1024:(EDTA) proved too stable and not nutritionally viable. If the mineral was taken from the EDTA ligand, the ligand could not be used by the body and would be expelled. During the expulsion process, the EDTA ligand randomly chelated and stripped other minerals from the body. According to the Association of American Feed Control Officials (AAFCO), a metal–amino acid chelate is defined as the product resulting from the reaction of metal ions from a soluble metal salt with amino acids, with a
1410:
2596:
1345:), is declining (−6% annually), because of the persisting concerns over their toxicity and negative environmental impact. In 2013, these greener alternative chelants represented approximately 15% of the total aminopolycarboxylic acids demand. This is expected to rise to around 21% by 2018, replacing and aminophosphonic acids used in cleaning applications. Examples of some Greener alternative chelating agents include
153:
139:
608:
is lost when the chelate complex is formed with bidentate ligand than when the complex with monodentate ligands is formed. This is one of the factors contributing to the entropy difference. Other factors include solvation changes and ring formation. Some experimental data to illustrate the effect are
845:
These data confirm that the enthalpy changes are approximately equal for the two reactions and that the main reason for the greater stability of the chelate complex is the entropy term, which is much less unfavorable. In general it is difficult to account precisely for thermodynamic values in terms
1319:
Metal chelate compounds are common components of fertilizers to provide micronutrients. These micronutrients (manganese, iron, zinc, copper) are required for the health of the plants. Most fertilizers contain phosphate salts that, in the absence of chelating agents, typically convert these metal
2165:
Vosjan MJ, Perk LR, Visser GW, Budde M, Jurek P, Kiefer GE, van Dongen GA (April 2010). "Conjugation and radiolabeling of monoclonal antibodies with zirconium-89 for PET imaging using the bifunctional chelate p-isothiocyanatobenzyl-desferrioxamine".
1336:
chelators are the most widely consumed chelating agents; however, the percentage of the greener alternative chelators in this category continues to grow. The consumption of traditional aminopolycarboxylates chelators, in particular the EDTA
492:
1033:. Since the early development of these compounds, much more research has been conducted, and has been applied to human nutrition products in a similar manner to the animal nutrition experiments that pioneered the technology.
1028:
in the range of 1–3 (preferably 2) moles of amino acids for one mole of metal. The average weight of the hydrolyzed amino acids must be approximately 150 and the resulting molecular weight of the chelate must not exceed
2541:
Kołodyńska D (2011) Chelating agents of a new generation as an alternative to conventional chelators for heavy metal ions removal from different waste waters. In
Expanding Issues in Desalination pp. 339-370.
793:
721:
1048:
adhesives were first designed and produced in the 1950s based on a co-monomer chelate with calcium on the surface of the tooth and generated very weak water-resistant chemical bonding (2–3 MPa).
653:
581:
543:
401:
344:
of methylamine is twice that of ethylenediamine and the concentration of copper is the same in both reactions, the concentration is much higher than the concentration because
1383:
Dechelation (or de-chelation) is a reverse process of the chelation in which the chelating agent is recovered by acidifying solution with a mineral acid to form a precipitate.
1307:. Although the treatment is often referred to as "softening", chelation has little effect on the water's mineral content, other than to make it soluble and lower the water's
592:
Since the enthalpy should be approximately the same for the two reactions, the difference between the two stability constants is due to the effects of entropy. In equation (
2252:
Parac-Vogt, Tatjana N.; Kimpe, Kristof; Laurent, Sophie; Vander Elst, Luce; Burtea, Carmen; Chen, Feng; Muller, Robert N.; Ni, Yicheng; Verbruggen, Alfons (2005-05-06).
1087:". Although beneficial in cases of serious lead poisoning, use of disodium EDTA (edetate disodium) instead of calcium disodium EDTA has resulted in fatalities due to
897:
are also typical chelators. In addition to these adventitious chelators, several biomolecules are specifically produced to bind certain metals (see next section).
2254:"Synthesis, characterization, and pharmacokinetic evaluation of a potential MRI contrast agent containing two paramagnetic centers with albumin binding affinity"
2630:
2550:
Kolodynska D (2013) Application of a new generation of complexing agents inremoval of heavy metal ions from different wastes. Env Sci Pollut Res 20: 5939-5949.
176:
The chelate effect is the greater affinity of chelating ligands for a metal ion than that of similar nonchelating (monodentate) ligands for the same metal.
411:
2081:
Caravan P, Ellison JJ, McMurry TJ, Lauffer RB (September 1999). "Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and
Applications".
900:
Virtually all metalloenzymes feature metals that are chelated, usually to peptides or cofactors and prosthetic groups. Such chelating agents include the
2922:
99:
or other crustaceans, is suggested for the caliperlike groups which function as two associating units and fasten to the central atom so as to produce
2055:
2733:
3087:
3058:
1975:
1909:
1713:
1507:
1550:
Krämer U, Cotter-Howells JD, Charnock JM, Baker AJ, Smith JA (1996). "Free histidine as a metal chelator in plants that accumulate nickel".
60:
and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually
586:
262:
methylamine ligands of approximately the same donor power, indicating that the Cu–N bonds are approximately the same in the two reactions.
87:
was first applied in 1920 by Sir
Gilbert T. Morgan and H. D. K. Drew, who stated: "The adjective chelate, derived from the great claw or
1332:
Because of their wide needs, the overall chelating agents growth was 4% annually during 2009–2014 and the trend is likely to increase.
328:
Electrical charges have been omitted for simplicity of notation. The square brackets indicate concentration, and the subscripts to the
2498:
967:
from minerals and rocks. Most metal complexes in the environment and in nature are bound in some form of chelate ring (e.g., with a
2623:
2059:
1076:
727:
1071:. Chelating agents convert these metal ions into a chemically and biochemically inert form that can be excreted. Chelation using
2824:
1730:
Das S, Miller DR, Kaufman Y, Martinez
Rodriguez NR, Pallaoro A, Harrington MJ, Gylys M, Israelachvili JN, Waite JH (March 2015).
661:
329:
1091:. Disodium EDTA is not approved by the FDA for any use, and all FDA-approved chelation therapy products require a prescription.
