A New hydroxypyrone powerful chelator: from synthesis to AlIII, FeIII, CuII and ZnII complex formation equilibria, and structural characterization

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The Acta of the International Symposia on Metal Complexes (ISSN: 2239-2459) are published annually online by the ISMEC Group.

Editors:

Begoña García (President of the Scientific Committee of ISMEC 2013)

Departamento de Química Facultad de Ciencias Universidad de Burgos Plaza de Missael Bañuelos s/n 09001 Burgos (Spain)

begar@ubu.es

Guido Crisponi (President of the ISMEC Group)

Dipartimento di Scienze Chimiche Università degli Studi di Cagliari Cittadella Universitaria

09042 Monserrato – Cagliari, ITALY

crisponi@unica.it

Scientific Committee of ISMEC 2013:

Begoña García (University of Burgos, Spain) Guido Crisponi (University of Cagliari, Italy) Antonio Bianchi (University of Florence, Italy) Etelka Farkas (University of Debrecen, Hungary) Enrique García-España (University of Valencia, Spain) Carlos C.F. Geraldes (University of Coimbra, Portugal) Juan Niclós (University of Granada, Spain) Henryk Kozlowski (University of Wroclaw, Poland) José M. Leal (University of Burgos, Spain)

Fernando Pina (University of Nova Lisbon, Portugal) Maria C. Rangel (University of Oporto, Portugal) Silvio Sammartano (University of Messina, Italy)

M. Amélia Santos (University of Técnica Lisbon, Portugal) Fernando Secco (University of Pisa, Italy)

Manuel Valiente (University of Autónoma Barcelona, Spain) Maurizio Remelli (University of Ferrara, Italy)

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Acta of the International Symposia on Metal Complexes – ISMEC Acta, Volume 3

ISMEC 2013, June 16th – 20th 2013 – Burgos (Spain)

OC-6 52

A new hydroxypyrone powerful chelator.

From synthesis to Al

III

, Fe

III

, Cu

II

and Zn

II

complex formation equilibria,

and structural characterization.

Leonardo TOSO,a) Guido CRISPONI,a) Maria Amelia SANTOS, b) Sergio M. MARQUES, b) Valeria M. NURCHI, a) Joanna I. LACHOWICZ,a) Miriam CRESPO-ALONSO,a) Delara MANSOORI,a,c) Alicia DOMINGUEZ-MARTIN,c) Juan

NICLOS-GUTIERREZ,c) Duane CHOQUESILLO-LAZARTE,c,d) Maria Antonietta ZORODDU,e) Massimiliano PEANA e)

a)

Department of Chemical and Geological Sciences, University of Cagliari, Cittadella Universitaria, 09042 Monserrato, Cagliari, Italy; crisponi@unica.it

b)

Centro Quimica Estrutural, Instituto Superior Tecnico, Universidade Técnica de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal

c)

Department of Inorganic Chemistry, Faculty of Pharmacy, Campus Cartuja, University of Granada, E-18071, Granada, Spain

d)

Laboratorio de Estudios Cristalográficos, IACT, CSIC-Universidad de Granada, Av. de las Palmeras 4, E-18100 Armilla, Granada, Spain

e)

Department of Chemistry and Pharmacy, University of Sassari, Via Vienna 2, 07100 Sassari, Italy

In the frame of our research interest on kojic acid derivatives as powerful chelators for the trivalent iron and aluminium cations [1-4], we have designed, synthesized, and characterized the new ligand 6,6'-(((2-(diethylamino)ethyl)azanediyl)bis(methylene))bis(5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one), L9.

In this communication will be present the study on protonation constants and on the complex formation equilibria with iron and aluminium and with the bivalent essential metal ions, zinc and copper.

O N OH O HO N O O OH OH

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References: [1] [2] [3] [4] References: [1] [2] [3] [4] X References: Nurchi A.; Szewczuk

to design kojic acid derivatives with new perspectives 104, Nurchi V Niclós Lis Dalton Trans. Toso L.; Marques S.M.; Niclos Choquesillo

synthesized as iron che

Toso L.; Crisponi G.; Nurchi V.M.; Crespo M.A.; Marques S.M.; Niclos

Choquesillo

family of hydroxypyrone ligands.

X-ray structures of

References:

Nurchi A.; Niclós Szewczuk

to design kojic acid derivatives with new perspectives 104, Nurchi V Niclós Lis T., Dalton Trans. Toso L.; Marques S.M.; Niclos Choquesillo

Choquesillo

ray structures of

References:

Nurchi Niclós Szewczuk

to design kojic acid derivatives with new perspectives 560 Nurchi V Niclós-T., Dalton Trans. Toso L.; Marques S.M.; Niclos Choquesillo

Choquesillo

ray structures of

V.M. Niclós Szewczuk

to design kojic acid derivatives with new perspectives 560–569

Nurchi V.M.; Lachowicz J.I. -Gutiérrez

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III).

