Progress in the Synthesis and Bioactivity of Hexacoordinate Silicon(IV) Complexes

Henker, Jens; Wirmer‐Bartoschek, Julia; Bendel, Lars Erik; Xiang, Yonggang; Fu, Chen; Harms, Klaus; Schwalbe, Harald; Meggers, Eric

doi:10.1002/ejic.201600953

Cited by 12 publications

(5 citation statements)

References 49 publications

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“…DNA intercalators have a variety of therapeutic applications mainly in the area of cancer therapy . A follow-up of this work led to the synthesis of several hexacoordinate silicon complexes, and NMR spectroscopy studies proved that they bind to G-quadruplex DNA . Because of nontoxicity and natural abundance, use of silicon is advantageous over the commonly used transition metals in designing complexes with pharmaceutical applications.…”

Section: Novel Chemical Space Provided By Siliconmentioning

confidence: 99%

Quest for Novel Chemical Entities through Incorporation of Silicon in Drug Scaffolds

2017

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In order to optimize a lead molecule for further development, bioisosteric replacements are generally adopted as one of the strategies. Silicon appears to be the right choice as a carbon isostere because of the similarity in chemical properties. Silicon can be strategically introduced in a molecule to modulate its druglike properties, providing medicinal chemists with an unconventional strategy for replacing a carbon atom. Silicon can also be introduced to replace other heteroatoms and can act as a surrogate of functional groups such as olefin and amide as well. The present Perspective focuses on the opportunities that silicon incorporation offers in drug discovery, with an emphasis on case studies where introduction of silicon has created a benefit over its analog. We have tried to highlight all the recent developments in the field and briefly discuss the challenges associated with them.

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Section: Novel Chemical Space Provided By Siliconmentioning

confidence: 99%

Quest for Novel Chemical Entities through Incorporation of Silicon in Drug Scaffolds

2017

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“…Hydrolytically stable hexacoordinate silicon complexes have been shown to serve as nontoxic DNA intercalators. , Silicon is less toxic and costly than transition metals, and thus, there is value in developing biologically active coordination complexes using Si rather than other metals. However, syntheses of hexavalent Si typically rely on intermediates unstable in water, and new chemical strategies would need to be developed to construct these molecules biocatalytically.…”

Section: Opportunities For Biocatalysis To Impact Organosilicon Chemi...mentioning

confidence: 99%

Biocatalytic Transformations of Silicon—the Other Group 14 Element

et al. 2021

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Significant inroads have been made using biocatalysts to perform new-to-nature reactions with high selectivity and efficiency. Meanwhile, advances in organosilicon chemistry have led to rich sets of reactions holding great synthetic value. Merging biocatalysis and silicon chemistry could yield new methods for the preparation of valuable organosilicon molecules as well as the degradation and valorization of undesired ones. Despite silicon’s importance in the biosphere for its role in plant and diatom construction, it is not known to be incorporated into any primary or secondary metabolites. Enzymes have been found that act on silicon-containing molecules, but only a few are known to act directly on silicon centers. Protein engineering and evolution has and could continue to enable enzymes to catalyze useful organosilicon transformations, complementing and expanding upon current synthetic methods. The role of silicon in biology and the enzymes that act on silicon-containing molecules are reviewed to set the stage for a discussion of where biocatalysis and organosilicon chemistry may intersect.

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“…Silicon can form stable structures inaccessible to carbon, such as stable gem diols, which have been shown to both be stable in water and to be pharmacologically promising [57] (see also Section 4.1). Silyl fluorides have also shown specific biological effects [58], as have other, more exotic, molecules like hexa-coordinate silicon (10) [59].…”

Section: Observed Functional Diversity Of Silicon Chemistrymentioning

confidence: 99%

“…The diminished structural chemical diversity of silicon chemistry due to the lack of unsaturated functional groups is not compensated by the fact that silicon forms some unique compounds that do not have stable carbon analogues. For example, penta-and hexa-coordinate Si compounds are stable [23,59,220]. ((Arenediolato)bis(polypyridyl)silicon(IV) complexes (10) contain hexa-coordinate silicon and are surprisingly stable against hydrolysis in water and are investigated as potential DNA binders [59].)…”

Section: Appendix C Formation Of Unsaturated Organosilicon Compoundsmentioning

confidence: 99%

“…For example, penta-and hexa-coordinate Si compounds are stable [23,59,220]. ((Arenediolato)bis(polypyridyl)silicon(IV) complexes (10) contain hexa-coordinate silicon and are surprisingly stable against hydrolysis in water and are investigated as potential DNA binders [59].) Silanediols have been developed as protease inhibitors and are water-stable as well [99].…”

Section: Appendix C Formation Of Unsaturated Organosilicon Compoundsmentioning

confidence: 99%

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On the Potential of Silicon as a Building Block for Life

Petkowski

Bains

Seager

2020

Life

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Despite more than one hundred years of work on organosilicon chemistry, the basis for the plausibility of silicon-based life has never been systematically addressed nor objectively reviewed. We provide a comprehensive assessment of the possibility of silicon-based biochemistry, based on a review of what is known and what has been modeled, even including speculative work. We assess whether or not silicon chemistry meets the requirements for chemical diversity and reactivity as compared to carbon. To expand the possibility of plausible silicon biochemistry, we explore silicon’s chemical complexity in diverse solvents found in planetary environments, including water, cryosolvents, and sulfuric acid. In no environment is a life based primarily around silicon chemistry a plausible option. We find that in a water-rich environment silicon’s chemical capacity is highly limited due to ubiquitous silica formation; silicon can likely only be used as a rare and specialized heteroatom. Cryosolvents (e.g., liquid N2) provide extremely low solubility of all molecules, including organosilicons. Sulfuric acid, surprisingly, appears to be able to support a much larger diversity of organosilicon chemistry than water.

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Progress in the Synthesis and Bioactivity of Hexacoordinate Silicon(IV) Complexes

Cited by 12 publications

References 49 publications

Quest for Novel Chemical Entities through Incorporation of Silicon in Drug Scaffolds

Quest for Novel Chemical Entities through Incorporation of Silicon in Drug Scaffolds

Biocatalytic Transformations of Silicon—the Other Group 14 Element

On the Potential of Silicon as a Building Block for Life

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