3136:
3007:
1338:
1264:
1021:
846:
of changes in solution at the molecular level, but it is clear that the chelate effect is predominantly an effect of entropy.
3141:
2915:
1346:
244:) the ethylenediamine forms a chelate complex with the copper ion. Chelation results in the formation of a five-membered CuC
881:, and polynucleic acids are excellent polydentate ligands for many metal ions. Organic compounds such as the amino acids
2882:
2786:
948:
residues in mussel foot protein-1 to improve the strength of the threads that they use to secure themselves to surfaces.
2616:
605:
3104:
2532:
Dixon NJ (2012) Greener chelating agents, In
Handbook of green chemistry: Designing safer chemicals. Wiley 9: 281-307.
2695:
2802:
1354:
1203:
Chelation in the intestinal tract is a cause of numerous interactions between drugs and metal ions (also known as "
266:
3131:
2908:
2710:
2678:
1167:, and the gadolinium complexes often employ the usage of octadentate ligands such as DTPA, according to Desreux
2851:
2846:
2807:
1333:
341:
179:
The thermodynamic principles underpinning the chelate effect are illustrated by the contrasting affinities of
1940:
1462:"CLXII.—Researches on residual affinity and co-ordination. Part II. Acetylacetones of selenium and tellurium"
3092:
3063:
1358:
2870:
2760:
2209:
Price, Eric W.; Orvig, Chris (2014-01-07). "Matching chelators to radiometals for radiopharmaceuticals".
1303:
are also well-known chelating agents. Chelators are used in water treatment programs and specifically in
628:
556:
518:
376:
2863:
2858:
2836:
2781:
2688:
2668:
2026:"Deaths associated with hypocalcemia from chelation therapy--Texas, Pennsylvania, and Oregon, 2003–2005"
1499:
1342:
1148:
1072:
35:
2900:
1304:
1160:
1652:
Ha SB, Smith AP, Howden R, Dietrich WM, Bugg S, O'Connell MJ, Goldsbrough PB, Cobbett CS (June 1999).
2745:
2728:
2639:
1792:
1606:
1559:
1252:
1219:
1084:
850:
270:
157:
119:
273:
for the reaction: the larger the equilibrium constant, the higher the concentration of the complex.
2841:
2819:
2705:
2663:
1188:
2438:
Lomaestro BM, Bailie GR (May 1995). "Absorption interactions with fluoroquinolones. 1995 update".
2829:
2720:
2653:
2463:
2191:
1575:
1414:
1156:
48:
and their molecules to metal ions. It involves the formation or presence of two or more separate
30:
This article is about sequestering agents in general. For chemicals used in food processing, see
912:. Many microbial species produce water-soluble pigments that serve as chelating agents, termed
923:
2935:
2875:
2755:
2683:
2673:
2573:
2494:
2455:
2420:
2371:
2322:
2281:
2273:
2234:
2226:
2183:
2147:
2098:
2037:
1981:
1971:
1905:
1867:
1818:
1761:
1709:
1683:
1634:
1503:
1350:
1060:
1056:
1004:
604:) there are three particles on the left and one on the right. This difference means that less
107:
2814:
2700:
2486:
2447:
2410:
2402:
2361:
2353:
2312:
2265:
2218:
2175:
2137:
2129:
2090:
1857:
1849:
1808:
1800:
1751:
1743:
1673:
1665:
1624:
1614:
1567:
1532:
1491:
1473:
1242:
936:
61:
1267:
and asymmetric isomerization. The latter has the practical use of manufacture of synthetic
3073:
2776:
1418:
1409:
1378:
1284:
1204:
1104:
1034:
184:
169:
142:
123:
111:
49:
2025:
1886:
1796:
1610:
1563:
3098:
2887:
2415:
2406:
2390:
2366:
2341:
2142:
2117:
1862:
1837:
1813:
1780:
1756:
1731:
1654:"Phytochelatin synthase genes from Arabidopsis and the yeast Schizosaccharomyces pombe"
1629:
1594:
1080:
996:
878:
92:
72:
2595:
2002:
1678:
1653:
3125:
3068:
3032:
2956:
2740:
2451:
1446:
1366:
1238:
1180:
1037:
is an example of one of these compounds that has been developed for human nutrition.
1030:
988:
894:
882:
487:{\displaystyle \Delta G^{\ominus }=-RT\ln K=\Delta H^{\ominus }-T\Delta S^{\ominus }}
337:
2317:
2300:
2253:
2984:
2939:
2467:
2195:
1579:
1215:
1088:
992:
931:
913:
866:
502:
368:
100:
2561:
2490:
1838:"Peptide Length and Dopa Determine Iron-Mediated Cohesion of Mussel Foot Proteins"
1836:
Das S, Martinez
Rodriguez NR, Wei W, Waite JH, Israelachvili JN (September 2015).
106:
Chelation is useful in applications such as providing nutritional supplements, in
598:) there are two particles on the left and one on the right, whereas in equation (
3048:
3012:
3002:
2979:
2974:
2600:
2481:
Hart JR (2011). "Ethylenediaminetetraacetic Acid and
Related Chelating Agents".
1781:"Iron-clad fibers: a metal-based biological strategy for hard flexible coatings"
1362:
1300:
1280:
1152:
1000:
918:
909:
188:
161:
31:
1599:
Proceedings of the
National Academy of Sciences of the United States of America
2750:
2357:
2133:
1324:
is the typical chelating agent that keeps these metal ions in a soluble form.
1211:
1208:
1192:
1100:
1025:
968:
964:
952:
927:
905:
127:
79:, meaning "claw"; the ligands lie around the central atom like the claws of a
2577:
2277:
2230:
1985:
1536:
1119:
chelate complexes have also been explored. Bifunctional chelate complexes of
1804:
1779:
Harrington MJ, Masic A, Holten-Andersen N, Waite JH, Fratzl P (April 2010).
1619:
1320:
ions into insoluble solids that are of no nutritional value to the plants.
