Abstract
A conjugate between the cyclic peptide CNGRC and doxorubcin,
previously reported as a ligand of aminopeptidase N (CD13), has
been synthesised and characterised.
Key words
solid-phase synthesis - CNGRC - peptides - doxorubicin - angiogenesis - macrocycles - anti-tumour agents
References 1 Abbreviations: Acm, acetamidomethyl;
DIPEA, N,N -diisopropylethylamine; Fmoc,
9-fluorenylmethoxycarbonyl; HOBt, 1-hydroxybenzotriazole; Pbf, 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl;
PyBOP, benzotriazole-1-yloxytrispyrrolidinophosphonium hexafluorophosphate.
2 Present address: Synthèse
et Etude de Systèmes à Intéret Biologique,
Université Blaise Pascal, UMR 6504, 63177 Aubière,
France.
3
Risau W.
Nature
(London)
1997,
386:
671
4
Zetter BR.
Ann.
Rev. Med.
1998,
49:
407
5
Ruoslahti E.
Ann.
Rev. Cell Dev. Biol.
1996,
12:
697
6
Pasqualini R.
Koivunen E.
Ruoslahti E.
Nature Biotechnol.
1997,
15:
542
7
Haubner R.
Finsinger D.
Kessler H.
Angew.
Chem., Int. Ed. Engl.
1997,
36:
1375
8
Arap W.
Pasqualini R.
Ruoslahti E.
Science
1998,
279:
377
9
Koivunen E.
Gay DA.
Ruoslahti E.
J.
Biol. Chem.
1993,
268:
20205
10
Koivunen E.
Wang BC.
Ruoslahti E.
J.
Cell Biol.
1994,
124:
373
11
Healy JM.
Murayama O.
Maeda T.
Yoshino K.
Sekiguchi K.
Kikuchi M.
Biochemistry
1995,
34:
3948
12
Pasqualini R.
Koivunen E.
Kain R.
Lahdenranta J.
Sakamoto M.
Stryhn A.
Ashmun RA.
Shapiro LH.
Arap W.
Ruoslahti E.
Cancer Res.
2000,
60:
722
13
Ellerby HM.
Arap W.
Ellerby LM.
Kain R.
Andrusiak R.
DelRio G.
Krajewski S.
Lombardo CR.
Rao R.
Ruoslahti E.
Bredesen DE.
Pasqualini R.
Nature Medicine
1999,
5:
1032
14
Pons M.
Albericio F.
Royo M.
Giralt E.
Synlett
2000,
172
15
Veber DF.
Milkowski JD.
Varga SL.
Denkewalter RG.
Hirschmann R.
J. Am. Chem. Soc.
1972,
94:
5456
16
Carpino LA.
Shroff HN.
Triolo SA.
Mansour EMA.
Wenschuh H.
Albericio F.
Tetrahedron
Lett.
1993,
34:
7829