Phosphonates and phosphonic acids are organophosphorus compounds containing C-PO(OH)2 or C-PO(OR)2 groups (where R = alkyl, aryl). Phosphonic acids, typically handled as salts, are usually nonvolatile solids which are poorly soluble in organic solvents, but soluble in water and common alcohols. Many commercially important compounds are phosphonates, including glyphosate, the herbicide "Roundup", and ethephon, a commonly used plant growth regulator. Bisphosphonates are popular drugs for management of osteoporosis. |
Clodronic acid is really a bisphosphonate used being a drug to deal with osteoporosis.
In biology and medicinal chemistry, phosphonate groups are utilized as stable bioisoteres for phosphate, like within the antiviral nucleotide analogue, Tenofovir, among the cornerstones of anti-HIV therapy.
Occurrence by nature
Glyphosate, the herbicide "Roundup", is really a phosphonate.
2-aminoethylphosphonic acid: the very first identified natural phosphonate.
Phosphonates are among the three causes of phosphate intake in biological cells. Another two are inorganic phosphate and organophosphates.
The naturally sourced phosphonate 2-aminoethylphosphonic acid was initially identified in 1959 in plants and several animals, where it really is localized in membranes. Phosphonates are very common among different organisms, from prokaryotes to eubacteria and fungi, mollusks, insects as well as others. These were first reported in natural soils by Newman and Tate (1980). The biological role from the natural phosphonates continues to be poorly understood. Bis- or polyphosphonates have not been found to happen naturally.
Several natural product phosphonate substances with antibiotic properties have already been identified. Phosphonate natural product antibiotics include fosfomycin that is FDA-approved for the management of non-complicated urinary tract infection in addition to several pre-clinically investigated substances like Fosmidomycin (inhibitor isoprenyl synthase), SF-2312 (inhibitor from the glycolytic enzyme Enolase, and substances of unknown mode of actions like Alahopcin. Although phosphonates are profoundly cell impermeable, natural product phosphonate antibiotics work well against several organisms, because many bacterial species express Glycerol-3-phosphate and Glucose-6-phosphate importers, which may be hijaked by phosphonate antibiotics. Fosfomycin resistant bacterial strains frequently have mutations that inactivate these transporters; however, such mutations usually are not maintained in the lack of antibiotic due to the fitness cost they impose.
Because the work of Schwarzenbach in 1949, phosphonic acids are referred to as effective chelating agents. The development of an amine group in to the molecule to acquire -NH2-C-PO(OH)2 raises the metal binding abilities from the phosphonate. Examples for such compounds are NTMP, EDTMP and DTPMP. These phosphonates would be the structural analogues towards the popular aminopolycarboxylate like EDTA. The steadiness from the metal complexes increases with increasing quantity of phosphonic acid groups. Phosphonates are highly water-soluble as the phosphonic acids are just sparingly so.
Phosphonates work well chelating agents. Which is, they bind tightly to di- and trivalent metal ions, that is beneficial in water softening. In this manner, they prevent formation of insoluble precipitates (scale). The binding of those ligands also suppresses the catalytic properties of metal ions. They may be stable under harsh conditions. Therefore, an essential industrial usage of phosphonates is within cooling waters, desalination systems, as well as in oil fields to inhibit scale formation. Phosphonates can also be regularly utilized in reverse osmosis systems as anti-scalants. Phosphonates in cooling water systems also help to control corrosion of iron and steel. In pulp and paper manufacturing as well as in textile industry they function as "peroxide bleach stabilizers", by chelating metals that may inactivate the peroxide. In detergents they are utilized as a mix of chelating agent, scale inhibitor, and bleach stabilizer. Phosphonates can also be increasingly utilized in medicine to deal with disorders related to bone formation and calcium metabolism. Furthermore, they function as carriers for radionuclides in bone cancer treatments (see samarium-153-ethylene diamine tetramethylene phosphonate).
In medicine, phosphonates and bisphosphonates are generally used as inhibitors of enzymes which utilize phosphates and diphosphates as substrates. Most notably, these enzymes include the ones that make the intermediates of cholesterol biosynthesis.
Phosphonate nucleotide analogue, like Tenofovir, Cidofovir and Adefovir are critical antiviral medications, which in a variety of pro-drug forms, can be used for the management of HIV, Hepatitis B as well as others.
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