1292:
1260:
1231:
1172:
1120:
1116:
901:
886:
259:
53:
2375:
2285:
2269:
2238:
2187:
2151:
2102:
2041:
1871:
1853:
1822:
1765:
1687:
1638:
1523:
Schwarzenbach G (1952). "Der
Chelateffekt" [The Chelation Effect].
1279:
A chelating agent is the main component of some rust removal formulations.
2459:
2424:
2326:
2179:
1669:
3024:
1477:
1128:
548:
2518:(2013) IHS Chemical, Chemical Insight and Forecasting: Chelating Agents.
1433:
971:
or a protein). Thus, metal chelates are relevant to the mobilization of
2222:
1268:
1227:
1140:
1136:
1124:
1064:
956:
874:
152:
17:
2608:
2094:
1747:
1732:"Tough coating proteins: subtle sequence variation modulates cohesion"
2948:
1966:
Anusavice KJ (2012-09-27). "Chapter 12: Bonding and
Bonding Agents".
1571:
1255:
are often chelated complexes. A representative example is the use of
1246:
1184:
1144:
1132:
1045:
984:
980:
972:
945:
941:
890:
870:
510:
180:
145:
57:
1595:"Aluminum tolerance genes are conserved between monocots and dicots"
1461:
1249:, allowing for some increase in clarity of vision for the patient.
3053:
1944:
1256:
960:
151:
137:
2994:
2966:
1392:
1321:
1296:
1288:
1223:
1176:
1112:
1068:
976:
138:
96:
80:
45:
2904:
2612:
2118:"Manganese-based MRI contrast agents: past, present and future"
1108:
115:
788:{\displaystyle -T\Delta S^{\ominus }\mathrm {/kJ\ mol^{-1}} }
2116:
Pan D, Schmieder AH, Wickline SA, Lanza GM (November 2011).
2024:
Centers for Disease Control Prevention (CDC) (March 2006).
1308:
716:{\displaystyle \Delta H^{\ominus }\mathrm {/kJ\ mol^{-1}} }
2056:"Questions and Answers on Unapproved Chelation Products"
1179:, is used in the treatment of rheumatoid arthritis, and
269:
approach to describing the chelate effect considers the
2391:"Iron supplements: a common cause of drug interactions"
1237:
EDTA, which binds to calcium, is used to alleviate the
940:, is the strongest chelating agent known. The marine
730:
664:
631:
559:
521:
414:
379:
1970:(12th ed.). Elsevier Health. pp. 257–268.
1927:
The Roles of Amino Acid Chelates in Animal Nutrition
1397:
Pages displaying wikidata descriptions as a fallback
1155:. These chelate complexes often employ the usage of
3041:
3023:
2993:
2965:
2947:
2795:
2769:
2719:
2646:
1902:
Metals in the Environment: Analysis by Biodiversity
2342:"Current use of chelation in American health care"
787:
715:
647:
575:
537:
486:
395:
955:is attributed to organic chelating agents (e.g.,
944:use metal chelation esp. Fe chelation with the
2483:Ullmann's Encyclopedia of Industrial Chemistry
1195:, as well as refractory rheumatoid arthritis.
869:exhibit the ability to dissolve certain metal
2916:
2624:
2566:Annales Universitatis Mariae Curie-Sklodowska
1887:"Introduction to the Lithosphere: Weathering"
1708:. Mill Valley, CA: University Science Books.
1466:Journal of the Chemical Society, Transactions
8:
2562:"EDTA – synthesis and selected applications"
1245:. The calcium may then be removed from the
2030:MMWR. Morbidity and Mortality Weekly Report
853:, are discussed in Greenwood and Earnshaw (
126:to assist in the removal of metals, and in
2923:
2909:
2901:
2631:
2617:
2609:
1997:
1995:
1943:. Albion Laboratories, Inc. Archived from
1889:. University of British Columbia Okanagan.
1417: by Kaana Asemave available under the
258:) the bidentate ligand is replaced by two
2414:
2365:
2316:
2299:Kean WF, Hart L, Buchanan WW (May 1997).
2141:
1861:
1812:
1755:
1699:
1697:
1677:
1628:
1618:
775:
751:
750:
744:
729:
703:
679:
678:
672:
663:
639:
630:
567:
558:
529:
520:
478:
459:
422:
413:
387:
378:
110:to remove toxic metals from the body, as
2395:British Journal of Clinical Pharmacology
611:
27:Type of chemical bonding with metal ions
2389:Campbell NR, Hasinoff BB (March 1991).
1426:
2003:"FDA Issues Chelation Therapy Warning"
849:Other explanations, including that of
2528:
2526:
2524:
2514:
2512:
2510:
1968:Phillips' Science of Dental Materials
979:, the uptake and the accumulation of
7:
1706:Principles of Bioinorganic Chemistry
301:
275:
213:
193:
1369:, amino acids, plant extracts etc.
1183:, which forms chelate complexes of
1083:. It is not approved for treating "
648:{\displaystyle \Delta G^{\ominus }}
576:{\displaystyle \Delta S^{\ominus }}
538:{\displaystyle \Delta H^{\ominus }}
396:{\displaystyle \Delta G^{\ominus }}
148:chelating to a metal with two bonds
2407:10.1111/j.1365-2125.1991.tb05525.x
1147:are often used for conjugation to
772:
768:
765:
759:
756:
737:
700:
696:
693:
687:
684:
665:
632:
560:
522:
471:
452:
415:
380:
25:
1295:. A common synthetic chelator is
1199:Nutritional advantages and issues
1077:U.S. Food and Drug Administration
2594:
2452:10.2165/00002018-199512050-00004
1413: This article incorporates
1408:
1059:is an antidote for poisoning by
2305:British Journal of Rheumatology
1929:. Westwood: Noyes Publications.
1904:. New York, NY: Marcel Dekker.
1347:ethylenediamine disuccinic acid
1339:ethylenediaminetetraacetic acid
1265:Noyori asymmetric hydrogenation
1022:ethylenediaminetetraacetic acid
64:, but this is not a necessity.
1434:IUPAC definition of chelation.
1207:" in nutrition). As examples,
1187:, is used in the treatment of
609:shown in the following table.
