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T RENPYPOLS : A New Water‐Soluble Iron Chelator (both Fe III and Fe II ) Involving Six‐Membered Coordination Rings
Author(s) -
Baret Paul,
Béguin Claude,
Gellon Gisèle,
Pierre JeanLouis,
Serratrice Guy,
Thomas Fabrice,
Laulhère JeanPierre,
SaintAman Eric
Publication year - 2000
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(200006)2000:6<1219::aid-ejic1219>3.0.co;2-r
Subject(s) - chemistry , chelation , coordination complex , water soluble , stereochemistry , combinatorial chemistry , polymer chemistry , inorganic chemistry , organic chemistry , metal
An eight‐step synthesis of a new water‐soluble tripodal ligand TRENPYPOLS (tris[2‐(2‐hydroxy‐3‐(2‐pyridinyl)‐5‐sulfobenzamido)ethyl]amine) is described. TRENPYPOLS is built by connecting the TREN spacer through a tris‐amide moiety to the ortho phenolic position of three 2‐(2‐hydroxyphenyl)pyridine chelating subunits, (followed by the sulfonation of the 5‐positions). The three [O,N pyr ] bidentate subunits of TRENPYPOLS involve six‐membered coordination rings. The solution coordination chemistry of the ligand and its iron complexes have been studied by means of pH potentiometric, spectrophotometric and voltammetric methods. The stability constants, log β 110 , are 30.1 for the ferric complex and 17.7 for the ferrous complex (pFe III and pFe II values are 23.6 and 11.2 respectively at pH = 7.4, [L] tot = 10 −5 M , [Fe] tot = 10 −6 M ). Comparison with the data of o‐trensox (8‐hydroxyquinoline subunits with a 5‐membered chelate ring) corroborates the usual rules concerning the influence of the chelate ring size on complexation ability. Fe III ‐ TRENPYPOLS has been tested as a single source of iron in nutritional experiments with Arabidopsis thaliana plant cells. The efficiency towards growth and resistance to iron chlorosis is good, comparable to that of Fe III ‐EDTA, the most commonly used complex for in vitro cell cultures.