Synthesis and Characterization of Ferrocene Acetals and Evaluation of Their Antineoplastic Properties by Using Breast Cancer Cell Lines In Vitro

Castillo-Ramirez, Jorge; Echevarría, Ileabett; Santiago, Janice; Pérez-Torres, Marianela; Rivera-Claudio, Mirna

doi:10.1055/s-0033-1338878

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2014

2022

Publication Types

Select...

Book2

Article1

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Synthesis of stableC-linked ferrocenyl amino acids and their use in solution-phase peptide synthesis

2015

View full text Add to dashboard Cite

Incorporation of ferrocenyl group to peptides is an efficient method to alter their hydrophobicity. Ferrocenyl group can also act as an electrochemical probe when incorporated onto functional peptides. Most often, ferrocene is incorporated onto peptides post-synthesis via amide, ester or triazole linkages. Stable amino acids containing ferrocene as a C-linked side chain are potentially useful building units for the synthesis of ferrocene-containing peptides. We report here an efficient route to synthesize ferrocene-containing amino acids that are stable and can be used in peptide synthesis. Coupling of 2-ferrocenyl-1,3-dithiane and iodides derived from aspartic acid or glutamic acid using n-butyllithium leads to the incorporation of a ferrocenyl unit to the δ-position or ε-position of an α-amino acid. The reduction or hydrolysis of the dithiane group yields an alkyl or an oxo derivative. The usability of the synthesized amino acids is demonstrated by incorporating one of the amino acids in both C-terminus and N-terminus of tripeptides in solution phase.

show abstract