1:
2599:The dictionary definition of
2491:10.1002/14356007.a10_095.pub2
2346:Journal of Medical Toxicology
2318:10.1093/rheumatology/36.5.560
2258:Chemistry: A European Journal
1842:Advanced Functional Materials
1450:, from Greek, denotes a claw.
367:, is related to the standard
1704:Lippard SJ, Berg JM (1994).
1275:Cleaning and water softening
34:. For the isopod genus, see
2560:Ryczkowski, Janusz (2019).
1460:Morgan GT, Drew HD (1920).
1079:(FDA) for serious cases of
1020:Synthetic chelates such as
951:In earth science, chemical
916:. For example, species of
893:, and polypeptides such as
600:
594:
551:change of the reaction and
254:
240:
3158:
1941:"Albion Ferrochel Website"
1593:Magalhaes JV (June 2006).
1376:
1355:methylglycinediacetic acid
1222:families are chelators of
1163:(DFO), according to Meijs
1151:for use in antibody-based
889:, organic diacids such as
29:
3082:
2711:Thermodynamic equilibrium
2358:10.1007/s13181-013-0347-2
2134:10.1016/j.tet.2011.07.076
1496:Chemistry of the Elements
1395: – chemical compound
1334:Aminopolycarboxylic acids
1075:has been approved by the
991:. Selective chelation of
363:An equilibrium constant,
340:of the complex. When the
118:, in manufacturing using
2864:Distribution coefficient
2808:Hammett acidity function
2787:Liquid–liquid extraction
2696:Le Chatelier's principle
2340:Wax PM (December 2013).
2211:Chemical Society Reviews
1537:10.1002/hlca.19520350721
1241:that often results from
342:analytical concentration
44:is a type of bonding of
1805:10.1126/science.1181044
1620:10.1073/pnas.0603957103
1175:, a chelate complex of
3137:Coordination chemistry
2825:Coordination complexes
2761:Thermodynamic activity
2270:10.1002/chem.200401207
1854:10.1002/adfm.201502256
1525:Helvetica Chimica Acta
1359:glutamic diacetic acid
789:
717:
649:
577:
539:
509:is the temperature in
488:
397:
173:
149:
3142:Equilibrium chemistry
2837:Dissociation constant
2782:Equilibrium unfolding
2669:Equilibrium chemistry
2180:10.1038/nprot.2010.13
1670:10.1105/tpc.11.6.1153
1500:Butterworth-Heinemann
1494:, Earnshaw A (1997).
1343:nitrilotriacetic acid
1253:Homogeneous catalysts
1149:monoclonal antibodies
1099:Chelate complexes of
1073:calcium disodium EDTA
1035:Ferrous bis-glycinate
1016:Animal feed additives
922:are known to secrete
790:
718:
650:
578:
540:
489:
398:
155:
141:
120:homogeneous catalysts
36:Chelator (crustacean)
2746:Predominance diagram
2729:Equilibrium constant
2005:. September 26, 2008
1947:on September 3, 2011
1478:10.1039/ct9201701456
1085:heavy metal toxicity
728:
662:
629:
557:
519:
412:
377:
271:equilibrium constant
2820:Binding selectivity
2796:Specific equilibria
2706:Reversible reaction
2664:Dynamic equilibrium
2640:Chemical equilibria
1925:Ashmead HD (1993).
1797:2010Sci...328..216H
1611:2006PNAS..103.9749M
1564:1996Natur.379..635K
1157:hexadentate ligands
606:entropy of disorder
330:stability constants
3109:Never to phase III
2830:Macrocyclic effect
2654:Chemical stability
2223:10.1039/c3cs60304k
2062:. February 2, 2016
1328:Economic situation
1103:are often used as
999:(e.g., removal of
785:
713:
645:
573:
535:
484:
393:
174:
160:with nonchelating
150:
56:(multiple bonded)
3119:
3118:
2936:chelation therapy
2898:
2897:
2876:Common-ion effect
2803:Acid dissociation
2756:Reaction quotient
2674:Equilibrium stage
2264:(10): 3077–3086.
2128:(44): 8431–8444.
2095:10.1021/cr980440x
1977:978-1-4377-2418-9
1911:978-0-8247-0523-7
1900:Prasad M (2001).
1848:(36): 5840–5847.
1748:10.1021/bm501893y
1736:Biomacromolecules
1715:978-0-935702-73-6
1509:978-0-08-037941-8
1351:polyaspartic acid
1305:steam engineering
1161:desferrioxamine B
1057:Chelation therapy
1052:Chelation therapy
1005:radioactive waste
843:
842:
827:Cu + en ⇌ Cu(en)
764:
692:
369:Gibbs free energy
326:
325:
300:
299:
236:
235:
212:
211:
108:chelation therapy
62:organic compounds
16:(Redirected from
3149:
3132:Chelating agents
2932:Chelating agents
2925:
2918:
2911:
2902:
2815:Binding constant
2701:Phase separation
2633:
2626:
2619:
2610:
2598:
2582:
2581:
2557:
2551:
2548:
2542:
2539:
2533:
2530:
2519:
2516:
2505:
2504:
2478:
2472:
2471:
2435:
2429:
2428:
2418:
2386:
2380:
2379:
2369:
2337:
2331:
2330:
2320:
2296:
2290:
2289:
2249:
2243:
2242:
2206:
2200:
2199:
2168:Nature Protocols
2162:
2156:
2155:
2145:
2113:
2107:
2106:
2083:Chemical Reviews
2078:
2072:
2071:
2069:
2067:
2052:
2046:
2045:
2021:
2015:
2014:
2012:
2010:
1999:
1990:
1989:
1963:
1957:
1956:
1954:
1952:
1937:
1931:
1930:
1922:
1916:
1915:
1897:
1891:
1890:
1882:
1876:
1875:
1865:
1833:
1827:
1826:
1816:
1791:(5975): 216–20.
1776:
1770:
1769:
1759:
1727:
1721:
1719:
1701:
1692:
1691:
1681:
1649:
1643:
1642:
1632:
1622:
1590:
1584:
1583:
1572:10.1038/379635a0
1547:
1541:
1540:
1520:
1514:
1513:
1498:(2nd ed.).
