Synthesis and binding properties to DNA and to opioid receptors of enkephalin‐ellipticinium conjugates
作者： P. RIGAUDY , Ch. GARBAY-JAUREGUIBERRY , A. JACQUEMIN-SABLON , J-B. LE PECQ , B.P. ROQUES
DOI: 10.1111/J.1399-3011.1987.TB03341.X
关键词: DNA 、 Amino acid 、 Pentapeptide repeat 、 Biochemistry 、 Opioid receptor 、 Enkephalin 、 Chemistry 、 Stereochemistry 、 Tripeptide 、 Ellipticines 、 Receptor
摘要: In order to specifically direct cytotoxic agents against tumor cells bearing delta opioid receptors, the DNA intercalating ellipticine and 9-OH-ellipticine were coupled by quaternarization of pyridine nitrogen an enkephalin modified pentapeptide through a short chemical linker. The ring these conjugates was shown intercalate into DNA, with affinity constants close those non-conjugated ellipticines. Despite addition polycyclic C-terminal amino acid, D-Ala2-D-Leu5-enkephalin-ellipticine bind receptor from rat brain NG 108-15 constant 10(8) M-1. Other derivatives synthesized as control using tripeptide which does not receptor.
sci-hub.se 参考文章(27)
P Y Law, D S Hom, H H Loh, Down-regulation of opiate receptor in neuroblastoma x glioma NG108-15 hybrid cells. Chloroquine promotes accumulation of tritiated enkephalin in the lysosomes. Journal of Biological Chemistry. ,vol. 259, pp. 4096- 4104 ,(1984) , 10.1016/S0021-9258(17)43014-6
J.M. Saucier, B. Festy, J.-B. Le Pecq, The change of the torsion of the DNA helix caused by intercalation. II. Measurement of the relative change of torsion induced by various intercalating drugs. Biochimie. ,vol. 53, pp. 973- 980 ,(1971) , 10.1016/S0300-9084(71)80065-2
J.-B. Lepecq, C. Paoletti, A fluorescent complex between ethidium bromide and nucleic acids. Physical-chemical characterization. Journal of Molecular Biology. ,vol. 27, pp. 87- 106 ,(1967) , 10.1016/0022-2836(67)90353-1
S G Blanchard, K J Chang, P Cuatrecasas, Characterization of the association of tritiated enkephalin with neuroblastoma cells under conditions optimal for receptor down regulation. Journal of Biological Chemistry. ,vol. 258, pp. 1092- 1097 ,(1983) , 10.1016/S0021-9258(18)33163-6
A. Lewis Farr, Oliver H. Lowry, Rose J. Randall, Nira J. Rosebrough, Protein Measurement with the Folin Phenol Reagent Journal of Biological Chemistry. ,vol. 193, pp. 265- 275 ,(1951)
Bernard Maigret, Bernard P. Roques, Marie-Claude Fournie-Zaluski, Gilles Gacel, Samuel Premilat, Structural requirements for specific recognition of mu or delta opiate receptors. Molecular Pharmacology. ,vol. 20, pp. 484- 491 ,(1981)
W. Keller, Determination of the number of superhelical turns in simian virus 40 DNA by gel electrophoresis. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 72, pp. 4876- 4880 ,(1975) , 10.1073/PNAS.72.12.4876
Gilles Gacel, Marie Claude Fournie-Zaluski, Etienne Fellion, Bernard P. Roques, Evidence of the preferential involvement of mu receptors in analgesia using enkephalins highly selective for peripheral mu or delta receptors. Journal of Medicinal Chemistry. ,vol. 24, pp. 1119- 1124 ,(1981) , 10.1021/JM00142A002
T. BELSKY, R. B. JOHNS, E. D. McCARTHY, A. L. BURLINGAME, W. RICHTER, MELVIN CALVIN, Evidence of Life Processes in a Sediment Two and a Half Billion Years Old Nature. ,vol. 206, pp. 446- 447 ,(1965) , 10.1038/206446A0
James D. McGhee, Peter H. von Hippel, Theoretical aspects of DNA-protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. Journal of Molecular Biology. ,vol. 86, pp. 469- 489 ,(1974) , 10.1016/0022-2836(74)90031-X