Dalton Trans.

Toso L.; Crisponi G.; Nurchi V.M.; Crespo Marques S.M.; Niclos

Choquesillo

ray structures of

V.M.; Niclós-Gutí Szewczuk Z.

to design kojic acid derivatives with new perspectives 569

M.; Lachowicz J.I. Gutiérrez

Dalton Trans.

Crisponi G.; Nurchi V.M.; Crespo Marques S.M.; Niclos

Choquesillo-Lazarte synthesized as iron che

Choquesillo-Lazarte

ray structures of

; Crisponi G.; Lachowicz J.I.; Gutí

Z. Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives

569

M.; Lachowicz J.I. Gutiérrez

Dalton Trans. 2011,

Lazarte synthesized as iron che

Lazarte

ISMEC 2013, June 16

ray structures of

Crisponi G.; Lachowicz J.I.; Gutíerrez

Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives

M.; Lachowicz J.I. Gutiérrez J.; Dominguez

2011,

Lazarte synthesized as iron che

Lazarte

ISMEC 2013, June 16

ray structures of the ligand and of some of its metal complexes will be also presented.

Crisponi G.; Lachowicz J.I.; errez

M.; Lachowicz J.I. J.; Dominguez

2011, 40(22), 5984

LazarteD.; Szewczuk Z. A family of hydroxypyrone ligands designed and synthesized as iron che

LazarteD.; Szewczuk Z. Searching for new aluminium chelating agents: a family of hydroxypyrone ligands.

ISMEC 2013, June 16

the ligand and of some of its metal complexes will be also presented.

Crisponi G.; Lachowicz J.I.; J.; González

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). 40(22), 5984

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and synthesized as iron chelators.

D.; Szewczuk Z. Searching for new aluminium chelating agents: a family of hydroxypyrone ligands.

ISMEC 2013, June 16

Crisponi G.; Lachowicz J.I.; ; González

Crisponi G.; Nurchi V.M.; Crespo Marques S.M.; Niclos-Gutierrez J.; Gonzalez

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and lators.

ISMEC 2013, June 16

Crisponi G.; Nurchi V.M.; Crespo Gutierrez J.; Gonzalez

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and lators.

Toso L.; Crisponi G.; Nurchi V.M.; Crespo M.A.; Marques S.M.;

Niclos-D.; Szewczuk Z. Searching for new aluminium chelating agents: a family of hydroxypyrone ligands.

ISMEC 2013, June 16

M.; Lachowicz J.I.; Crisponi G. J.; Dominguez

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and lators. J. Inorganic Biochemistry

Toso L.; Crisponi G.; Nurchi V.M.; Crespo

-Gutierrez J.; Gonzalez

ISMEC 2013, June 16

Crisponi G.; Lachowicz J.I.; ;

González-Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives

Crisponi G. J.; Dominguez-Martin

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). 40(22), 5984-5998

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and

J. Inorganic Biochemistry

Gutierrez J.; Gonzalez

D.; Szewczuk Z. Searching for new aluminium chelating agents: a family of hydroxypyrone ligands. J.

ISMEC 2013, June 16th

OC

Crisponi G.; Lachowicz J.I.;

-Pérez J.M.; Domínguez

Crisponi G. Martin

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). 5998

D.; Szewczuk Z. Searching for new aluminium chelating agents: a

th

– 20

OC-6

Crisponi G.; Lachowicz J.I.;

Pérez J.M.; Domínguez

Crisponi G. Martin

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). 5998.

Inorganic Biochemistry

20th

6

Crisponi G.; Lachowicz J.I.; Murgia S.; Pérez J.M.; Domínguez

Crisponi G.; A.;

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). Crisponi G.; Nurchi V.M.; Crespo

Toso L.; Crisponi G.; Nurchi V.M.;

Crespo-Gutierrez J.; Gonzalez

th

2013

Murgia S.; Pérez J.M.; Domínguez

; Murgia, ; Castineiras

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). Crisponi G.; Nurchi V.M.; Crespo-Alonso

-Alonso Gutierrez J.; Gonzalez

2013

Murgia, Castineiras

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). Alonso

Alonso Gutierrez J.; Gonzalez

2013 – Burgos (Spain

Murgia, Castineiras

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). Alonso

Gutierrez J.; Gonzalez-Perez J.M.; Dominguez

AlonsoM.; Lachowicz Gutierrez J.; Gonzalez

Burgos (Spain

Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives.

Murgia, S.; Castineiras

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). Alonso M.; Lachowicz

Perez J.M.; Dominguez

M.; Lachowicz

Gutierrez J.; Gonzalez-Perez J.M.; Dominguez

Acta of the International Symposia on Metal Complexes –

Burgos (Spain

Pivetta Pérez J.M.; Domínguez

Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed . J.

