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Pentetic acid or diethylenetriaminepentaacetic acid ( DTPA) is an aminopolycarboxylic acid consisting of a diethylenetriamine backbone with five carboxymethyl groups. The molecule can be viewed as an expanded version of EDTA and is used similarly. It is a white solid with limited solubility in water.


Coordination properties
The of DTPA has a high affinity for metal . Thus, the penta-anion DTPA5− is potentially an assuming that each nitrogen centre and each –COO group counts as a centre for coordination. The formation constants for its complexes are about 100 greater than those for EDTA.J. Roger Hart "Ethylenediaminetetraacetic Acid and Related Chelating Agents" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. As a , DTPA wraps around a metal ion by forming up to eight bonds. Its complexes can also have an extra water molecule that coordinates the metal ion. Transition metals, however, usually form less than eight . So, after forming a complex with a metal, DTPA still has the ability to bind to other reagents, as is shown by its derivative . For example, in its complex with copper(II), DTPA binds in a hexadentate manner utilizing the three amine centres and three of the five carboxylates.V. V. Fomenko, T. N. Polynova, M. A. Porai-Koshits, G. L. Varlamova and N. I. Pechurova Crystal structure of copper (II) diethylenetriaminepentaacetate monohydrate Journal of Structural Chemistry, 1973, Vol. 14, 529.

The distinction between H5DTPA, "DTPA", and DTPA5− is often not explicit.


Chelating applications
Like the more common EDTA, DTPA is predominantly used as agent for complexing and sequestering metal ions.

DTPA has been considered for treatment of radioactive materials such as , , and other . In theory, these complexes are more apt to be eliminated in . It is normally administered as the or salt (Ca or Zn-DTPA), since these ions are readily displaced by more highly charged cations and mainly to avoid to depleting them in the organism. DTPA forms complexes with (IV), (IV), (IV), and (III/IV).(2) Brown, M. A.; Paulenova, A.; Gelis, A. V. "Aqueous Complexation of Thorium(IV), Uranium(IV), Neptunium(IV), Plutonium(III/IV), and Cerium(III/IV) with DTPA" Inorganic Chemistry 2012, volume 51, 7741-7748.

In August, 2004 the U.S. US Food and Drug Administration (USFDA) determined zinc-DTPA and calcium-DTPA to be safe and effective for treatment of those who have breathed in or otherwise been contaminated internally by plutonium, americium, or curium. The recommended treatment is for an initial dose of calcium-DTPA, as this salt of DTPA has been shown to be more effective in the first 24 hours after internal contamination by plutonium, americium, or curium. After that time has elapsed both calcium-DTPA and zinc-DTPA are similarly effective in reducing internal contamination with , or , and zinc-DTPA is less likely to deplete the body's normal levels of zinc and other metals essential to health. Each drug can be administered by for those who have breathed in contamination, and by intravenous injection for those contaminated by other routes.

(Gd3+)-DTPA compounds are MRI .Caravan, Peter; Ellison, Jeffrey J.; McMurry, Thomas J. ; Lauffer, Randall B. "Gadolinium(III) Chelates as MRI Contrast Agents:  Structure, Dynamics, and Applications" Chem. Revs. 1999, volume 99, pp. 2293–2342.

DTPA under the form of iron(II) chelate (Fe-DTPA, 10 – 11 wt. %) is also used as . The more soluble form of iron, Fe(II), is a needed by . By binding to Fe2+ ions DTPA prevents their precipitation as Fe(OH)3, or Fe2O3 · n H2O poorly soluble oxy-hydroxides after their by dissolved . It increases the of Fe2+ and Fe3+ ions in water, and therefore the of iron for aquatic plants. It contributes so to maintain iron under a dissolved form (probably a mix of Fe(II) and Fe(III) DTPA complexes) in the . It is unclear to what extent does DTPA really contribute to protect dissolved Fe2+ against air oxidation and if the Fe(III)-DTPA complex cannot also be directly assimilated by aquatic plants simply because of its enhanced solubility. Under natural conditions, i.e., in the absence of complexing DTPA, Fe2+ is more easily assimilated by most organisms, because of its 100-fold higher solubility than that of Fe3+.

In DTPA is also used to remove dissolved ferrous and ferric ions (and other redox-active metal ions, such as or ) that otherwise would accelerate the decomposition of hydrogen peroxide (H2O2 reduction by Fe2+ ions according to the Fenton reaction mechanism). This helps preserving the capacity of the hydrogen peroxide stock which is used as to bleach pulp in the chlorine-free process of paper making.Colodette, J. L. (1987). Factors affecting hydrogen peroxide stability in the brightening of mechanical and chemi-mechanical pulps (Doctoral dissertation, State University of New York College of Environmental Science and Forestry). Several thousands tons of DTPA are produced annually for this purpose in order to limit the non-negligible losses of H2O2 by this mechanism.

DTPA chelating properties are also useful in deactivating and ions in hair products. DTPA is used in over 150 cosmetic products.Burnett, L. C. "Final Report on the Safety Assessment of Pentasodium Pentetate and Pentetic Acid as Used in Cosmetics" International Journal of Toxicology 2008, 27, 71-92.


Biochemistry
DTPA is more effective than to deactivate redox-active metal ions such as Fe(II)/(III), Mn(II)/(IV) and Cu(I)/(II) perpetuating induced in cells by and hydrogen peroxide. DTPA is also used in involving redox-active metal ions.


Environmental impact
An unexpected negative environmental impact of chelating agents, as DTPA, is their toxicity for the in the treatment of effluents. Most of the DTPA worldwide production (several thousands of tons) is intended to avoid hydrogen peroxide decomposition by redox-active and ions in the chlorine-free Kraft pulping processes (total chlorine free (TCF) and environmental chlorine free (ECF) processes). DTPA decreases the biological oxygen demand (BOD) of activated sludges and therefore their microbial activity.


Related compounds
Compounds that are structurally related to DTPA are used in medicine, taking advantage of the high affinity of the triaminopentacarboxylate scaffold for metal ions.
  • In ibritumomab tiuxetan, the chelator tiuxetan is a modified version of DTPA whose carbon backbone contains an isothiocyanatobenzyl and a .
  • In capromab pendetide and satumomab pendetide, the chelator (GYK-DTPA) is a modified DTPA containing a linker used to connect the chelate to an .
  • Pentetreotide is a modified DTPA attached to a segment.
  • DTPA and derivatives are used to chelate to form an MRI contrast agent, such as Magnevist.
  • Technetium-99m is chelated with DTPA for ventilation perfusion (V/Q) scans and radioisotope renography scans.
    (2013). 9781118691083, John Wiley & Sons. .


See also
  • Radiopharmaceutical
  • Hydrogen peroxide decomposition
  • DTPA in chlorine-free Kraft pulping

This article incorporates material from Facts about DTPA, a produced by the United States Centers for Disease Control and Prevention.

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