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Gérard Jaouen - One of the best experts on this subject based on the ideXlab platform.

  • Review on Bioorganometallic Chemistry and New Outcomes in the Synthesis and Substitution of Tetracarbonyl(pyrrolylimine) Complexes of Rhenium with Organophosphorus Ligands
    Current topics in medicinal chemistry, 2017
    Co-Authors: Antoine Simonneau, Franck Le Bideau, Jean-hugues Mirebeau, Jérôme Marrot, Gérard Jaouen
    Abstract:

    : After a short review dealing with Bioorganometallic Chemistry, the synthesis of tetracarbonyl (pyrrolylimine) complexes of rhenium bearing chirality on the pyrrolyl ligands was reported.The reactivity of these compounds towards the substitution of one carbonyl ligand with triphenyl phosphine, tricyclohexyl phosphine and trimethyl phosphite was studied. The rhenium becoming a stereogenic center in that transformation, the resulting tricarbonyl species were obtained as mixtures of diastereomers, with diastereomeric excesses varying from 8 to 84%, according to the reaction conditions and the relative steric hindrances of the pyrrolylimine and the organophosphorus ligands. These Bioorganometallics are potential CO releasing molecules that could be used in the field of medicinal Chemistry.

  • Bioorganometallic Chemistry applications in drug discovery biocatalysis and imaging
    2015
    Co-Authors: Gérard Jaouen, Michele Salmain
    Abstract:

    Preface PART I: Medicinal Chemistry ORGANOMETALLIC COMPLEXES AS ENZYME INHIBITORS: A CONCEPTUAL OVERVIEW Introduction Organometallic Compounds as Inert Structural Scaffolds for Enzyme Inhibition Organometallic Compounds Targeting Specific Protein Residues The Bioisosteric Substitution Novel Mechanisms of Enzyme Inhibition with Organometallic Compounds Organometallic Compounds as Cargo Delivers of Enzyme Inhibitors Organometallic Enzyme Inhibitors for Theranostic Purposes Conclusion THE BIOLOGICAL TARGET POTENTIAL OF ORGANOMETALLIC STEROIDS Introductory Note on Nuclear Receptors Steroids and Organometallics: An Overview of the Transitional Period from the Use of Organometallics in Synthesis to the Emergence of Bioorganometallics Epilog CHIRALITY IN ORGANOMETALLIC ANTICANCER COMPLEXES Introduction Chirality in Arene Complexes CIP System for the Nomenclature of Chiral-at-Metal Arene Complexes Chiral Organometallic Complexes as Anticancer Agents Half-Sandwich Complexes with Chiral Metal Centers Conclusions GOLD ORGANOMETALLICS WITH BIOLOGICAL PROPERTIES Introduction: The Use of Gold in Medicine Anticancer Gold Organmetallics and Proposed Biological Targets Conclusions and Perspectives ON THE MOLECULAR MECHANISMS OF THE ANTIMALARIAL ACTION OF FERROQUINE History and Development Mechanism(s) of Action 4-Aminoquinoline Antimalarials Mechanism(s) of Action of Ferroquine as an Antimalarial Conclusion METAL CARBONYL PRODRUGS: CO DELIVERY AND BEYOND Introducing CO in Biology Therapeutic Delivery of CO Biological and Therapeutic Results Obtained with the Early-Stage CORMs Beyond the Early-Stage CORMs: Strategies for Finding New Candidates Intracellular Detection of CORMs, Mechanistic Studies, and Other Unanswered Questions Designing Pharmacologically Useful, Drug-like CORMs Final Remarks and Perspectives DINITROSYL IRON COMPLEXES WITH NATURAL THIOL-CONTAINING LIGANDS: PHYSICOChemistry, BIOLOGY, AND MEDICINE Introduction The History of Detection and Identification of DNIC with Thiol-Containing Ligands in Microorganisms and Animal Tissues PhysicoChemistry of DNIC with Natural Thiol-Containing Ligands Biological Effects of DNIC with Thiol-Containing Ligands DNIC with Thiol-Containing Ligands as a Basis in the Design of Drugs with a Broad Range of Therapeutic Activities PART II: Metalloproteins, Catalysis, and Energy Production THE Bioorganometallic Chemistry OF HYDROGENASE Introduction Structure and Function Natural Biosynthesis and Synthetic Analogs of the Active Sites Comments and Conclusion BIO-ORGANOMETALLIC SYSTEMS FOR THE HYDROGEN ECONOMY: ENGINEERING OF ELECTRODE MATERIALS AND LIGHT-DRIVEN DEVICES Introduction Electrode Materials for Hydrogen Evolution and Uptake Light-Driven Systems for Hydrogen Evolution Artificial Photosynthetic Systems Summary and Conclusions ARTIFICIAL METALLOENZYMES CONTAINING AN ORGANOMETALLIC ACTIVE SITE Introduction Dative Anchoring Supramolecular Anchoring Covalent Anchoring Mixed Anchoring Modes Peptide Scaffolds Summary and Outlook PART III: Bioanalysis ORGANOMETALLIC BIOPROBES FOR CELLULAR IMAGING Introduction Luminescence Vibrational Spectroscopy Miscellaenous Conclusions Index

