Glutaraldehyde

Glutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional crosslinker and fixative.{{cite journal |doi=10.1016/S0002-9440(10)64472-0|title=Effect of Fixatives and Tissue Processing on the Content and Integrity of Nucleic Acids |year=2002 |last1=Srinivasan |first1=Mythily |last2=Sedmak |first2=Daniel |last3=Jewell |first3=Scott |journal=The American Journal of Pathology |volume=161 |issue=6 |pages=1961–1971 |pmid=12466110 |pmc=1850907 }}{{cite journal |doi=10.1016/j.carbpol.2014.07.007|title=Application of chitosan and its derivatives as adsorbents for dye removal from water and wastewater: A review |year=2014 |last1=Vakili |first1=Mohammadtaghi |last2=Rafatullah |first2=Mohd |last3=Salamatinia |first3=Babak |last4=Abdullah |first4=Ahmad Zuhairi |last5=Ibrahim |first5=Mahamad Hakimi |last6=Tan |first6=Kok Bing |last7=Gholami |first7=Zahra |last8=Amouzgar |first8=Parisa |journal=Carbohydrate Polymers |volume=113 |pages=115–130 |pmid=25256466 }} It kills cells quickly by crosslinking their proteins. It is usually employed alone or mixed with formaldehydeKarnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A as the first of two fixative processes to stabilize specimens such as bacteria, plant material, and human cells. A second fixative procedure uses osmium tetroxide to crosslink and stabilize cell and organelle membrane lipids.

Another application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to generate toxoid vaccines, e.g., the pertussis (whooping cough) toxoid component in Tdap vaccines.

In material science glutaraldehyde application areas range from polymers to metals and biomaterials. Glutaraldehyde is commonly used as fixing agent before characterization of biomaterials for microscopy. Glutaraldehyde is a powerful crosslinking agent for many polymers containing primary amine groups.{{Citation |last=Al-Muhanna |first=Muhanna K. |title=Chapter 1 - Synthesis of tailor-made polysaccharides: An overview |date=2023-01-01 |work=Tailor-Made Polysaccharides in Drug Delivery |pages=1–27 |editor-last=Nayak |editor-first=Amit Kumar |url=https://www.sciencedirect.com/science/article/pii/B9780128212868000136 |access-date=2024-06-03 |publisher=Academic Press |doi=10.1016/b978-0-12-821286-8.00013-6 |isbn=978-0-12-821286-8 |last2=Anwar |first2=Naushad |last3=Hasnain |first3=Md Saquib |last4=Nayak |first4=Amit Kumar |editor2-last=Hasnain |editor2-first=Md Saquib}}{{Citation |last=Kozlovskaya |first=V. |title=1.25 Polymer Films Using LbL Self-Assembly |date=2017 |work=Comprehensive Biomaterials II |pages=554–569 |url=https://doi.org/10.1016/B978-0-08-100691-7.00177-4 |access-date=2024-06-03 |publisher=Elsevier |doi=10.1016/b978-0-08-100691-7.00177-4 |isbn=978-0-08-100692-4 |last2=Kharlampieva |first2=E. |last3=Sukhishvili |first3=S.A.}} Glutaraldehdye also can be used for an interlinking agent to improve the adhesion force between two polymeric coatings.{{Citation| last1 = Erisen| first1 = Deniz. E| title = A novel chitosan and polydopamine interlinked bioactive coating for metallic biomaterials| journal = Journal of Materials Science: Materials in Medicine| volume = 33| issue = 10| pages = 65| publisher = Springer-Nature| date = 23 September 2022| issn = 1573-4838| doi = 10.1007/s10856-022-06688-x| pmid = 36138240| pmc = 9499904}} Glutaraldehyde is also used to protect against corrosion of undersea pipes.{{Cite conference |last=Falck |first=Christian |last2=Kleppe |first2=Terje |last3=Maribu |first3=Jarleiv |date=1993-12-23 |title=Commissioning of long subsea pipelines - environmental aspects |url=https://inis.iaea.org/collection/NCLCollectionStore/_Public/29/045/29045754.pdf |journal= |publication-place=Norway |publication-date=1997-12-31 |osti=593571}}

Glutaraldehyde is used as a disinfectant and medication.{{cite book|last1=Bonewit-West|first1=Kathy|title=Clinical Procedures for Medical Assistants|date=2015|publisher=Elsevier Health Sciences|isbn=9781455776610|page=96|url=https://books.google.com/books?id=pTwcBgAAQBAJ&pg=PA96|language=en|url-status=live|archive-url=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=pTwcBgAAQBAJ&pg=PA96|archive-date=23 September 2017}} Usually applied as a solution, it is used to sterilize surgical instruments and other areas.

