A novel steroidal spin label for membrane structure studies: synthesis and applications

• Published in: Steroids Vol. 64; no. 12; pp. 849 - 855
• Main Authors: Katoch, Rita, Trivedia, Girish K., Phadke, Ratna S.
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier Inc 01.12.1999; Elsevier; Elsevier Science
• Subjects: 1,2-Dipalmitoylphosphatidylcholine - chemistry; 3α-hydroxycholan-24-yl-(2″,2″,6″,6″-tetramethyl- N-oxyl)piperidyl butan-1′,4′-dioate; Alicyclic compounds, terpenoids, prostaglandins, steroids; Biochemistry & Molecular Biology; Chemistry; Electron Spin Resonance Spectroscopy; Endocrinology & Metabolism; Exact sciences and technology; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Mass Spectrometry; Membranes, Artificial; Model membrane; Molecular Structure; Organic chemistry; Phase transition; Preparations and properties; Science & Technology; Spectrophotometry, Infrared; Spin label; Spin Labels - chemical synthesis; Steroids; TEMPO nitroxyl; TEMPO nitroxyl; 3α-hydroxycholan-24-yl-(2″,2″,6″,6″-tetramethyl- N-oxyl)piperidyl butan-1′,4′-dioate; Model membrane; Spin label; Phase transition; MODEL MEMBRANES; NITROXIDES; 2'-(3-ALPHA-BENZYLOXY-24-NORCHOLAN-23-YL)-2',4',4'-TRIMETHYL-4',5'-DIHYDROOXAZO; spin label; CHEMISTRY; 3 alpha-hydroxycholan-24-yl(2 '',2 '',6 '',6 ''-tetramethyl-N-oxyl)piperdyl butan-1 ',4 '-dioate; LITHOCHOLIC ACID; model membrane; PROBE; BIOMEMBRANES; Epinephrine; Spin labelling; Steroid; Nitroxyl; Organic free radical; Bile acid; Model compound; Saturated compound; Biomembrane; Permeability; Chemical synthesis; Phase transitions
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/S0039-128X(99)00072-0

2,2,6,6-Tetramethyl piperidine- N-oxyl nitroxyls are known to partition between aqueous and lipid phases, thus serving as probes to study membrane dynamics. The synthesis of a novel steroidal spin label, 3α-hydroxycholan-24-yl-(2″,2″,6″,6″-tetramethyl- N-oxyl)piperidyl butan-1′,4′-dioate, containing 2,2,6,6-tetramethylpiperidine- N-oxyl moiety covalently bonded to the side chain in 3,24-caprostan-diol has been described. The localization of this spin label in model biomembranes has been studied by using electron spin resonance, differential scanning calorimetry, and 1H and 31P NMR spectroscopic techniques. Its applicability in studying the phase transition properties of model membrane l-α-dipalmitoyl phosphatidyl choline in the presence and absence of drugs has been described by using electron spin resonance. The label has also been used to study the permeability of epinephrine into membrane. The results have shown the applicability of the spin label as a potential spin probe in the study of biomembranes.