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Biological Evaluation and Conformational Preferences of Ferrocene Dipeptides with Hydrophobic Amino Acids

Kovačević, Monika; Čakić Semenčić, Mojca; Kodrin, Ivan; Roca, Sunčica; Perica, Jana; Mrvčić, Jasna; Stanzer, Damir; Molčanov, Krešimir; Milašinović, Valentina; Brkljačić, Lidija; Barišić, Lidija (2023) Biological Evaluation and Conformational Preferences of Ferrocene Dipeptides with Hydrophobic Amino Acids. Inorganics, 11 (1). ISSN 2304-6740

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Despite the large number of peptidomimetics with incorporated heteroannularly functionalized ferrocenes, few studies have investigated their bioactivity. Here, we report the biological evaluation and conformational analysis of enantiomeric dipeptides derived from 1′- aminoferrocene- 1-carboxylic acid (Fca) and hydrophobic amino acids (AA = Val, Leu, Phe). The conformational properties of Y-AA-Fca-OMe (Y = Ac, Boc) were elucidated by experimental (IR, NMR, CD, and Xray) and theoretical (DFT) methods. The prepared dipeptides were screened for their antimicrobial activity against selected Gram- positive and Gram-negative bacteria, lactic acid bacteria and yeasts, while their antioxidant activity was tested by DPPH and FRAP methods. Of all compounds tested, dipeptide D-2a showed the best antibacterial properties against S. aureus, B. subtilis, and P. aeruginosa at a concentration of 2 mM. The time–kill curves showed that antibacterial activity was concentration- and time-dependent. Chirality (D-) and a more polar- protecting group (Ac) were found to affect the biological activity, both antimicrobial and antioxidant. All investigated peptides are considered to be highly hydrophobic and chemically stable in both acidic and buffer media. Dipeptides D-1a–3a, which showed biological activity, were subjected to the determination of proteolytic activity, revealing very good resistance to proteolysis in the presence of chymotrypsin.

Item Type: Article
Uncontrolled Keywords: Antimicrobial activity ; Antioxidant activity ; Proteolytic activity ; Chymotrypsin ; Hydrophobicity ; Peptidomimetics ; Conformational analysis ; Crystal structure ; Density Functional Theory (DFT) ; Hydrogen bonds
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
NMR Center
Project titleProject leaderProject codeProject type
Ferocenski analozi biomolekula: strukturna karakterizacija i biološka evaluacijaBarišić, LidijaIP-2020-02-9162HRZZ
Depositing User: Sunčica Roca
Date Deposited: 14 Apr 2023 12:30
DOI: 10.3390/inorganics11010029

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