  • Bioorganometallic Chemistry: Applications in Drug Discovery Biocatalysis, and Imaging - The Biological Target Potential of Organometallic Steroids
    Bioorganometallic Chemistry, 2014
    Co-Authors: Gérard Jaouen, Siden Top, Michael J. Mcglinchey
    Abstract:

    The discovery of the superfamily of nuclear receptors, represented first by the estrogen receptor (ERα) identified by E.V. Jensen in 1958, caused a veritable revolution in biology. Its repercussions are still with us, in the Chemistry of steroids, synthetic selective steroid receptor modulators, and endocrine disruptors. These small molecules, including the group of steroids we will focus on here, can be linked to major diseases (e.g., cancers, osteoporosis, and diabetes), as well as issues relating to fertility and conception, birth control, and environmental diseases. After a brief description of the mechanism of action of the nuclear receptors we will address the issue of the organometallic versions of molecules that can potentially target these receptors, as well as their biological advantages. We have shown via radioactive labeling that certain organometallic hormone complexes have good targeting ability for nuclear receptors. The reversible binding of these complexes with specific receptors as well as the case of irreversible inhibition of estrogen receptors that can sometimes be obtained using carefully selected organometallic moieties will be discussed in this chapter. This work introduces the approach using SERMs, SARMs, and so on, which due to their large numbers are only touched on here. A section gives more complete details of organometallic radiopharmaceuticals, mostly steroidal. In broader strokes the current renaissance underway in the area of organometallic steroids is discussed with emphasis on biological aspects where known. Finally, some directions are indicated concerning new organometallic bioprobes obtained with SERMs and other endocrine disruptors that make new types of analysis possible. This combined with endocrine modulators possessing an additional organometallic function, for example of the redox type, points to a future that looks to be rich in promise.

  • Recent Analytical Applications of Molecular Spectroscopy in Bioorganometallic Chemistry—Part I: Metal Carbonyls
    Applied Spectroscopy Reviews, 2012
    Co-Authors: Ian S. Butler, Gérard Jaouen, Rosine P. Kengne-momo, Clotilde Policar, Anne Vessières
    Abstract:

    This is the first part of a two-part review on the analytical applications of molecular spectroscopy in Bioorganometallic Chemistry since 2005. In this case, radiopharmaceutical studies are included and the review is focused particularly on biological molecules labeled with metal carbonyl fragments.

  • Recent Analytical Applications of Molecular Spectroscopy in Bioorganometallic Chemistry-Part I: Metal Carbonyls
    Applied Spectroscopy Reviews, 2012
    Co-Authors: Ian S. Butler, Gérard Jaouen, Rosine P. Kengne-momo, Clotilde Policar, Anne Vessières
    Abstract:

    This is the first part of a two-part review on the analytical applications of molecular spectroscopy in Bioorganometallic Chemistry since 2005. In this case, radiopharmaceutical studies are included and the review is focused particularly on biological molecules labeled with metal carbonyl fragments.

Richard H Fish - One of the best experts on this subject based on the ideXlab platform.