1488:
1482:
1481:
1457:
1451:
1442:
1436:
1431:
1412:
1398:
1243:band keratopathy
1189:Wilson's disease
930:that bind iron.
794:
792:
791:
786:
784:
783:
782:
762:
755:
749:
748:
722:
720:
719:
714:
712:
711:
710:
690:
683:
677:
676:
656:
654:
652:
651:
646:
644:
643:
612:
585:is the standard
584:
582:
580:
579:
574:
572:
571:
547:is the standard
546:
544:
542:
541:
536:
534:
533:
493:
491:
490:
485:
483:
482:
464:
463:
427:
426:
404:
402:
400:
399:
394:
392:
391:
359:
320:
302:
294:
276:
230:
214:
206:
194:
71:is derived from
50:coordinate bonds
21:
3157:
3156:
3152:
3151:
3150:
3148:
3147:
3146:
3122:
3121:
3120:
3115:
3114:
3099:Clinical trials
3078:
3037:
3019:
2989:
2961:
2943:
2929:
2899:
2894:
2847:Self-ionization
2791:
2777:Buffer solution
2765:
2715:
2642:
2637:
2591:
2586:
2585:
2559:
2558:
2554:
2549:
2545:
2540:
2536:
2531:
2522:
2517:
2508:
2501:
2480:
2479:
2475:
2437:
2436:
2432:
2388:
2387:
2383:
2339:
2338:
2334:
2298:
2297:
2293:
2251:
2250:
2246:
2208:
2207:
2203:
2164:
2163:
2159:
2115:
2114:
2110:
2089:(9): 2293–352.
2080:
2079:
2075:
2065:
2063:
2054:
2053:
2049:
2023:
2022:
2018:
2008:
2006:
2001:
2000:
1993:
1978:
1965:
1964:
1960:
1950:
1948:
1939:
1938:
1934:
1924:
1923:
1919:
1912:
1899:
1898:
1894:
1884:
1883:
1879:
1835:
1834:
1830:
1778:
1777:
1773:
1729:
1728:
1724:
1716:
1703:
1702:
1695:
1651:
1650:
1646:
1605:(26): 9749–50.
1592:
1591:
1587:
1558:(6566): 635–8.
1549:
1548:
1544:
1522:
1521:
1517:
1510:
1502:. p. 910.
1490:
1489:
1485:
1459:
1458:
1454:
1443:
1439:
1432:
1428:
1405:
1396:
1389:
1381:
1379:Transmetalation
1375:
1330:
1317:
1277:
1201:
1105:contrast agents
1097:
1095:Contrast agents
1054:
1043:
1018:
1013:
995:is relevant to
963:) that extract
879:polysaccharides
863:
810:
806:
802:
771:
740:
726:
725:
699:
668:
660:
659:
635:
627:
626:
624:
563:
555:
554:
552:
525:
517:
516:
514:
474:
455:
418:
410:
409:
383:
375:
374:
372:
358:
351:
345:
336:, indicate the
318:
311:
292:
285:
251:
247:
228:
220:
204:
185:ethylenediamine
172:(right) ligands
170:ethylenediamine
143:Ethylenediamine
136:
124:water treatment
112:contrast agents
39:
28:
23:
22:
15:
12:
11:
5:
3155:
3153:
3145:
3144:
3139:
3134:
3124:
3123:
3117:
3116:
3113:
3112:
3111:
3110:
3107:
3096:
3090:
3084:
3083:
3080:
3079:
3077:
3076:
3071:
3066:
3061:
3056:
3051:
3045:
3043:
3039:
3038:
3036:
3035:
3029:
3027:
3021:
3020:
3018:
3017:
3016:
3015:
3005:
2999:
2997:
2991:
2990:
2988:
2987:
2982:
2977:
2971:
2969:
2963:
2962:
2960:
2959:
2953:
2951:
2945:
2944:
2930:
2928:
2927:
2920:
2913:
2905:
2896:
2895:
2893:
2892:
2891:
2890:
2880:
2879:
2878:
2868:
2867:
2866:
2856:
2855:
2854:
2844:
2839:
2834:
2833:
2832:
2822:
2817:
2812:
2811:
2810:
2799:
2797:
2793:
2792:
2790:
2789:
2784:
2779:
2773:
2771:
2767:
2766:
2764:
2763:
2758:
2753:
2748:
2743:
2738:
2737:
2736:
2725:
2723:
2717:
2716:
2714:
2713:
2708:
2703:
2698:
2693:
2692:
2691:
2686:
2676:
2671:
2666:
2661:
2656:
2650:
2648:
2644:
2643:
2638:
2636:
2635:
2628:
2621:
2613:
2607:
2606:
2590:
2589:External links
2587:
2584:
2583:
2552:
2543:
2534:
2520:
2506:
2500:978-3527306732
2499:
2473:
2430:
2381:
2352:(4): 303–307.
2332:
2291:
2244:
2217:(1): 260–290.
2201:
2157:
2108:
2073:
2047:
2016:
1991:
1976:
1958:
1932:
1917:
1910:
1892:
1877:
1828:
1771:
1722:
1714:
1693:
1664:(6): 1153–64.
1658:The Plant Cell
1644:
1585:
1542:
1531:(7): 2344–59.
