Interaction of acyclovir and its squalenoyl-acyclovir prodrug with DMPC in monolayers at the air/water interface.
作者： Maria Grazia Sarpietro , Flavio Rocco , Dorotea Micieli , Sara Ottimo , Maurizio Ceruti
DOI: 10.1016/J.IJPHARM.2010.05.035
关键词: Conjugated system 、 Moiety 、 Langmuir–Blodgett film 、 Combinatorial chemistry 、 Membrane 、 Stereochemistry 、 Phospholipid 、 Biological membrane 、 Monolayer 、 Chemistry 、 Prodrug
摘要: Abstract Acyclovir has been conjugated to the acyclic isoprenoid chain of squalene form squalenoyl–acyclovir prodrug. Its interaction with biomembrane models constituted by dimyristoylphosphatidylcholine (DMPC) monolayers studied employing Langmuir–Blodgett technique. The aim work was gain information on these compounds phospholipid membranes. DMPC/acyclovir or prodrug mixed have prepared at increasing molar fractions compound and isotherm mean molecular area/surface pressure registered 10 37 °C. Results reveal that squalenoyl moiety enhances affinity acyclovir for model.
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sci-hub.se 参考文章(23)
George L. Gaines, Insoluble Monolayers at Liquid-gas Interfaces ,(1966)
HIROATSU MATSUMOTO, CHISATO KANEKO, KEIKO YAMADA, TADAO TAKEUCHI, TAKEO MORI, YOSHIHISA MIZUNO, A convenient synthesis of 9-(2-hydroxyethoxymethyl)guanine (acyclovir) and related compounds. Chemical & Pharmaceutical Bulletin. ,vol. 36, pp. 1153- 1157 ,(1988) , 10.1248/CPB.36.1153
G. Chimote, R. Banerjee, Molecular interactions of cord factor with dipalmitoylphosphatidylcholine monolayers: implications for lung surfactant dysfunction in pulmonary tuberculosis. Colloids and Surfaces B: Biointerfaces. ,vol. 65, pp. 120- 125 ,(2008) , 10.1016/J.COLSURFB.2008.03.004
Gerald Brezesinski, Helmuth Möhwald, Langmuir monolayers to study interactions at model membrane surfaces Advances in Colloid and Interface Science. ,vol. 100, pp. 563- 584 ,(2003) , 10.1016/S0001-8686(02)00071-4
Francesco Castelli, Maria Grazia Sarpietro, Dorotea Micieli, Barbara Stella, Flavio Rocco, Luigi Cattel, Enhancement of gemcitabine affinity for biomembranes by conjugation with squalene: differential scanning calorimetry and Langmuir-Blodgett studies using biomembrane models. joint international conference on information sciences. ,vol. 316, pp. 43- 52 ,(2007) , 10.1016/J.JCIS.2007.07.064
C PERIGAUD, G GOSSELIN, J GIRARDET, B KORBA, J IMBACH, The S-acyl-2-thioethyl pronucleotide approach applied to acyclovir: part I. Synthesis and in vitro anti-hepatitis B virus activity of bis(S-acyl-2-thioethyl)phosphotriester derivatives of acyclovir. Antiviral Research. ,vol. 40, pp. 167- 178 ,(1999) , 10.1016/S0166-3542(98)00059-X
Dae-Kee Kim, Namkyu Lee, Guang-Jin Im, Hun-Taek Kim, Key H. Kim, SYNTHESIS AND EVALUATION OF 2-AMINO-6-FLUORO-9-(2-HYDROXYETHOXYMETHYL)PURINE ESTERS AS POTENTIAL PRODRUGS OF ACYCLOVIR Bioorganic & Medicinal Chemistry. ,vol. 6, pp. 2525- 2530 ,(1998) , 10.1016/S0968-0896(98)80026-6
Antona J. Wagstaff, Diana Faulds, Karen L. Goa, Aciclovir. A reappraisal of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. ,vol. 47, pp. 153- 205 ,(1994) , 10.2165/00003495-199447010-00009
N. Krasteva, D. Vollhardt, G. Brezesinski, Mixed Stearoyl-rac-glycerol/12-(Hydroxy)stearoyl-rac-glycerol Monolayers on the Air/Water Interface: Brewster Angle Microscopy and Grazing Incidence X-ray Diffraction Investigation Journal of Physical Chemistry B. ,vol. 104, pp. 8704- 8711 ,(2000) , 10.1021/JP001479K
Régine Maget-Dana, The monolayer technique: a potent tool for studying the interfacial properties of antimicrobial and membrane-lytic peptides and their interactions with lipid membranes. Biochimica et Biophysica Acta. ,vol. 1462, pp. 109- 140 ,(1999) , 10.1016/S0005-2736(99)00203-5