Synthesis and evaluation of a novel lipid-peptide conjugate for functionalized liposome

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 9, 2007, Pages 2590-2593

  Yagi, Nobuhiro ^a   Yano, Yuko ^a   Hatanaka, Kentaro ^a   Yokoyama, Yuusaku ^a   Okuno, Hiroaki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Cellular uptake; Functional liposome; Lipopeptide; TAT peptide

Indexed keywords

AMINO ACID DERIVATIVE; FATTY ACID DERIVATIVE; LIPOPEPTIDE; LIPOSOME; RESIN; TRANSACTIVATOR PROTEIN;

ANIMAL CELL; ARTICLE; CONJUGATE; CONJUGATION; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; LIPID BILAYER; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID;

ANIMALS; CERCOPITHECUS AETHIOPS; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COS CELLS; DRUG DESIGN; FATTY ACIDS; GENE PRODUCTS, TAT; LIPIDS; LIPOSOMES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PEPTIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

HUMAN IMMUNODEFICIENCY VIRUS;

EID: 33947716252     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.02.001     Document Type: Article

References (14)

1. Krown S., Northfelt D., Osoba D., and Stewart J. Semin. oncol. 31 (2004) 36
2. Iyer A.K., Khaled G., Fang J., and Maeda H. Drug Discovery Today 11 (2006) 812
3. Allen T.M. Nat. Rev. Cancer 2 (2002) 750
4. Khalil I.A., Kogure K., Futaki S., and Harashima H. J. Biol. Chem. 281 (2006) 3544
5. Oku N., Asai T., Watanabe K., Kuromi K., Nagatsuka M., Kurohane K., Kikkawa H., Ogino K., Tanaka M., Ishikawa D., Tsukada H., Momose M., Nakayama J., and Taki T. Oncogene 21 (2002) 2662
6. Gregoriadis G., Florence A., and Patel H. Liposome in Drug Delivery (1993), Harwood Academic Publishers, NJ pp 227-238
7. Green M., and Loewenstein P.M. Cell 55 (1998) 1179
8. Torchilin V.P. Ann. Rev. Biomed. Eng. 8 (2006) 343
9. Torchilin V.P., Levchenko T.S., Rammohan R., Volodina N., Papahadjopoulous-Sternberg B., and D'Souza G.G. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 1972
10. Fretz M.M., Koning G.A., Mastrobattista E., Jiskoot W., and Storm G. Biochim. Biophys. Acta 1665 (2004) 48
11. Koskinen A.M.P., Valo T., Vihavainen S., and Hakala J.M.L. Bioorg. Med. Chem. Lett. 5 (1995) 573
12. 3CN from 100:0 to 0:100; Detection, 280 nm; Flow rate, 1.0 mL/min.
13. MALDI-TOFMS of 1 was performed in linear mode at 20k acceleration voltage using sinapic acid as matrix. For ionization, a nitrogen laser (337 nm, 0.5 ns pulse width, 3 Hz, 25 times/spectrum) was used. All spectra were measured using external calibration.
14. The undesired side products were resulted with C18 simply due to their solubility differences in DMF during the condensation reaction.