As a medication it is used to treat plantar warts. For this purpose, a 10% w/v solution is used. It dries the skin, facilitating physical removal of the wart.[http://www.nhs.uk/medicine-guides/pages/MedicineOverview.aspx?medicine=Glutarol NHS Choices: Glutarol] {{webarchive|url=https://web.archive.org/web/20150205153347/http://www.nhs.uk/medicine-guides/pages/MedicineOverview.aspx?medicine=Glutarol |date=5 February 2015 }}

Glutaraldehyde is also used in the treatment of hyperhidrosis under the control of dermatologists in people who have frequent sweating but do not respond to aluminum chloride. Glutaraldehyde solution is an effective agent to treat palmar and plantar hyperhidrosis as an alternative to tannic acid and formaldehyde.{{Citation| last1 = Juhlin| first1 = L | last2 = Hansson| first2 = H| title = Topical glutaraldehyde for plantar hyperhidrosis | journal = Archives of Dermatology| volume = 97| issue = 3| pages = 327–330| publisher = American Medical Association | date = 1968| url = https://jamanetwork.com/journals/jamadermatology/article-abstract/530562 | issn = 0003-987X| doi = 10.1001/archderm.1968.01610090099017| pmid = 5641337 }}

Glutaraldehyde diluted with water is often marketed as alternative to carbon dioxide gas injection for aquarium plants, but it lacks any characteristics that promote the growth of aquatic plants, and does not raise the {{CO2}} concentration of water it is added to {{Citation needed|date=September 2024}}. Aquarists also commonly use it in low concentrations as an algicide.{{cite web | last=Antiquis | first=Avus | title=Glutaraldehyde Revisited | website=praquatics.com - Aquarium Forums By Hobbyists For Hobbyists | date=20 September 2017 | url=https://praquatics.com/forums/threads/glutaraldehyde-revisited.2566/ | access-date=10 October 2022 | archive-date=14 February 2022 | archive-url=https://web.archive.org/web/20220214181745/https://praquatics.com/forums/threads/glutaraldehyde-revisited.2566/ | url-status=live }}

Side effects include skin irritation. If exposed to large amounts, nausea, headache, and shortness of breath may occur. Protective equipment is recommended when used, especially in high concentrations. Glutaraldehyde is effective against a range of microorganisms including spores. Glutaraldehyde is a dialdehyde.{{cite book |last1=Pfafflin |first1=James R. |last2=Ziegler |first2=Edward N. |title=Encyclopedia of Environmental Science and Engineering: A-L |date=2006 |publisher=CRC Press |isbn=9780849398438 |page=235 |url=https://books.google.com/books?id=ylktfmkJQZwC&pg=PA235 |language=en |access-date=19 September 2020 |archive-date=10 October 2022 |archive-url=https://web.archive.org/web/20221010053021/https://books.google.com/books?id=ylktfmkJQZwC&pg=PA235 |url-status=live }} It works by a number of mechanisms.{{cite book|last1=Fraise|first1=Adam P.|last2=Maillard|first2=Jean-Yves|last3=Sattar|first3=Syed|title=Russell, Hugo and Ayliffe's Principles and Practice of Disinfection, Preservation and Sterilization|date=2012|publisher=John Wiley & Sons|isbn=9781118425862|page=Chapter 2|url=https://books.google.com/books?id=b6Pz6kMw3akC&pg=PT50|language=en|url-status=live|archive-url=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=b6Pz6kMw3akC&pg=PT50|archive-date=23 September 2017}}

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[http://www.ccohs.ca/oshanswers/diseases/asthma.html Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma] {{webarchive|url=https://web.archive.org/web/20090427164024/http://www.ccohs.ca/oshanswers/diseases/asthma.html |date=27 April 2009 }} Document last updated on 8 February 2005 There is no strong evidence of carcinogenic activity,[http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr490.pdf Toxicology and Carcinogenesis Studies of Glutaraldehyde] {{webarchive|url=https://web.archive.org/web/20121010200602/http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr490.pdf |date=10 October 2012 }} However, some occupations that work with this chemical have an increased risk of some cancers.

