Syntheses and properties of bioactive organo-silicon compounds

Tacke, Reinhold; Wannagat, U.

doi:10.1007/bfb0048522

Cited by 96 publications

(21 citation statements)

References 60 publications

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“…The perspective top view and the structural parameters clearly reveal the presence of pbonding interaction between N and Si atoms. The coplanarity of the dimethylaminosilylene constituents Si, N, C (16), and C (17) atoms as indicated by the sum of 358.4°for three angles around the N atom and the short N-Si distance of 1.705(3) Å compared to the usual N-Si single bond distance of 1.80 Å [16] are strong indication of the foregoing p-bonding interaction between N and Si atoms. According to the DFT calculation results, the N-Si bonding orbital is highly polarized toward N atom and the lone pair electrons of the N atom strongly interact with r* orbital of the Si-C(15) bond, confirming the presence of p-bonding interaction as observed in the crystal structure ( Fig.…”

Section: Resultsmentioning

confidence: 98%

Aminosilylene-bridged ansa-zirconocenes for branched polyethylenes with bimodal molecular weight distributions

Han

Kim

Lee

et al. 2009

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 98%

Aminosilylene-bridged ansa-zirconocenes for branched polyethylenes with bimodal molecular weight distributions

Han

Kim

Lee

et al. 2009

Journal of Organometallic Chemistry

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“…(iv) Carbon and silicon also differ in their electronic properties; according to the Pauling scale, silicon is more electropositive (1.8) than carbon (2.5), which leads to differences of bond polarizations. (v) Finally, silicon strongly increases the lipophilicity of compounds when compared to their carbon-containing analogues . However, in some cases, this increased lipophilicity might be a limitation for a compound’s water solubility, which is a major concern in medicinal chemistry.…”

Section: Silyl Amino Acidsmentioning

confidence: 99%

“…(v) Finally, silicon strongly increases the lipophilicity of compounds when compared to their carbon-containing analogues. 12 However, in some cases, this increased lipophilicity might be a limitation for a compound's water solubility, which is a major concern in medicinal chemistry.…”

Section: Silyl Amino Acidsmentioning

confidence: 99%

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

et al. 2016

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Unnatural α-amino acids form a family of essential molecules used for, among other applications, the synthesis of modified peptides, to improve resistance to proteolytic enzyme degradation, and to modulate physico- and biochemical properties of bioactive peptides as well as chiral inducers in asymmetric synthesis. Among them, silicon-containing unnatural amino acids are becoming an interesting new class of building blocks. The replacement of carbon atoms in bioactive substances with silicon is becoming increasingly popular. Peptides containing silyl amino acids hold great promise for maintaining or reinforcing the biological activity of active compounds, while they simultaneously enhance their resistance to enzyme degradation. In addition, the lipophilicity of the silicon atom facilitates their membrane crossing and their bioavailability. Nowadays, the interest of the pharmaceutical industry in peptide- and protein-based therapies is increasing. In this respect, silicon-containing amino acids and peptides are likely to be a significant part of future innovations in this area, and more generally in the area of biomolecules. In this process, commercial availability of silicon-containing amino acids is necessary: new syntheses have been developed, and work in this area is ongoing. This review aims to be a comprehensive and general summary of the different methods used to prepare silicon-containing amino acids and their implications on conformational structures and biological applications when they are incorporated into bioactive molecules.

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“…Silicon and carbon (C) are members of group IV of the Periodic Table of the Elements and share some similarities in their chemistry. The preparation of biologically active organosilicon compounds containing at least one Si-C bond has been an area of investigation for decades [Chiu et al, 1982;Fessenden and Ahlfors, 1967;, 1965, 1966Fessenden and Hartman, 1970;Fessenden and Rittenhouse, 1968;Showell et al, 2006;Tacke, 1977;Tacke and Wannagat, 1977;Tacke and Wannagat, 1979;Tacke and Zilch, 1986]. Silicon and carbon, however, have important chemical differences [Bertrand, 2004]:…”

Section: Bioorganosilicon Chemistrymentioning

confidence: 99%

Novel therapeutics with enhanced biological activity generated by the strategic introduction of silicon isosteres into known drug scaffolds

Gately

West

2007

Drug Development Research

146

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The strategic replacement of carbon with silicon within biologically prevalidated drug scaffolds can generate focused libraries of pharmaceutically relevant agents with novel, durable and marketable intellectual property. This approach can be cost-effective and of lower developmental risk because known drugs have recognized pharmacology and toxicity profiles, proven safety in humans, and established manufacturing and formulation methods. The change in shape, charge, and lipophilicity that can result from the addition of silicon can favorably alter the biological activity and toxicology of the parent drug. Silicon-containing derivatives of indomethacin are COX-2 selective, suggesting they will not be associated with the classical toxicities associated with nonselective inhibition of the cyclooxygenases. The silicon-indomethacin derivatives also demonstrated superior anti-cancer activity at clinically achievable concentrations when tested in vitro against a human pancreatic cancer cell line, MiaPaCa-2, and a panel of 14 human multiple myeloma cell lines. Bioorganosilicon chemistry represents an attractive approach for emerging biopharmaceutical organizations seeking to rapidly develop a portfolio of novel pharmacological agents that have the potential for enhanced therapeutic and pharmacological benefit. Drug Dev Res 68: [156][157][158][159][160][161][162][163] 2007 r2007 Wiley-Liss, Inc.

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Syntheses and properties of bioactive organo-silicon compounds

Cited by 96 publications

References 60 publications

Aminosilylene-bridged ansa-zirconocenes for branched polyethylenes with bimodal molecular weight distributions

Aminosilylene-bridged ansa-zirconocenes for branched polyethylenes with bimodal molecular weight distributions

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

Novel therapeutics with enhanced biological activity generated by the strategic introduction of silicon isosteres into known drug scaffolds

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