1515:
1508:
1483:
1452:
1437:
1425:
1424:
1404:
1401:
1400:
1399:
1388:
1385:
1374:
1371:
1329:
1326:
1316:
1313:
1276:
1273:
1200:
1197:
1096:
1093:
1081:lead poisoning
1053:
1050:
1042:
1039:
1017:
1014:
1012:
1009:
997:bioremediation
989:microorganisms
934:, produced by
862:
859:
841:
840:
837:
834:
831:
828:
824:
823:
820:
817:
814:
811:
808:
804:
800:
796:
795:
781:
778:
774:
770:
767:
761:
758:
754:
747:
743:
739:
736:
733:
723:
709:
706:
702:
698:
695:
689:
686:
682:
675:
671:
667:
657:
642:
638:
634:
622:
616:
570:
566:
562:
532:
528:
524:
495:
494:
481:
477:
473:
470:
467:
462:
458:
454:
451:
448:
445:
442:
439:
436:
433:
430:
425:
421:
417:
390:
386:
382:
356:
349:
324:
323:
314:
312:
309:
298:
297:
288:
286:
283:
249:
245:
234:
233:
224:
222:
218:
210:
209:
200:
198:
135:
134:Chelate effect
132:
122:, in chemical
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3154:
3143:
3140:
3138:
3135:
3133:
3130:
3129:
3127:
3108:
3106:
3103:
3102:
3100:
3097:
3094:
3091:
3089:
3086:
3085:
3081:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3046:
3044:
3040:
3034:
3033:Prussian blue
3031:
3030:
3028:
3026:
3022:
3014:
3011:
3010:
3009:
3006:
3004:
3001:
3000:
2998:
2996:
2992:
2986:
2983:
2981:
2978:
2976:
2973:
2972:
2970:
2968:
2964:
2958:
2957:Penicillamine
2955:
2954:
2952:
2950:
2946:
2941:
2937:
2933:
2926:
2921:
2919:
2914:
2912:
2907:
2906:
2903:
2889:
2886:
2885:
2884:
2881:
2877:
2874:
2873:
2872:
2869:
2865:
2862:
2861:
2860:
2857:
2853:
2850:
2849:
2848:
2845:
2843:
2840:
2838:
2835:
2831:
2828:
2827:
2826:
2823:
2821:
2818:
2816:
2813:
2809:
2806:
2805:
2804:
2801:
2800:
2798:
2794:
2788:
2785:
2783:
2780:
2778:
2775:
2774:
2772:
2768:
2762:
2759:
2757:
2754:
2752:
2749:
2747:
2744:
2742:
2741:Phase diagram
2739:
2735:
2734:determination
2732:
2731:
2730:
2727:
2726:
2724:
2722:
2718:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2690:
2687:
2685:
2682:
2681:
2680:
2677:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2651:
2649:
2645:
2641:
2634:
2629:
2627:
2622:
2620:
2615:
2614:
2611:
2605:at Wiktionary
2604:
2603:
2597:
2593:
2592:
2588:
2579:
2575:
2571:
2567:
2563:
2556:
2553:
2547:
2544:
2538:
2535:
2529:
2527:
2525:
2521:
2515:
2513:
2511:
2507:
2502:
2496:
2492:
2488:
2484:
2477:
2474:
2469:
2465:
2461:
2457:
2453:
2449:
2446:(5): 314–33.
2445:
2441:
2434:
2431:
2426:
2422:
2417:
2412:
2408:
2404:
2400:
2396:
2392:
2385:
2382:
2377:
2373:
2368:
2363:
2359:
2355:
2351:
2347:
2343:
2336:
2333:
2328:
2324:
2319:
2314:
2311:(5): 560–72.
2310:
2306:
2302:
2295:
2292:
2287:
2283:
2279:
2275:
2271:
2267:
2263:
2259:
2255:
2248:
2245:
2240:
2236:
2232:
2228:
2224:
2220:
2216:
2212:
2205:
2202:
2197:
2193:
2189:
2185:
2181:
2177:
2174:(4): 739–43.
2173:
2169:
2161:
2158:
2153:
2149:
2144:
2139:
2135:
2131:
2127:
2123:
2119:
2112:
2109:
2104:
2100:
2096:
2092:
2088:
2084:
2077:
2074:
2061:
2057:
2051:
2048:
2043:
2039:
2035:
2031:
2027:
2020:
2017:
2004:
1998:
1996:
1992:
1987:
1983:
1979:
1973:
1969:
1962:
1959:
1946:
1942:
1936:
1933:
1928:
1921:
1918:
1913:
1907:
1903:
1896:
1893:
1888:
1881:
1878:
1873:
1869:
1864:
1859:
1855:
1851:
1847:
1843:
1839:
1832:
1829:
1824:
1820:
1815:
1810:
1806:
1802:
1798:
1794:
1790:
1786:
1782:
1775:
1772:
1767:
1763:
1758:
1753:
1749:
1745:
1742:(3): 1002–8.
1741:
1737:
1733:
1726:
1723:
1717:
1711:
1707:
1700:
1698:
1694:
1689:
1685:
1680:
1675:
1671:
1667:
1663:
1659:
1655:
1648:
1645:
1640:
1636:
1631:
1626:
1621:
1616:
1612:
1608:
1604:
1600:
1596:
1589:
1586:
1581:
1577:
1573:
1569:
1565:
1561:
1557:
1553:
1546:
1543:
1538:
1534:
1530:
1527:(in German).