S.; Castineiras A.;

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). M.; Lachowicz

J. Inorganic Biochemistry, 2013

M.; Lachowicz

– ISMEC Acta, Volume 3 Burgos (Spain

Pivetta Pérez J.M.;

Domínguez-Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed Inorganic Biochemistry, Arca

A.;

2013

M.; Lachowicz

Inorganic Biochemistry,

ISMEC Acta, Volume 3 Burgos (Spain

Pivetta T.; -Martín

Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

norganic Biochemistry,

Arca Remelli

2013 accepted for publication

M.; Lachowicz

D.; Szewczuk Z. Searching for new aluminium chelating agents: a , 2013

ISMEC Acta, Volume 3 Burgos (Spain)

T.; Martín

M.; Remelli

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and accepted for publication M.; Lachowicz

2013

ISMEC Acta, Volume 3

Remelli M.; Martín

M.; Pintus Remelli

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and accepted for publication M.; LachowiczJ.I.: Arca M.; Santos

2013 submitted

Remelli M.; A.;

Pintus M.;

Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). M.; LachowiczJ.I.: Santos M.A.; Perez J.M.; Dominguez

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and accepted for publication

J.I.: Arca M.; Santos Perez J.M.; Dominguez

D.; Szewczuk Z. Searching for new aluminium chelating agents: a submitted

Remelli M.; ; Castiñeiras Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

Pintus

M.; Szewczuk, Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III).

J.I.: Santos M.A.; Perez J.M.; Dominguez

D.; Szewczuk Z. A family of hydroxypyrone ligands designed and accepted for publication

J.I.: Arca M.; Santos Perez J.M.; Dominguez

D.; Szewczuk Z. Searching for new aluminium chelating agents: a submitted

Remelli M.; Castiñeiras Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

Pintus A.; Szewczuk, Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III).

J.I.: Santos M.A.; Perez J.M.; Dominguez-Martin D.; Szewczuk Z. A family of hydroxypyrone ligands designed and

accepted for publication J.I.: Arca M.; Santos Perez J.M.;

Dominguez-D.; Szewczuk Z. Searching for new aluminium chelating agents: a submitted

Remelli M.; Rescigno Castiñeiras Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

A.; Gans Szewczuk, Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III).

J.I.: Santos M.A.; Martin D.; Szewczuk Z. A family of hydroxypyrone ligands designed and

accepted for publication J.I.: Arca M.; Santos

-Martin D.; Szewczuk Z. Searching for new aluminium chelating agents: a

Rescigno Castiñeiras Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

Gans Szewczuk, Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III).

J.I.: Santos M.A.; Martin D.; Szewczuk Z. A family of hydroxypyrone ligands designed and

Martin D.; Szewczuk Z. Searching for new aluminium chelating agents: a the ligand and of some of its metal complexes will be also presented.

Rescigno Castiñeiras A.; Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

2010, Gans Szewczuk, Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III).

J.I.: Santos M.A.; Martin A.; D.; Szewczuk Z. A family of hydroxypyrone ligands designed and

MartinA.; D.; Szewczuk Z. Searching for new aluminium chelating agents: a

53 the ligand and of some of its metal complexes will be also presented.

Rescigno A.; Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

2010,

P.; Z.; Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). J.I.: Santos M.A.;

A.; D.; Szewczuk Z. A family of hydroxypyrone ligands designed and accepted for publication

J.I.: Arca M.; Santos A.; D.; Szewczuk Z. Searching for new aluminium chelating agents: a

53 Rescigno A.; Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed

2010,

P.; Z.; Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III). J.I.: Santos M.A.; A.; D.; Szewczuk Z. A family of hydroxypyrone ligands designed and J.I.: Arca M.; Santos A.; D.; Szewczuk Z. Searching for new aluminium chelating agents: a

A New hydroxypyrone powerful chelator: from synthesis to Al<sup>III</sup>, Fe<sup>III</sup>, Cu<sup>II</sup> and Zn<sup>II</sup> complex formation equilibria, and structural characterization

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Guido Crisponi, Editor

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Begoña García

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ISMEC GROUP SERIES

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Begoña García

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Symposium Edition: XXI

Acta of the International Simposia on Metal Complex

Begoña García

Guido Crisponi, Editor

ISMEC GROUP SERIES

Volume:

Year: 201

ISSN:

Symposium Edition: XXI

Acta of the International Simposia on Metal Complex

Begoña García

Guido Crisponi, Editor

ISMEC GROUP SERIES

Volume:

Year: 201

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Symposium Edition: XXI

Acta of the International Simposia on Metal Complex

Begoña García

Guido Crisponi, Editor

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