Chitosan

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Chitosan is a linear polysaccharide composed of randomly distributed ß-(1-4)-linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). It has a number of commercial and possible biomedical uses.

Manufacture and properties

Chitosan is produced commercially by deacetylation of chitin , which is the structural element in the exoskeleton of crustaceans (crabs, shrimp, etc.). The degree of deacetylation (%DA) can be determined by NMR spectroscopy, and the %DA in commercial chitosans is in the range 60-100 %.

The amino group in chitosan has a pKa value of ~6.5, thus, chitosan is positively charged and soluble in acidic to neutral solution with a charge density dependent on pH and the %DA-value. In other words, chitosan is bioadhesive and readily binds to negatively charged surfaces such as mucosal membranes. Chitosan enhances the transport of polar drugs across epithelial surfaces, and is biocompatible and biodegradable. Purified qualities of chitosans are available for biomedical applications.

Chitosan and its derivatives such as trimethylchitosan (where the amino group has been trimethylated) have been used in non-viral gene delivery. Trimethylchitosan, or quaternised chitosan, has been shown to transfect breast cancer cells; with increased degree of trimethylation increasing the cytotoxicity and at approximately 50% trimethylation the derivative is the most efficient at gene delivery. Oligomeric derivatives (3-6 kDa) are relatively non-toxic and have good gene delivery properties.[1]

Usage

Chitosan is used primarily as a plant growth enhancer, and as a substance that boosts the ability of plants to defend against fungal infections. It is approved for use outdoors and indoors on many plants grown commercially and by consumers. The active ingredient is found in the shells of crustaceans, such as lobsters, crabs, and shrimp, and in certain other organisms. Given its low potential for toxicity and its abundance in the natural environment, chitosan is not expected to harm people, pets, wildlife, or the environment when used according to label directions.[2]

Chitosan can also be used in water processing engineering as a part of a filtration process. Chitosan causes the fine sediment particles to bind together and is subsequently removed with the sediment during sand filtration. Chitosan also removes phosphorus, heavy minerals, and oils from the water. Chitosan is an important additive in the filtration process. Sand filtration apparently can remove up to 50% of the turbidity alone while the Chitosan with sand filtration removes up to 99% turbidity.[3]

Chitosan is also useful in other filtration situations, where one may need to remove suspended particles from a liquid. Chitosan, in combination with bentonite, gelatin, silica gel, isinglass, or other fining agents is used to clarify wine, mead, and beer. Added late in the brewing process, chitosan improves flocculation, and removes yeast cells, fruit particles, and other detritus that cause hazy wine. Chitosan combined with colloidal silica is becoming a popular fining agent for white wines, because chitosan does not require acidic tannins (found primarily in red wines) to flocculate with.[4]

Biomedical use

Chitosan's properties allow it to rapidly clot blood, and has recently gained approval in the USA for use in bandages and other hemostatic agents. Chitosan purified from shrimp shells is used in a granular hemostatic product, Celox, made by Medtrade Biopolymers Inc. of Crewe, England and in the chitosan dressings made by HemCon Medical Technologies Inc. of Portland, OR, USA [5]. The Hemcon product reduces blood loss in comparison to gauze dressings and increases patient survival [6]. Hemcon products have been sold to the United States Army, who have already used the bandages on the battlefields of Iraq[7]. Chitosan is hypoallergenic, and has natural anti-bacterial properties, further supporting its use in field bandages.[8]

Claimed benefits

Chitosan is frequently sold in tablet form at health stores as a 'fat attractor' alongside weight-loss claims that it can attract fat from the digestive system and expel it from the body. There is no evidence to support this claim.

External links

  • [2] Jamie Fritch's take on chitosan
  • The Chitosanase Web Page – dedicated to the enzymatic hydrolysis of chitosan.
  • ScienCentral News "But now, scientists have created a bandage that is actually able to clot a bullet wound in less than a minute. The bandages are laced with a mixture of ground shrimp shells and vinegar, a concoction that has been found to clot blood instantly. The key ingredient in the shrimp shells is called chitosan."
  • A Critical look on ChitosanA critical look on the claims how chitosan can be used for weight management

Footnotes

  1. Kean T, Roth S, Thanou M (2005). "Trimethylated chitosans as non-viral gene delivery vectors: cytotoxicity and transfection efficiency". J Control Release. 103 (3): 643–53. PMID 15820411. |access-date= requires |url= (help)
  2. "Chitosan; Poly-D-glucosamine (128930) Fact Sheet". US Environmental Protection Agency. 2006. Retrieved 2006-07-10. Unknown parameter |month= ignored (help)
  3. Alan Woodmansey (Highway Engineer) (2002). "Chitosan Treatment of Sediment Laden Water - Washington State I-90 Issaquah Project". Federal Highway Administration. U.S. Department of Transportation. Retrieved 2006-07-10. Unknown parameter |month= ignored (help)
  4. Rayner, Terry. "Fining and Clarifying Agents". Retrieved 2006-07-18.
  5. "HemCon Medical Technologies Inc". 2004.
  6. Pusateri, A. E., S. J. McCarthy, K. W. Gregory, R. A. Harris, L. Cardenas, A. T. McManus & C. W. Goodwin Jr. (2003). "Effect of a chitosan-based hemostatic dressing on blood loss and survival in a model of severe venous hemorrhage and hepatic injury in swine". Journal of Trauma. 4 (1): 177–182. Unknown parameter |quotes= ignored (help)
  7. Karen Lurie. "War Bandages".
  8. Kevin McCue (2003). "New Bandage Uses Biopolymer". chemistry.org. American Chemical Society. Retrieved 2006-07-10. Unknown parameter |month= ignored (help)

cs:Chitosan da:Chitosan de:Chitosan nl:Chitosan fi:Kitosaani


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