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Solid State Structures of Cadmium Complexes with Relevance for Biological Systems

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Cadmium: From Toxicity to Essentiality

Part of the book series: Metal Ions in Life Sciences ((MILS,volume 11))

Abstract

This chapter provides a review of the literature on structural information from crystal structures determined by X-ray diffractometry of cadmium(II) complexes containing ligands of potential biological interest. These ligands fall into three broad classes, (i) those containing N-donors such as purine or pyrimidine bases and derivatives of adenine, guanine or cytosine, (ii) those containing carboxylate groups such as α-amino acids, in particular the twenty essential ones, the water soluble vitamins (B-complex) or the polycarboxylates of EDTA type ligands, and (iii) S-donors such as thiols/thiolates or dithiocarbamates. A crystal and molecular structural analysis has been carried out for some representative complexes of these ligands, specifically addressing the coordination mode of ligands, the coordination environment of cadmium and, in some significant cases, the intermolecular interactions.

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Abbreviations

acv:

acyclovir[2-amine-9-(2-hydroxyethoxymethyl)-3H-purin-6-one

ap:

adipate(2–)

ATP:

adenosine 5’-triphosphate

BAL:

British Anti-Lewisite (2,3-dimercaptopropanol)

2,2’-bipy:

2,2’-bipyridine

4,4’-bipy:

4,4’-bipyridine

bpvbd:

3,6-bis(pivaloylamino)benzene-1,2-dithiolato-S,S’(2–)

CSD:

Cambridge Structural Database

DABT:

2,2’-diamino-4,4’-bis-1,3-thiazole

DMAB:

4-(dimethylamino)benzoate(1–)

DMF:

N,N-dimethylformamide

DMPS:

2,3-dimercapto-1-propanesulfonate (1–)

DMSA:

dimercaptosuccinate(2–)

dmso:

dimethylsulfoxide

dpe:

1,2-di(pyridin-4-yl)ethane

dppf:

(diphenylphosphino)ferrocene

ede-ade:

2-(ethylenediamine)ethyl-N9-adenine

ede-dap:

2-(ethylenediamine)ethyl-N9-2,6-diaminopurine

ede-gua:

2-(ethylenediamine)ethyl-N9-guanine

edp-dap:

2-(ethylenediamine)propyl-N9-2,6-diaminopurine

edt:

ethane-1,2-dithiolato

EDTA:

ethylenediamine-N,N,N’,N’-tetraacetate(4–)

en:

1,2-ethylenediamine

9Etgua:

9-ethylguanine

H6MP:

6-mercaptopurine

Hade:

adenine

Hala:

alanine

Hasn:

asparagine

Hasp:

aspartate

HBthiamine:

2-(α-hydroxybenzyl)thiamine

Hcyt:

cytosine

Hdap:

2,6-diaminopurine

Hgly:

glycine

Hgua:

guanine

Hhip:

hippuric acid

Hhyp:

hypoxanthine

Hhis:

histidine

Hicyt:

isocytosine

HIm:

1H-imidazole

Hmet:

methionine

Hphe:

phenylalanine

Hpro:

proline

Hptola:

p-toluic acid

Hpur:

purine

Hpym:

pyrimidine

Htheo:

theophiline

Htrp:

tryptophan

Hura:

uracil

Hxan:

xanthine

H2ap:

adipic acid

H2asp:

aspartic acid glycine

H2BAD+ :

N 6-benzyladeninium cation

H2cys:

cysteine

H2FAD+ :

N 6-furfuryladeninium cation

H2glu:

glutamic acid

H2tp:

terephthalic acid

IDA:

iminodiacetate(2–)

9Meade:

9-methyladenine

1Mecyt:

1-methylcytosine

9Megua:

9-methylguanine

NA:

nicotinate(1–)

NADA:

nicotinamide

NBO:

natural bond orbital programme

NBZ:

2-nitrobenzoate(1–)

niacin:

3-pyridinecarboxylic acid

niacinamide:

3-pyridinecarboxamide

NTA:

nitrilotriacetate(3–)

ox:

oxalate(2–)

o-PhDTA:

ortho-phenylenediamine-N,N,N’,N’-tetraacetate(4–)

paa:

2-pyridinealdazine

phen:

1,10-phenanthroline

PMAB:

4-(methylamino)benzoate(1–)

\( \text{PPh}_4^ + \) :

tetraphenylphosphonium

ptola:

p-toluic acid

S-2,4,6-iPr3C6H2 :

(2,4,6-tri-isopropyl)benzenethiolato(1–)

S-2,4,6,tbutyl C6H2 :

(2,4,6-tri-tert-butyl)benzenothiolato(1–)

SC6H4But-4:

4-tert-butylbenzenothiolato(1–)

ScHex:

cyclohexanethiolato(1–)

SCN:

thiocyanate

SPh = SC6H5 :

benzenothiolato(1–)

SPhF-3:

3-fluorobenzenethiolato(1–)

tem-N9,N9’-diade:

N 9,N 9-tetramethylene-bis(adenine)

3,4-TDTA:

3,4-toluenediamine-N,N,N’,N’-tetraacetate(4–)

tm-N9,N9’-diade:

N 9,N 9′-trimethylene-bis(adenine)

1Toscyt:

1-(p-toluenesulfonyl)cytosine

tp:

terephthalate(2–)

tren:

tris-(2-aminoethyl)amine

trp:

tryptophan

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Acknowledgments

Research in the authors’ laboratories is funded by the Ministry of Science and Innovation and FEDER-EC (MAT2010-15594), Xunta de Galicia (INCITE08PXIB203128PR and 10TMT314002PR) and the University of Granada (Domestic Grant P18-2009). We also thank Professors Dr. J. M. González-Pérez and Dr. E. Vázquez-López for critically reading of the manuscript. ADM thanks the Ministry of Education for a FPU Ph.D. fellowship. The authors thank their current and former graduate students and post-doctoral fellows for their hard work and valuable discussion on this project.

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Authors and Affiliations

  1. Departamento de Química Inorgánica, Facultad de Química, Universidad de Vigo, E-36310, Vigo, Spain

    Rosa Carballo

  2. Departamento de Química Inorgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, Spain

    Alfonso Castiñeiras & Isabel García-Santos

  3. Departamento de Química Inorgánica, Facultad de Farmacia, Universidad de Granada, E-18071, Granada, Spain

    Alicia Domínguez-Martín & Juan Niclós-Gutiérrez

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  1. Rosa Carballo
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Correspondence to Alfonso Castiñeiras .

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  1. Inorganic Chemistry, Chemistry, Universität Basel, Spitalstr. 51, Basel, 4056, Basel Stadt, Switzerland

    Astrid Sigel

  2. Inst. Anorganische Chemie, Universität Basel, Spitalstr. 51, Basel, 4056, Switzerland

    Helmut Sigel

  3. Institute of Inorganic Chemistry, University of Zürich, Winterthurerstrasse 190, Zürich, 8057, Zürich, Switzerland

    Roland KO Sigel

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Carballo, R., Castiñeiras, A., Domínguez-Martín, A., García-Santos, I., Niclós-Gutiérrez, J. (2013). Solid State Structures of Cadmium Complexes with Relevance for Biological Systems. In: Sigel, A., Sigel, H., Sigel, R. (eds) Cadmium: From Toxicity to Essentiality. Metal Ions in Life Sciences, vol 11. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-5179-8_7

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