Poloxamer 407

Last updated
Poloxamer 407
Poloxamere General Formula V2.svg
Skeleton formula of poloxameres, where poloxamer 407 has block lengths of a = 101 and b = 56
Names
IUPAC name
Oxirane, methyl-, polymer with oxirane
Other names
  • Pluronic F-127
  • Synperonic PE/F-127
  • Kolliphor P 407
  • Poloxalene
Identifiers
DrugBank
PubChem CID
UNII
Properties
C
572
H
1146
O
259
Molar mass 12,600 g/mol
Appearancewhite powder
Melting point 53–57 °C (127–135 °F; 326–330 K)
very soluble
Hazards
NFPA 704 (fire diamond)
0
1
0
Safety data sheet (SDS) Kolliphor P 407
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Poloxamer 407 is a hydrophilic non-ionic surfactant of the more general class of copolymers known as poloxamers. Poloxamer 407 is a triblock copolymer consisting of a central hydrophobic block of polypropylene glycol flanked by two hydrophilic blocks of polyethylene glycol (PEG). The approximate lengths of the two PEG blocks is 101 repeat units, while the approximate length of the propylene glycol block is 56 repeat units. [1] This particular compound is also known by the BASF trade name Pluronic F-127 or by the Croda trade name Synperonic PE/F 127. BASF also offers a pharmaceutical grade, under trade name Kolliphor P 407. [2]

Contents

Uses

Most of the common uses of poloxamer 407 are related to its surfactant properties. For example, it is widely used in cosmetics for dissolving oily ingredients in water. It can also be found in multi-purpose contact lens cleaning solutions, where its purpose there is to help remove lipid films from the lens. It can also be found in some mouthwashes. There is research ongoing for using poloxamer 407 for aligning severed blood vessels before gluing them surgically. [3] Poloxamer 407 can also be used for its thermogelling properties in aqueous media.

Poloxamer 407 is approved by the FDA for use as an excipient in a range of pharmaceutical dosage forms, and is listed in the Inactive Ingredient Database (IID). [4]

Poloxamer 407 is used in bioprinting applications due to its unique phase-change properties. [5] In a 30% solution by weight, poloxamer 407 forms a gel solid at room temperature but liquifies when chilled to 4 °C (39 °F). This allows poloxamer 407 to serve as a removable support material, particularly for creating hollow channels or cavities inside hydrogels. [6] [7] In this role, it is often referred to as a "sacrificial ink" or a "fugitive ink".

Reports of adverse effects

It was reported in The Australian newspaper 18 November 2006 that this common ingredient in toothpaste and mouthwash can cause high cholesterol in mice. [8] A team from the Centre for Ageing and the ANZAC Research Institute in Sydney used it as a tool to demonstrate that cells in the liver behave like a sieve. They gave a high dose (1 gram per kilogram of body weight) of poloxamer 407 to mice, which blocked 80% of the pores in liver cells that absorb lipoproteins, leading to a 10-fold increase in plasma lipid levels. [9] However, the dose used is far higher than a person would be exposed to in toothpaste or mouthwash.

Potential degradation by sonication

Wang et al. [10] reported that aqueous solutions of poloxamer 188 and poloxamer 407 sonicated in the presence or absence of multi-walled carbon nanotubes (MWNTs) can become highly toxic to cultured cells. The toxicity correlated with the sonolytic degradation of the polymers.

Related Research Articles

High-density lipoprotein (HDL) is one of the five major groups of lipoproteins. Lipoproteins are complex particles composed of multiple proteins which transport all fat molecules (lipids) around the body within the water outside cells. They are typically composed of 80–100 proteins per particle and transporting up to hundreds of fat molecules per particle.

Polyvinylpyrrolidone Water-soluble polymer

Polyvinylpyrrolidone (PVP), also commonly called polyvidone or povidone, is a water-soluble polymer made from the monomer N-vinylpyrrolidone. PVP is available in a range of molecular weights and related viscosities, and can be selected according to the desired application properties.

Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an organic compound with the formula CH3(CH2)11OSO3Na. It is an anionic surfactant used in many cleaning and hygiene products. This compound is the sodium salt of the 12-carbon an organosulfate. Its hydrocarbon tail combined with a polar "headgroup" give the compound amphiphilic properties and so make it useful as a detergent. SDS is also component of mixtures produced from inexpensive coconut and palm oils. SDS is a common component of many domestic cleaning, personal hygiene and cosmetic, pharmaceutical, and food products, as well as of industrial and commercial cleaning and product formulations.

Lipoprotein Biochemical assembly whose purpose is to transport hydrophobic lipid molecules

A lipoprotein is a biochemical assembly whose primary function is to transport hydrophobic lipid molecules in water, as in blood plasma or other extracellular fluids. They consist of a triglyceride and cholesterol center, surrounded by a phospholipid outer shell, with the hydrophilic portions oriented outward toward the surrounding water and lipophilic portions oriented inward toward the lipid center. A special kind of protein, called apolipoprotein, is embedded in the outer shell, both stabilising the complex and giving it a functional identity that determines its role.

Surfactant Substance that lowers the surface tension between a liquid and another material

Surfactants are compounds that lower the surface tension between two liquids, between a gas and a liquid, or between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming agents, or dispersants. The word "surfactant" is a blend of surface-active agent, coined c.  1950.

Polyethylene glycol Chemical compound

Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular weight. The structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH.

Toothpaste Paste, gel dentifrice or tablet used to clean and maintain the health of teeth

Toothpaste is a paste or gel dentifrice used with a toothbrush to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from the teeth, assists in suppressing halitosis, and delivers active ingredients to help prevent tooth decay and gum disease (gingivitis). Owing to differences in composition and fluoride content, not all toothpastes are equally effective in maintaining oral health. The decline of tooth decay during the 20th century has been attributed to the introduction and regular use of fluoride-containing toothpastes worldwide. Large amounts of swallowed toothpaste can be toxic. Common colors for toothpaste include white and blue.

Micelle Group of fatty molecules suspended in liquid by soaps and/or detergents

A micelle or micella is an aggregate of surfactant phospholipid molecules dispersed in a liquid, forming a colloidal suspension. A typical micelle in water forms an aggregate with the hydrophilic "head" regions in contact with surrounding solvent, sequestering the hydrophobic single-tail regions in the micelle centre.

Benzalkonium chloride Surfactant and antiseptic agent

Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

Ezetimibe Medication used to treat high cholesterol

Ezetimibe is a medication used to treat high blood cholesterol and certain other lipid abnormalities. Generally it is used together with dietary changes and a statin. Alone, it is less preferred than a statin. It is taken orally. It is also available in the fixed combinations ezetimibe/simvastatin, ezetimibe/atorvastatin, and ezetimibe/rosuvastatin.

Ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.

Amphiphile Hydrophilic and lipophilic chemical compound

An amphiphile is a chemical compound possessing both hydrophilic and lipophilic (fat-loving) properties. Such a compound is called amphiphilic or amphipathic. Common amphiphilic substances are soaps, detergents, and lipoproteins. The phospholipid amphiphiles are the major structural component of cell membranes.

Polysorbate 80 Nonionic surfactant and emulsifier used in food and cosmetics

Polysorbate 80 is a nonionic surfactant and emulsifier often used in pharmaceuticals, foods, and cosmetics. This synthetic compound is a viscous, water-soluble yellow liquid.

Polysorbate 20 is a polysorbate-type nonionic surfactant formed by the ethoxylation of sorbitan monolaurate. Its stability and relative nontoxicity allows it to be used as a detergent and emulsifier in a number of domestic, scientific, and pharmacological applications. As the name implies the ethoxylation process leaves the molecule with 20 repeat units of polyethylene glycol; in practice these are distributed across 4 different chains, leading to a commercial product containing a range of chemical species.

Benzethonium chloride Chemical compound

Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties, and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.