Glutaraldehyde is produced industrially by the catalytic oxidation of cyclopentene by hydrogen peroxide, which can be achieved in the presence of various tungstic acid-based heteropoly acid catalysts.{{cite journal |last1=Chandler |first1=Malcolm |title=Hydrogen Peroxide-Tungstic Acid |journal=Encyclopedia of Reagents for Organic Synthesis |date=15 April 2001 |pages=rh046 |doi=10.1002/047084289X.rh046|isbn=0471936235 }}{{cite journal |last1=Furukawa |first1=Hiroshi |last2=Nakamura |first2=Teiji |last3=Inagaki |first3=Hiroyuki |last4=Nishikawa |first4=Eiichiro |last5=Imai |first5=Chihiro |last6=Misono |first6=Makoto |date=5 May 1988 |title=Oxidation of Cyclopentene with Hydrogen Peroxide Catalyzed by 12-Heteropoly Acids |url=https://www.journal.csj.jp/doi/pdf/10.1246/cl.1988.877 |journal=Chemistry Letters |volume=17 |issue=5 |pages=877–880 |doi=10.1246/cl.1988.877}} This reaction essentially mimics ozonolysis. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.{{Ullmann |author1=Christian Kohlpaintner |author2=Markus Schulte |author3=Jürgen Falbe |author4=Peter Lappe |author5=Jürgen Weber|title=Aldehydes, Aliphatic|year=2008|doi= 10.1002/14356007.a01_321.pub2}}

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Like other dialdehydes, (e.g., glyoxal) and simple aldehydes (e.g., formaldehyde), glutaraldehyde hydrates in aqueous solution, forming gem-diols. These diols in turn equilibrate with cyclic hemiacetal.{{cite journal |author1=Whipple Earl B. |author2=Ruta Michael |year=1974 |title=Structure of Aqueous Glutaraldehyde |journal=J. Org. Chem. |volume=39 |issue= 12|pages=1666–1668 |doi=10.1021/jo00925a015}} Monomeric glutaraldehyde polymerizes by aldol condensation and Michael reactions yielding alpha, beta-unsaturated poly-glutaraldehyde and related oligomers. This reaction occurs at alkaline pH values.{{cite journal |last1=Migneault |first1=Isabelle |last2=Dartiguenave |first2=Catherine |last3=Bertrand |first3=Michel J. |last4=Waldron |first4=Karen C. |year=2004 |title=Glutaraldehyde: Behavior in aqueous solution, reaction with proteins, and application to enzyme crosslinking |url= |journal=BioTechniques |volume=37 |issue=5 |pages=790–802 |doi=10.2144/04375RV01 |pmid=15560135 |doi-access=free}}

:File:GlutaldehydeHydrateEquilibria.png

A number of mechanisms have been invoked to explain the biocidal and fixative properties of glutaraldehyde. Like many other aldehydes, it reacts with primary amines and thiol groups, which are common functional groups in proteins, nucleic acids and polymeric materials. Being bi-functional, glutaraldehyde is a crosslinker, which rigidifies macromolecular structures and shuts down their reactivity.{{Ullmann |author1=H. Uhr |author2=B. Mielke |author3=O. Exner |author4=K. R. Payne |author5=E. Hill |title=Biocides |year=2013 |doi=10.1002/14356007.a16_563.pub2}}

File:Imine-synthesis.svg

The aldehyde groups in glutaraldehyde are susceptible to formation of imines by reaction with the amines of lysine and nucleic acids. The derivatives from aldol condensation of pairs of glutaraldehyde also undergo imine formation.

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{{reflist}}

• [https://www.dcceew.gov.au/environment/protection/npi/substances/fact-sheets/glutaraldehyde-sources-emissions Glutaraldehyde: Sources of emissions] AU National Pollutant Inventory
• [https://www.cdc.gov/niosh/topics/glutaraldehyde/ Glutaraldehyde] US National Institute for Occupational Safety and Health
• [https://webbook.nist.gov/cgi/cbook.cgi?Name=glutaraldehyde&Units=SI Glutaraldehyde] NIST Standard Reference Data

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