1526:
1519:
1516:
1511:
1505:
1501:
1497:
1493:
1487:
1484:
1479:
1475:
1471:
1467:
1463:
1456:
1453:
1449:
1448:
1441:
1438:
1435:
1430:
1427:
1423:
1422:
1420:
1416:
1411:
1402:
1394:
1391:
1390:
1386:
1384:
1380:
1372:
1370:
1368:
1367:gluconic acid
1364:
1360:
1356:
1352:
1348:
1344:
1340:
1335:
1327:
1325:
1323:
1314:
1312:
1310:
1306:
1302:
1298:
1294:
1290:
1286:
1282:
1274:
1272:
1270:
1266:
1262:
1259:(a bidentate
1258:
1254:
1250:
1248:
1244:
1240:
1239:hypercalcemia
1235:
1233:
1229:
1225:
1221:
1217:
1213:
1210:
1206:
1198:
1196:
1194:
1190:
1186:
1182:
1181:penicillamine
1178:
1174:
1170:
1166:
1162:
1158:
1154:
1150:
1146:
1142:
1138:
1134:
1130:
1126:
1122:
1118:
1115:particle and
1114:
1110:
1106:
1102:
1094:
1092:
1090:
1086:
1082:
1078:
1074:
1070:
1066:
1062:
1058:
1051:
1049:
1047:
1040:
1038:
1036:
1032:
1027:
1023:
1015:
1010:
1008:
1006:
1002:
998:
994:
990:
986:
982:
978:
974:
970:
966:
962:
958:
954:
949:
947:
943:
939:
938:
933:
929:
925:
921:
920:
915:
911:
907:
903:
898:
896:
895:phytochelatin
892:
888:
884:
883:glutamic acid
880:
876:
872:
868:
860:
858:
856:
852:
851:Schwarzenbach
847:
838:
835:
832:
829:
826:
825:
821:
818:
815:
812:
798:
797:
779:
776:
752:
745:
741:
734:
731:
724:
707:
704:
680:
673:
669:
658:
640:
636:
623:
621:
617:
614:
613:
610:
607:
603:
602:
597:
596:
590:
588:
568:
564:
550:
530:
526:
512:
508:
504:
500:
479:
475:
468:
465:
460:
456:
449:
446:
443:
440:
437:
434:
431:
428:
423:
419:
408:
407:
406:
388:
384:
370:
366:
361:
355:
348:
343:
339:
338:stoichiometry
335:
331:
322:
315:
313:
308:
304:
303:
296:
289:
287:
282:
278:
277:
274:
272:
268:
267:thermodynamic
263:
261:
257:
256:
243:
242:
232:
225:
223:
216:
215:
208:
201:
199:
196:
195:
192:
190:
186:
182:
177:
171:
167:
163:
159:
154:
147:
144:
140:
133:
131:
129:
125:
121:
117:
113:
109:
104:
102:
98:
94:
90:
86:
82:
78:
74:
70:
65:
63:
59:
55:
51:
47:
43:
37:
33:
19:
2985:Deferoxamine
2931:
2883:Vapor–liquid
2770:Applications
2658:
2601:
2569:
2565:
2555:
2546:
2537:
2482:
2476:
2443:
2439:
2433:
2401:(3): 251–5.
2398:
2394:
2384:
2349:
2345:
2335:
2308:
2304:
2294:
2261:
2257:
2247:
2214:
2210:
2204:
2171:
2167:
2160:
2125:
2121:
2111:
2086:
2082:
2076:
2064:. Retrieved
2050:
2036:(8): 204–7.
2033:
2029:
2019:
2007:. Retrieved
1967:
1961:
1949:. Retrieved
1945:the original
1935:
1926:
1920:
1901:
1895:
1885:Pidwirny M.
1880:
1845:
1841:
1831:
1788:
1784:
1774:
1739:
1735:
1725:
1705:
1661:
1657:
1647:
1602:
1598:
1588:
1555:
1551:
1545:
1528:
1524:
1518:
1495:
1492:Greenwood NN
1486:
1469:
1465:
1455:
1445:
1440:
1429:
1407:
1406:
1382:
1331:
1318:
1301:Phosphonates
1291:and laundry
1285:soften water
1278:
1251:
1236:
1216:tetracycline
1202:
1168:
1164:
1098:
1089:hypocalcemia
1055:
1044:
1019:
1011:Applications
993:heavy metals
950:
935:
932:Enterobactin
917:
914:siderophores
899:
867:biomolecules
864:
854:
848:
844:
619:
599:
593:
591:
506:
503:gas constant
498:
496:
364:
362:
353:
346:
333:
327:
316:
306:
290:
280:
264:
253:
239:
237:
226:
202:
178:
175:
165:
116:MRI scanning
105:
101:heterocyclic
88:
84:
76:
68:
66:
41:
40:
3095:from market
3013:Dexrazoxane
2980:Deferiprone
2975:Deferasirox
2888:Henry's law
2679:Free energy
2440:Drug Safety
2301:"Auranofin"
2122:Tetrahedron
1472:: 1456–65.
1341:) and NTA (
1315:Fertilizers
1283:is used to
1281:Citric acid
1269:(–)-menthol
1153:PET imaging
1111:, although
919:Pseudomonas
910:chlorophyll
799:Cu + 2 MeNH
615:Equilibrium
260:monodentate
217:Cu + 2 MeNH
189:methylamine
162:methylamine
128:fertilizers
83:. The term
54:polydentate
32:sequestrant
3126:Categories
2871:Solubility
2842:Hydrolysis
2751:Phase rule
1403:References
1377:See also:
1361:(L-GLDA),
1293:detergents
1209:antibiotic
1193:cystinuria
1101:gadolinium
1041:Dental use
1026:mole ratio
969:humic acid
965:metal ions
953:weathering
928:pyoverdine
906:hemoglobin
252:ring. In (
197:Cu + en ⇌
168:chelating
52:between a
3105:Phase III
3093:Withdrawn
2942:, others)
2859:Partition
2689:Helmholtz
2659:Chelation
2578:2083-358X
2278:0947-6539
2231:1460-4744
1986:785080357
1419:CC BY 4.0
1261:phosphine
1220:quinolone
1173:Auranofin
1121:zirconium
1117:manganese
1109:MRI scans
1029:800
924:pyochelin
904:rings in
902:porphyrin
887:histidine
865:Numerous
861:In nature
803:⇌ Cu(MeNH
777:−
746:⊖
738:Δ
732:−
705:−
674:⊖
666:Δ
641:⊖
633:Δ
569:⊖
561:Δ
531:⊖
523:Δ
480:⊖
472:Δ
466:−
461:⊖
453:Δ
444:
432:−
424:⊖
416:Δ
389:⊖
381:Δ
187:(en) vs.
183:(II) for
158:complexes
95:) of the
69:chelation
67:The word
42:Chelation
3025:Thallium
2852:of water
2647:Concepts
2376:24113860
2286:15776492
2239:24173525
2188:20360768
2152:22043109
2103:11749483
2042:16511441
1951:July 12,
1872:28670243
1823:20203014
1766:25692318
1688:10368185
1639:16785425
1421:license.
1387:See also
1373:Reversal
1357:(MGDA),
1353:(PASA),
1349:(EDDS),
1205:minerals
1159:such as
1129:fluorine
957:peptides
875:proteins
873:. Thus,
589:change.
549:enthalpy
103:rings."
2602:chelate
2468:2006138
2460:7669261
2425:2054263
2416:1368348
2367:3846961
2327:9189058
2196:5087493
2143:3203535
2066:May 14,
2009:May 14,
1863:5488267
1814:3087814
1793:Bibcode
1785:Science
1757:4514026
1630:1502523
1607:Bibcode
1580:4318712
1560:Bibcode
1363:citrate
1311:level.
