Adamantyl ferrocene derivatives: Antioxidant abilities and effects on model lipid membranes

被引:4
作者
Stimac, Adela [1 ]
Lapic, Jasmina [2 ]
Blasina, Valentino [2 ]
Lukinac, Marija [2 ]
Djakovic, Senka [2 ]
Crnolatac, Ivo [3 ]
Frkanec, Leo [4 ]
Frkanec, Ruza [1 ]
机构
[1] Univ Zagreb, Ctr Res & Knowledge Transfer Biotechnol, Rockefellerova 10, Zagreb 10000, Croatia
[2] Univ Zagreb, Fac Food Technol & Biotechnol, Pierottijeva 6, Zagreb 610000, Croatia
[3] Rudjer Boskovic Inst, Div Organ Chem & Biochem, Lab Biomol Interact & Spect, Bijenicka 54, Zagreb 10000, Croatia
[4] Rudjer Boskovic Inst, Div Organ Chem & Biochem, Lab Supramol Chem, Bijenicka 54, Zagreb 10000, Croatia
关键词
adamantyl ferrocene; anisotropy; antioxidants; DSC; fluorescence; liposomes; membrane fluidity; MEDICINAL CHEMISTRY; AMANTADINE; LIPOSOMES; FLUIDITY; ADAMANTYLTRIPEPTIDES; LOCALIZATION; PEROXIDATION; RIMANTADINE; TOCOPHEROL; TRANSPORT;
D O I
10.1002/aoc.4042
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of homoannularly and heteroannularly substituted adamantyl ferrocene derivatives has been synthesized and their effects on membrane fluidity were investigated using liposomes as the membrane models. The liposome formulations of adamantyl ferrocene derivatives were characterized by using dynamic light scattering, differential scanning calorimetry and fluorescence anisotropy measurements. It was demonstrated that adamantyl ferrocene derivatives incorporated into the liposome significantly affect the structure of the lipid bilayer. The results of the study have revealed that adamantyl ferrocene derivatives, compounds 9-12, partition into the hydrophobic/hydrophilic interface of the membrane, causing a significant decrease in membrane fluidity. The antioxidant potential of synthesized compounds was assessed with DPPH method and it was shown that the examined compounds possess certain antioxidant activity.
引用
收藏
页数:14
相关论文
共 77 条
[41]   Potential Applications of Ferrocene as a Structural Feature in Antioxidants [J].
Liu, Zai-Qun .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2011, 11 (04) :345-358
[42]   Resveratrol induces chain interdigitation in DPPC cell membrane model systems [J].
Longo, Elena ;
Ciuchi, Federica ;
Guzzi, Rita ;
Rizzuti, Bruno ;
Bartucci, Rosa .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2016, 148 :615-621
[43]   Influence of some anti-inflammatory drugs in membrane fluidity studied by fluorescence anisotropy measurements [J].
Lúcio, M ;
Ferreira, H ;
Lima, JLFC ;
Matos, C ;
de Castro, B ;
Reis, S .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2004, 6 (07) :1493-1498
[44]  
Mansoori GA, 2007, ADV CHEM PHYS, V136, P207
[45]  
Mavromoustakos T. M., 2006, METHODS MOL BIOL MET, P400
[46]   Electrochemical analysis of the interactions and reactivity of ferrocene-based drugs with a lipid environment: A qualitative overview [J].
Mertins, O. ;
Messina, P. ;
Labbe, E. ;
Vivier, V. ;
Arbault, S. ;
Lemaitre, F. ;
Buriez, O. ;
Amatore, C. .
INORGANICA CHIMICA ACTA, 2011, 374 (01) :59-68
[47]   SYNTHESIS, CHARACTERIZATION AND CYTOTOXIC PROPERTIES OF THE 1ST METALLOCENONUCLEOSIDES [J].
MEUNIER, P ;
OUATTARA, I ;
GAUTHERON, B ;
TIROUFLET, J ;
CAMBOLI, D ;
BESANCON, J .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1991, 26 (03) :351-362
[48]   Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties [J].
Milaeva, E. R. ;
Filimonova, S. I. ;
Meleshonkova, N. N. ;
Dubova, L. G. ;
Shevtsova, E. F. ;
Bachurin, S. O. ;
Zefirov, N. S. .
BIOINORGANIC CHEMISTRY AND APPLICATIONS, 2010, 2010
[49]   New insights into water-phospholipid model membrane interactions [J].
Milhaud, J .
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 2004, 1663 (1-2) :19-51
[50]   ORGANIC AND ORGANOMETALLIC MOLECULAR MAGNETIC-MATERIALS - DESIGNER MAGNETS [J].
MILLER, JS ;
EPSTEIN, AJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04) :385-415