Poloxamers are nonionic triblock copolymers composed of a central hydrophobic chain of polyoxypropylene flanked by two hydrophilic chains of polyoxyethylene. The word poloxamer was coined by BASF inventor, Irving Schmolka, who received the patent for these materials in 1973. Poloxamers are also known by the trade names Pluronic, Kolliphor, and Synperonic.

Sodium lauroyl sarcosinate (INCI), also known as sarkosyl, is an anionic surfactant derived from sarcosine used as a foaming and cleansing agent in shampoo, shaving foam, toothpaste, and foam wash products.

Pluronic P123 is a symmetric triblock copolymer comprising poly(ethylene oxide) (PEO) and poly(propylene oxide) (PPO) in an alternating linear fashion, PEO-PPO-PEO. The unique characteristic of PPO block, which is hydrophobic at temperatures above 288 K and is soluble in water at temperatures below 288 K, leads to the formation of micelle consisting of PEO-PPO-PEO triblock copolymers. Some studies report that the hydrophobic core contains PPO block, and a hydrophilic corona consists of PEO block. In 30wt% aqueous solution Pluronic P123 forms a cubic gel phase.

Niosome

A niosome is a non-ionic surfactant-based vesicle. Niosomes are formed mostly by non-ionic surfactant and cholesterol incorporation as an excipient. They are structurally similar to liposomes as they both have a bilayer. However, the materials used to prepare niosomes are what make them more stable. They can entrap both hydrophilic and lipophilic drugs, either in an aqueous layer or in a vesicular membrane made of lipid material.

Wetting solution

Wetting solutions are liquids containing active chemical compounds that minimise the distance between two immiscible phases by lowering the surface tension to induce optimal spreading. The two phases, known as an interface, can be classified into five categories, namely, solid-solid, solid-liquid, solid-gas, liquid-liquid and liquid-gas.

References

  1. Tania Betancourt; The University of Texas at Austin. Biomedical Engineering (2007). Targetable biodegradable nanoparticles for delivery of chemotherapeutic and imaging agents to ovarian cancer. ProQuest. pp. 130–. ISBN   978-0-549-34761-3 . Retrieved 16 August 2011.
  2. "Poloxamers for Pharmaceutical Applications". BASF Pharma. Retrieved 2022-06-11.
  3. Stanford University Medical Center (28 August 2011). "Sutureless method for joining blood vessels invented". ScienceDaily.
  4. "Inactive Ingredient Search for Approved Drug Products". www.accessdata.fda.gov. Retrieved 2022-06-11.
  5. Gopinathan, Janarthanan (2018). "Recent trends in bioinks for 3D printing". Biomaterials Research. 22 (1): 11. doi:10.1186/s40824-018-0122-1. PMC   5889544 . PMID   29636985.
  6. Homan, Kimberly A.; Lewis, Jennifer A (2016). "Bioprinting of 3D Convoluted Renal Proximal Tubules on Perfusable Chips". Scientific Reports. 6: 34845. doi:10.1038/srep34845. PMC   5057112 . PMID   27725720.
  7. Kang, Hyun-Wook; Atala, Anthony (2016). "A 3D bioprinting system to produce human-scale tissue constructs with structural integrity". Nature Biotechnology. 34 (3): 312–9. doi:10.1038/nbt.3413. PMID   26878319.
  8. O'Neill, Craig (18 November 2006). "Dental hygiene gives you a brush with cholesterol". The Australian.
  9. Cogger, VC; Hilmer, SN; Sullivan, D; Muller, M; Fraser, R; Le Couteur, DG (December 2006). "Hyperlipidemia and surfactants: the liver sieve is a link". Atherosclerosis. 189 (2): 273–81. doi:10.1016/j.atherosclerosis.2005.12.025. PMID   16458315.
  10. Wang, Ruhung; Hughes, Tyler; Beck, Simon; Vakil, Samee; Li, Synyoung; Pantano, Paul; Draper, Rockford K. (2013). "Generation of toxic degradation products by sonication of Pluronic® dispersants: implications for nanotoxicity testing". Nanotoxicology. 7 (7): 1272–1281. doi:10.3109/17435390.2012.736547. ISSN   1743-5390. PMC   3657567 . PMID   23030523.