  • Organometallic Chemistry at the Interface with Biology
    Advances in Bioorganometallic Chemistry, 2019
    Co-Authors: Richard H Fish
    Abstract:

    Abstract We will review various perspectives of our Bioorganometallic Chemistry studies that included reactions of organotin compounds with cytochrome P450 enzymes, and their Mn/Fe porphyrin biomimics to provide regioselective C-OH compounds; reactions of a Cp*Rh tris aqua dicationic complex, [Cp*Rh(H2O)3](OTf)2, with nucleobases/NAD+, as a function of pH; supramolecular Cp*Rh-nucleobase complexes in host-guest Chemistry in water; chemoselective reduction of NAD+ biomimetics with an in situ formed [Cp*Rh(bpy)H](OTf) to provide 1,4-NADH biomimetic co-factors, in tandem with HLADH enzymatic catalysis for stereoselective reductions of achiral ketones to chiral S-alcohols, as well as oxidation reactions with mutant cytochrome P450 enzymes; synthesis, DFT mechanism, and bioassays of organorhodium-hydroxytamoxifen complexes as potential breast cancer pharmaceuticals; and synthesis and bioactivity of Cp*Rh-tyrosine selective G-Protein-Coupled Receptor Peptide complexes, including molecular docking studies of the [(η6-Cp*Rh-Tyr1)-Leu-Enkephalin]2+ complex to the X-ray crystallographic defined, µ-, ∂-, and κ−Opioid receptors.

  • A Bioorganometallic Chemistry perspective: Organometallic Chemistry at the interface with biology
    Journal of Organometallic Chemistry, 2015
    Co-Authors: Richard H Fish
    Abstract:

    Abstract A 41 year perspective on our Bioorganometallic Chemistry studies that included reactions of organotin compounds with cytochrome P450 enzymes, and their biomimics; identification of natural organoarsenic compounds in oil shale; reactions of an Cp*Rh tris aqua complex with nucleobases; supramolecular Cp*Rh-nucleobase complexes in host-guest Chemistry; chemoselective reduction of NAD+ biomimetic co-factors with an Cp*Rh-hydride to provide 1,4-NADH biomimics, in tandem with enzymatic catalysis for stereoselective reductions of achiral ketones to chiral alcohols, and including oxidation reactions with cytochrome P450 enzymes; synthesis and bioassays of organorhodium-hydroxytamoxifen breast cancer pharmaceuticals; and synthesis and bioactivity of Cp*Rh-G-Protein Coupled Receptor peptides, will be presented in this 2014 ISBOMC Award Paper.

  • a Bioorganometallic Chemistry overview from cytochrome p450 enzyme metabolism of organotin compounds to organorhodium hydroxytamoxifen complexes with potential anti cancer properties a 37 year perspective at the interface of organometallic Chemistry
    Australian Journal of Chemistry, 2010
    Co-Authors: Richard H Fish
    Abstract:

    A 37 year perspective on Bioorganometallic Chemistry studies, which included metabolism of organotin compounds with cytochrome P450 enzymes, and their biomimics; reactions of organorhodium aqua complexes with nucleobases, nucleosides, and nucleotides; supramolecular organorhodium-nucleobase complexes as hosts for aromatic amino acid and aromatic carboxylic acid guests; regioselective reduction of NAD+ biomimics with an organorhodium hydride; tandem catalysis of an organorhodium hydride reduction to provide a 1,4-NADH biomimic for horse liver dehydrogenase stereoselective reduction of achiral ketones to chiral alcohols, and oxidation reactions with cytochrome P450 enzymes; and organorhodium-hydroxytamoxifen pharmaceuticals, will be presented. Each of these areas of Bioorganometallic Chemistry will be briefly discussed in this personal synopsis of the new, important, and exciting field of Bioorganometallic Chemistry, and its impact on metal-based drug research.

  • Bioorganometallic Chemistry biocatalytic oxidation reactions with biomimetic nad nadh co factors and cp rh bpy h for selective organic synthesis
    Journal of Organometallic Chemistry, 2004
    Co-Authors: Jochen Lutz, Richard H Fish, Frank Hollmann, Adrian Schnyder, Andreas Schmid
    Abstract:

    The biocatalytic, regioselective hydroxylation of 2-hydroxybiphenyl to the corresponding catechol was accomplished utilizing the monooxygenase 2-hydroxybiphenyl 3-monooxygenase (HbpA). The necessary natural nicotinamide adenine dinucleotide (NAD{sup +}) co-factor for this biocatalytic process was replaced by a biomimetic co-factor, N-benzylnicotinamide bromide, 1a. The interaction between the flavin (FAD) containing HbpA enzyme and the corresponding biomimetic NADH compound, N-benzyl-1,4-dihdronicotinamide, 1b, for hydride transfers, was shown to readily occur. The in situ recycling of the reduced NADH biomimic 1b from 1a was accomplished with [Cp*Rh(bpy)H](Cl); however, productive coupling of this regeneration reaction to the enzymatic hydroxylation reaction was not totally successful, due to a deactivation process concerning the HbpA enzyme peripheral groups; i.e., -SH or -NH{sub 2} possibly reacting with the precatalyst, [Cp*Rh(bpy)(H{sub 2}O)](Cl){sub 2}, and thus inhibiting the co-factor regeneration process. The deactivation mechanism was studied, and a promising strategy of derivatizing these peripheral -SH or -NH{sub 2} groups with a polymer containing epoxide was successful in circumventing the undesired interaction between HbpA and the precatalyst. This latter strategy allowed tandem co-factor regeneration using 1a or 2a, [Cp*Rh(bpy)(H2O)](Cl){sub 2}, and formate ion, in conjunction with the polymer bound, FAD containing HbpA enzyme to provide the catechol product.

  • Bioorganometallic Chemistry: biocatalytic oxidation reactions with biomimetic nad+/nadh co-factors and [cp*rh(bpy)h]+ for selective organic synthesis
    Journal of Organometallic Chemistry, 2004
    Co-Authors: Jochen Lutz, Richard H Fish, Frank Hollmann, Adrian Schnyder, Andreas Schmid
    Abstract:

    The biocatalytic, regioselective hydroxylation of 2-hydroxybiphenyl to the corresponding catechol was accomplished utilizing the monooxygenase 2-hydroxybiphenyl 3-monooxygenase (HbpA). The necessary natural nicotinamide adenine dinucleotide (NAD{sup +}) co-factor for this biocatalytic process was replaced by a biomimetic co-factor, N-benzylnicotinamide bromide, 1a. The interaction between the flavin (FAD) containing HbpA enzyme and the corresponding biomimetic NADH compound, N-benzyl-1,4-dihdronicotinamide, 1b, for hydride transfers, was shown to readily occur. The in situ recycling of the reduced NADH biomimic 1b from 1a was accomplished with [Cp*Rh(bpy)H](Cl); however, productive coupling of this regeneration reaction to the enzymatic hydroxylation reaction was not totally successful, due to a deactivation process concerning the HbpA enzyme peripheral groups; i.e., -SH or -NH{sub 2} possibly reacting with the precatalyst, [Cp*Rh(bpy)(H{sub 2}O)](Cl){sub 2}, and thus inhibiting the co-factor regeneration process. The deactivation mechanism was studied, and a promising strategy of derivatizing these peripheral -SH or -NH{sub 2} groups with a polymer containing epoxide was successful in circumventing the undesired interaction between HbpA and the precatalyst. This latter strategy allowed tandem co-factor regeneration using 1a or 2a, [Cp*Rh(bpy)(H2O)](Cl){sub 2}, and formate ion, in conjunction with the polymer bound, FAD containing HbpA enzyme to provide the catechol product.

Bo Han - One of the best experts on this subject based on the ideXlab platform.

Christophe Biot - One of the best experts on this subject based on the ideXlab platform.

  • Organometallic complexes: new tools for chemotherapy.
    Current medicinal chemistry, 2010
    Co-Authors: Chavain N, Christophe Biot
    Abstract:

    The importance of organometallics can be noticed by their presence in all life organisms. The most known natural organometallic molecule is vitamin B12, a porphyrin containing a cobalt atom, useful for several enzymatic trans- formations. Based on the remarkable properties of this class of compounds, a new area of medicinal research was devel- oped. Gerard Jaouen was the first to introduce the term of "Bioorganometallic Chemistry" in 1985 although the first or- ganometallic therapeutical was Salvarsan®, discovered by Paul Ehrlich (Nobel Prize in Medicine in 1908). Bioor- ganometallic Chemistry consists of the synthesis and the study of organometallic complexes, complexes with at least one metal-carbon bond, in a biological and medicinal interest. This field of research was accentuated by the discovery of the ferrocene in 1951 by Pauson and Kealy, confirmed in 1952 by Wilkinson (Nobel Prize in 1973). Today, Bioorganometallic Chemistry includes 5 main domains: (1) organometallic therapeuticals, (2) toxicology and environment, (3) molecular rec- ognition in aqueous phases, (4) enzymes, proteins and peptides, (5) bioanalysis and pharmaceutical sensors. In this re- view, we focused on organometallic therapeuticals. The exceptional properties of organometallics are first described and then, an overview on the main organometallic complexes used for drug design is presented. This review gives an idea how organometallics can be used for the rational design of new drugs.

