the field of drug delivery related to the design of nanocarriers answering the biomedicine criteria, including biocompatibility, biodegradability, low toxicity, and the ability to overcome biological barriers. For these reasons, much attention is paid to the amphiphile-based carriers composed of natural building blocks, lipids, and their structural analogues and synthetic surfactants that are capable of self-assembly with the formation of a variety of supramolecular aggregates. The latter are dynamic structures that can be used as nanocontainers for hydrophobic drugs to increase their solubility and bioavailability. In this section, biodegradable cationic surfactants bearing cleavable fragments are discussed, with ester- and carbamate-containing analogs, as well as amino acid derivatives received special attention. Drug delivery through the biological barriers is a challenging task, which is highlighted by the example of transdermal method of drug administration. In this paper, nonionic surfactants are primarily discussed, including their application for the fabrication of nanocarriers, their surfactant-skin interactions, the mechanisms of modulating their permeability, and the factors controlling drug encapsulation, release, and targeted delivery. Different types of nanocarriers are covered, including niosomes, transfersomes, invasomes and chitosomes, with their morphological specificity, beneficial characteristics and limitations discussed.

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Degradation of polysorbates 20 and 80 catalysed by histidine chloride buffer

Cited by 19 publications

References 45 publications

Not the Usual Suspects: Alternative Surfactants for Biopharmaceuticals

Not the Usual Suspects: Alternative Surfactants for Biopharmaceuticals

Impact of surfactant-aided subcritical water pretreatment process conditions on the reducing sugar production from oil palm empty fruit bunch

Self-Assembling Drug Formulations with Tunable Permeability and Biodegradability

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