Biological and biomedical aspects of metal phenolates

LI-JUNE MING

Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue CHE205, Tampa, Florida, 33620, USA

Fax: +1-813-974-1733; e-mail: ming@usf.edu

To

my mom on the occasion of her 90^th birthday and

my mother-in-law on the occasion of her 80^th birthday

I. INTRODUCTION

A. Acronyms and Abbreviations

B. Viewing Stereo Images

C. Phenols and Metal Phenolates in Biological Systems and Medicine

II. Metal Phenolates in BioMOLECULES AND PHARMACEUTICALS

A. Metal Complexes of Phenolates and Biomimetic Metal Phenolate Moieties

B. Phenol-Containing Biomolecules and Their Metal Complexes

1. Tyrosine and peptides

2. Catechol and its derivatives

3. Polyphenols and flavonoids

4. Siderophores and iron transport

5. Quinone derivatives

6. Salicylic acid and derivatives

7. Hydroxyphenyloxazoline and analogues

8. 8-Hydroxyquinoline, xanthurenic acid, and tryptophan

9. Metal phenolate analogues

C. Phenol-Containing Pharmaceuticals and Their Metal Complexes

1. Antibiotic and antitumor anthracyclines

2. Aureolic acids

3. Deferasirox, desferrithiocin, and miscellaneous agents for treatment of iron overload

4. Antibiotic 8-hydroxyquinoline and derivatives

5. Bioactive phenolate-containing complexes and analogues

6. Biosensors and imaging agents

III. METAL PHENOLATE MOIETIES IN PROTEINS AND ENZYMES

A. Metal Phenolate Moiety in Enzymes and Biological Processes

1. The astacin family

2. Purple acid phosphatases and related enzymes

3. Protocatechuate 3,4-dioxygenase and related enzymes

4. Heme-containing catalase

5. Heme-binding proteins

6. Transferrin, iron transport, and ferric-binding proteins

7. Metalloenzymes with a modified Tyr side chain

a. Galactose oxidase

b. Amine oxidase

c. Miscellaneous phenol moieties in metallo-biosystems

B. Enzymes Involved in Transformation of Aromatics

1. Biological transformation of aromatic compounds

a. Toluene 4-monooxygenase

b. Salicylate 1,2-dioxygenase

c. Homoprotocatechuate 2,3-dioxygenase

d. Heme monooxygenase

e. Polyketide cyclase

f. ‘Type-3’ copper enzymes

2. Tyrosine metabolism and tyrosinemia

C. Metal–Phenol Systems in Materials and Environmental Applications

1. Byssus and biomimetic adhesive materials

2. Protein-mineral interface

3. Degradation of aromatics and halogenated derivatives

a. Toluene 2,3-dioxygenase

b. Biphenyl 2,3-dioxygenase

c. 2,3-Dihydroxybiphenyl 1,2-dioxygenase

d. PCB and DDT

e. Bisphenol A

IV. REFERENCES