  • Bioorganometallic Chemistry and Malaria
    Topics in Organometallic Chemistry, 2010
    Co-Authors: Christophe Biot, Daniel Dive
    Abstract:

    This chapter summarizes recent developments in the design, synthesis, and structure–activity relationship studies of organometallic antimalarials. It begins with a general introduction to malaria and the biology of the parasite Plasmodium falciparum, with a focus on the heme detoxification system. Then, a number of metal complexes from the literature are reported for their antiplasmodial activity. The second half of the chapter deals with the serendipitous discovery of ferroquine, its mechanism(s) of action, and the failure to induce a resistance. Last, but not least, we suggest that the Bioorganometallic approach offers the potential for the design of novel therapeutic agents.

  • Organometallic complexes: New tools for chemotherapy
    Current Medicinal Chemistry, 2010
    Co-Authors: Natascha Chavain, Christophe Biot
    Abstract:

    The importance of organometallics can be noticed by their presence in all life organisms. The most known natural organometallic molecule is vitamin B12, a porphyrin containing a cobalt atom, useful for several enzymatic transformations. Based on the remarkable properties of this class of compounds, a new area of medicinal research was developed. Gérard Jaouen was the first to introduce the term of "Bioorganometallic Chemistry" in 1985 although the first organometallic therapeutical was Salvarsan ®, discovered by Paul Ehrlich (Nobel Prize in Medicine in 1908). Bioorganometallic Chemistry consists of the synthesis and the study of organometallic complexes, complexes with at least one metal-carbon bond, in a biological and medicinal interest. This field of research was accentuated by the discovery of the ferrocene in 1951 by Pauson and Kealy, confirmed in 1952 by Wilkinson (Nobel Prize in 1973). Today, Bioorganometallic Chemistry includes 5 main domains: (1) organometallic therapeuticals, (2) toxicology and environment, (3) molecular recognition in aqueous phases, (4) enzymes, proteins and peptides, (5) bioanalysis and pharmaceutical sensors. In this review, we focused on organometallic therapeuticals. The exceptional properties of organometallics are first described and then, an overview on the main organometallic complexes used for drug design is presented. This review gives an idea how organometallics can be used for the rational design of new drugs.

  • Enhancement of the antimalarial activity of ciprofloxacin using a double prodrug/Bioorganometallic approach
    Journal of Medicinal Chemistry, 2009
    Co-Authors: Faustine Dubar, Daniel Dive, G Anquetin, Bruno Pradines, Jamal Khalife, Christophe Biot
    Abstract:

    The derivatization of the fluoroquinolone ciprofloxacin greatly increases its antimalarial activity by combining Bioorganometallic Chemistry and the prodrug approach. Two new achiral compounds 2 and 4 were found to be 10- to 100-fold more active than ciprofloxacin against Plasmodium falciparum chloroquinesusceptible and chloroquine-resistant strains. These achiral derivatives killed parasites more rapidly than did ciprofloxacin. Compounds 2 and 4 were revealed to be promising leads, creating a new family of antimalarial agents.

  • enhancement of the antimalarial activity of ciprofloxacin using a double prodrug Bioorganometallic approach
    Journal of Medicinal Chemistry, 2009
    Co-Authors: Faustine Dubar, Daniel Dive, G Anquetin, Bruno Pradines, Jamal Khalife, Christophe Biot
    Abstract:

    The derivatization of the fluoroquinolone ciprofloxacin greatly increases its antimalarial activity by combining Bioorganometallic Chemistry and the prodrug approach. Two new achiral compounds 2 and 4 were found to be 10- to 100-fold more active than ciprofloxacin against Plasmodium falciparum chloroquine-susceptible and chloroquine-resistant strains. These achiral derivatives killed parasites more rapidly than did ciprofloxacin. Compounds 2 and 4 were revealed to be promising leads, creating a new family of antimalarial agents.

Yuehua Zhang - One of the best experts on this subject based on the ideXlab platform.