Tween 80——“Star” Surfactant

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Polysorbates (Tween, PS) are a family of amphiphilic nonionic surfactants, among which polysorbate 80 (Tween 80) is the most widely used “star” surfactant in biopharmaceutical preparations, which can prevent protein denaturation, aggregation, surface adsorption and flocculation under storage and transportation conditions. Tween 80 is a mixture, the main component of which is polyoxyethylene sorbitan monooleate.

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What is Tween 80?

Tween 80, also known as polysorbate 80, has a chemical name of polyoxyethylene 20 sorbitan monooleate. It is a light yellow to orange viscous liquid, a hydrophilic nonionic surfactant, and one of the commonly used excipients in pharmaceutical preparations. Due to its long carbon chain structure, it has a good solubilizing effect on lipophilic drugs. It is often used as a solubilizing agent, emulsifier, and stabilizer when preparing poorly soluble drug preparations.

In the past, people believed that Tween 80 only played the role of an excipient in the preparation. Recent studies have found that Tween 80 has a variety of biological and pharmacological activities, including anti-tumor activity. Some researchers have used Tween 80 and other poorly soluble drugs to make nanoparticles so that they can pass through the blood-brain barrier to treat some brain tumors.

Tween 80 can be degraded through oxidation and hydrolysis pathways, in which the hydrolysis reaction is chemically induced or enzyme-catalyzed, and the oxidation reaction is generally chemically induced. Tween 80 is used as a protective excipient for biological preparations, but it may also affect the quality of protein preparations, thereby adversely affecting efficacy, safety and stability. Currently, drug regulatory authorities are increasingly stringent in their control requirements for Tween 80.

Pharmacological Activity

Acute hypersensitivity reaction
In clinical practice, intravenous injection of injections containing Tween 80, such as etoposide injection and docetaxel injection, often leads to acute hypersensitivity reactions, especially docetaxel injection, with an early incidence rate of 5% to 40% (severe cases are classified as Class II or above according to the allergy criteria set by the National Cancer Institute in the United States, which is rare). Preoperative administration of glucocorticoids and antihistamines can effectively improve this condition. It is speculated that it is related to the release of oleic acid through hydrolysis in the body. Research has shown that oleic acid can promote histamine release in dogs and cause acute hypersensitivity reactions. Research has also been conducted domestically on the allergic effects of traditional Chinese medicine injections containing Tween 80 on dogs.
Peripheral neurotoxicity
American scientists have found through research on the effects of paclitaxel anti-tumor drugs on the nervous system that Tween 80 may cause degeneration of cystic cells, leading to peripheral neurotoxicity. The reason for this adverse reaction may be the polyethylene compounds produced by the reaction between polyol compounds in Tween 80 and ethylene oxide.
Inhibition of P-glycoprotein activity
P-glycoprotein plays an important role in active drug transport, and Tween 80 can form large micelles in blood and body fluids to encapsulate or embed protein molecules, inhibiting P-glycoprotein’s participation in drug transport at the biofilm interface.
Intrinsic anti-tumor effect
Tween 80 showed certain anti-tumor activity in model animals, which may be related to the release of oleic acid. Research data shows that oleic acid can inhibit the production of peroxides in the body and interfere with the growth of tumor cells.
Hepatotoxicity and others

Advantages of Tween 80

PS80 is the most commonly used surfactant in biologics and is used as a protein stabilizer in most commercial therapeutic protein formulations. This is due to the following factors:

High biocompatibility
Low toxicity
Effective protein stabilization. Even at low concentrations (0.1-1.0 mg/ml is commonly used in biologics), they provide sufficient protein stability. This is due to the high hydrophilic-lipophilic balance (HLB) value and low critical micelle concentration (CMC) of PS80, which is only 1.4*10-2 g/L.

Proteins are naturally unstable and are easily affected by external conditions such as temperature, vibration, shear force, buffer system and ionic strength, and even changes in their own protein concentration or purity. Among all the problems of protein denaturation and degradation, aggregation is particularly serious. Tween 80 is often used as a protein protectant in downstream formulation development. The mechanism of polysorbate stabilization of proteins is generally considered to be the two main mechanisms of interface competition and surfactant-protein complexation.