1214:of the
1141:bromine
1137:yttrium
1125:gallium
1065:arsenic
1061:mercury
975:in the
942:mussels
937:E. coli
871:cations
855:loc.cit
655:
625:
587:entropy
583:
553:
545:
515:
511:kelvins
501:is the
403:
373:
164:(left)
85:chelate
18:Chelate
3088:WHO-EM
2949:Copper
2721:Models
2576:
2497:
2466:
2458:
2423:
2413:
2374:
2364:
2325:
2284:
2276:
2237:
2229:
2194:
2186:
2150:
2140:
2101:
2040:
1984:
1974:
1908:
1870:
1860:
1821:
1811:
1764:
1754:
1712:
1686:
1679:144235
1676:
1637:
1627:
1578:
1552:Nature
1506:
1444:Latin
1247:cornea
1234:ions.
1230:, and
1185:copper
1165:et al.
1145:iodine
1133:copper
1067:, and
1046:Dentin
985:plants
981:metals
973:metals
961:sugars
891:malate
839:−4.19
836:−56.48
833:−60.67
763:
691:
497:where
181:copper
146:ligand
75:χηλή,
58:ligand
3054:BAPTA
3042:Other
2940:V03AC
2684:Gibbs
2464:S2CID
2192:S2CID
1576:S2CID
1447:chela
1289:soaps
1263:) in
1257:BINAP
1212:drugs
1169:et al
1143:, or
1003:from
983:into
830:10.62
822:19.9
819:−57.3
816:−37.4
93:Greek
89:chele
77:chēlē
73:Greek
3074:EGTA
3069:DTPA
3064:DMSA
3059:DMPS
3008:EDTA
2995:Lead
2967:Iron
2574:ISSN
2495:ISBN
2456:PMID
2421:PMID
2372:PMID
2323:PMID
2282:PMID
2274:ISSN
2235:PMID
2227:ISSN
2184:PMID
2148:PMID
2099:PMID
2068:2016
2038:PMID
2011:2016
1982:OCLC
1972:ISBN
1953:2011
1906:ISBN
1868:PMID
1819:PMID
1762:PMID
1710:ISBN
1684:PMID
1635:PMID
1504:ISBN
1415:text
1393:EDDS
1322:EDTA
1297:EDTA
1218:and
1191:and
1177:gold
1113:iron
1069:lead
987:and
977:soil
959:and
946:Dopa
926:and
908:and
885:and
813:6.55
618:log
505:and
265:The
238:In (
97:crab
81:crab
46:ions
3049:ALA
3003:BAL
2487:doi
2448:doi
2411:PMC
2403:doi
2362:PMC
2354:doi
2313:doi
2266:doi
2219:doi
2176:doi
2138:PMC
2130:doi
2091:doi
2060:FDA
1858:PMC
1850:doi
1809:PMC
1801:doi
1789:328
1752:PMC
1744:doi
1674:PMC
1666:doi
1625:PMC
1615:doi
1603:103
1568:doi
1556:379
1533:doi
1474:doi
1470:117
1287:in
1107:in
1007:).
857:).
405:by
166:and
156:Cu
114:in
3128::
3101::
2934:/
2572:.
2570:74
2568:.
2564:.
2523:^
2509:^
2493:.
2485:.
2462:.
2454:.
2444:12
2442:.
2419:.
2409:.
2399:31
2397:.
2393:.
2370:.
2360:.
2348:.
2344:.
2321:.
2309:36
2307:.
2303:.
2280:.
2272:.
2262:11
2260:.
2256:.
2233:.
2225:.
2215:43
2213:.
2190:.
2182:.
2170:.
2146:.
2136:.
2126:67
2124:.
2120:.
2097:.
2087:99
2085:.
2058:.
2034:55
2032:.
2028:.
1994:^
1980:.
1866:.
1856:.
1846:25
1844:.
1840:.
1817:.
1807:.
1799:.
1787:.
1783:.
1760:.
1750:.
1740:16
1738:.
1734:.
1696:^
1682:.
1672:.
1662:11
1660:.
1656:.
1633:.
1623:.
1613:.
1601:.
1597:.
1574:.
1566:.
1554:.
1529:35
1468:.
1464:.
1365:,
1309:pH
1299:.
1271:.
1232:Mg
1228:Ca
1226:,
1224:Fe
1171:.
1139:,
1135:,
1131:,
1127:,
1123:,
1063:,
1031:Da
1001:Cs
877:,
513:.
441:ln
371:,
360:.
357:12
352:≫
350:11
332:,
310:12
305:=
284:11
279:=
221:⇌
191:.
130:.
2938:(
2924:e
2917:t
2910:v
2632:e
2625:t
2618:v
2580:.
2503:.
2489::
2470:.
2450::
2427:.
2405::
2378:.
2356::
2350:9
2329:.
2315::
2288:.
2268::
2241:.
2221::
2198:.
2178::
2172:5
2154:.
2132::
2105:.
2093::
2070:.
2044:.
2013:.
1988:.
1955:.
1914:.
1874:.
1852::
1825:.
1803::
1795::
1768:.
1746::
1720:.
1718:.
1690:.
1668::
1641:.
1617::
1609::
1582:.
1570::
1562::
1539:.
1535::
1512:.
1480:.
1476::
1337:(
809:2
807:)
805:2
801:2
780:1
773:l
769:o
766:m
760:J
757:k
753:/
742:S
735:T
708:1
701:l
697:o
694:m
688:J
685:k
681:/
670:H
637:G
620:β
601:2
595:1
565:S
527:H
507:T
499:R
476:S
469:T
457:H
450:=
447:K
438:T
435:R
429:=
420:G
385:G
365:K
354:β
347:β
334:β
321:)
319:4
317:(
307:β
295:)
293:3
291:(
281:β
255:2
250:2
248:N
246:2
241:1
231:)
229:2
227:(
219:2
207:)
205:1
203:(
91:(
38:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