Tween 80 stabilizes proteins mainly through interfacial competition. The surface activity of Tween 80 is much higher than that of proteins (i.e. monoclonal antibodies (mAbs)). Therefore, Tween 80 can competitively occupy the interface position, inhibit protein adsorption to the air-liquid interface, thereby reducing oxidation or aggregation caused by contact with air, and effectively preventing protein from unfolding at the interface during the manufacturing process, sample handling and storage.

Tween 80 can also increase the colloidal stability of proteins by directly interacting with them. Antibodies may form aggregates through their intermolecular water transport. Tween 80 can prevent protein aggregation and even particle formation by interacting with the hydrophobic surface of proteins.

What are the Differences in Between Tween 80 and Tween 20?

Tween is a series of esters created by sorbitol and various higher fatty acids. Tween 80 is oleate and Tween 20 is laurate. Both have emulsifying results. When using, you need to choose the appropriate model according to the purpose.

Different synthetic resources

Tween 80 artificial basic materials
It is made by the polymerization of dehydrated sorbitan monooleate and ethylene oxide.
Tween 20 synthetic raw materials
It is a blend of polyoxyethylene dehydrated sorbitan monolaurate and a part of polyoxyethylene disohydrated sorbitan monolaurate.

Different properties

Tween 80 residential properties
The peroxide worth of Tween 80 does not surpass 10. It is a light yellow to orange-yellow viscous fluid with a minor smell. It tastes slightly bitter and astringent, with a warm sensation. It is quickly soluble in water, ethanol, methanol or ethyl acetate, and very slightly soluble in mineral oil. It is jelly-like at reduced temperature level and recoups after heating.
Properties of Tween 20
Tween 20 is a yellow or brownish-yellow clear oily liquid with an unique smell and a small bitter taste. Relative thickness 1.01, steaming point > 100 ℃, flash point 321 ℃, refractive index 1.472, thickness (25 ℃) 0.25 ~ 0.40 Pa · s. The particle consists of a lot more hydrophilic teams and is miscible with water, ethanol, methanol and ethyl acetate. It is insoluble in liquid paraffin, taken care of oil and light petroleum. 1 part of this product can be dissolved in 130 parts of cottonseed oil and 200 parts of toluene. The pH of 5% aqueous option is 5 ~ 7; the HLB value is 16.7.

Different uses

Uses of Tween 80
Tween 80 is a polyol-type nonionic surfactant and is one of the most frequently used one among polysorbates. It has significant resistance to electrolytes and strong hydrophilicity. It is extensively used in fluid, semi-solid and strong preparations as O/W emulsifier, solubilizer, wetting representative, dispersant and stabilizer. Tween 80 is extensively utilized in oil removal and transportation, medicine, cosmetics, repaint pigments, textiles, food, and pesticides. It is made use of as an emulsifier, dispersant, stabilizer, diffusant, lubricating substance, conditioner, antistatic agent, rust prevention, ending up agent, viscosity reducer, etc in cleaning agent manufacturing and metal surface area rust avoidance and cleansing. It can also be made use of as a gas chromatography fixed liquid for the separation of alcohols, ketones, esters and the splitting up of fats and hydrocarbons.
Uses of Tween 20
It is a condensation product of Span and ethylene oxide. Since there are a lot more hydrophilic teams in its molecules, polyoxyethylene, it has strong hydrophilicity and is a non-ionic detergent. It is frequently utilized as an oil-in-water (O/W) emulsifier; it can be used in combination with various other emulsifiers such as sodium lauryl sulfate or Period to boost the stability of the emulsion. It can likewise be used as a solubilizer for sure drugs. Tween 20 can also be used as a gas chromatography fixed phase (optimum operating temperature level 120 ° C) to separate and assess unstable oils, fat esters, alcohols, ketones and halides.

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References

Degradation of polysorbates 20 and 80 catalysed by histidine chloride buffer European Journal of Pharmaceutics and Biopharmaceutics

Characterization of Polysorbate Ester Fractions and Implications in Protein Drug Product Stability Mol. Pharmaceutics

Polysorbate 80 – WikiPedia

Tween 80 CAS 9005-65-6 | Look Chemical

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