Synthesis and biological activity of M6-P and M6-P analogs on fibroblast and keratinocyte proliferation

Farmaco

Volumn 60, Issue 9, 2005, Pages 721-725

  Clavel, Caroline ^a   Barragan Montero, Véronique ^a   Garric, Xavier ^b   Molès, Jean Pierre ^b   Montero, Jean Louis ^a  

^a CNRS   (France)

^b UNIV MONTPELLIER   (France)

Author keywords

Mannose 6 phosphate; Mannose 6 phosphate analogs; Mitsunobu; Proliferation; Skin

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DRUG ANALOG; MANNOSE 6 PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; SODIUM (METHYL 6,7 DIDEOXY ALPHA DEXTRO MANNOOCTOPYRANOSIDE)URONATE; UNCLASSIFIED DRUG;

ARTICLE; CELL LINE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; DRUG POTENCY; DRUG SYNTHESIS; FIBROBLAST; HUMAN; HUMAN CELL; KERATINOCYTE; SKIN FIBROBLAST;

3T3 CELLS; ANIMALS; CELL PROLIFERATION; FIBROBLASTS; KERATINOCYTES; MANNOSEPHOSPHATES; MICE;

EID: 24944488026     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2005.06.006     Document Type: Article

References (32)

1. N.M. Dahms, and M.K. Hancock P-type lectins Biochim. Biophys. Acta 1572 2002 317 340
2. T. Braulke Type-2 IGF receptor: a multi-ligand binding protein Horm. Metab. Res. 31 1999 242 246
3. J.X. Kang, Y. Li, and A. Leaf Mannose-6-phosphate/insulin-like growth factor-II receptor is a receptor for retinoic acid Proc. Natl. Acad. Sci. USA 94 1997 13671 13676
4. J.X. Kang, J. Bell, R.L. Beard, and R.A. Chandraratna Mannose 6-phosphate/insulin-like growth factor II receptor mediates the growth-inhibitory effects of retinoids Cell Growth Differ. 10 1999 591 600
5. A. Nykjaer, E.I. Christensen, H. Vorum, H. Hager, C.M. Petersen, H. Roigaard, H.Y. Min, F. Vilhardt, L.B. Moller, S. Kornfeld, and J. Gliemann Mannose 6-phosphate/insulin-like growth factor-II receptor targets the urokinase receptor to lysosomes via a novel binding interaction J. Cell Biol. 141 1998 815 828
6. S. Godar, V. Horejsi, U.H. Weidle, B.R. Binder, C. Hansmann, and H. Stockinger M6P/IGFII-receptor complexes urokinase receptor and plasminogen for activation of transforming growth factor-beta1 Eur. J. Immunol. 29 1999 1004 1013
7. P.A. Dennis, and D.B. Rifkin Cellular activation of latent transforming growth factor beta requires binding to the cation-independent mannose 6-phosphate/insulin-like growth factor type II receptor Proc. Natl. Acad. Sci. USA 88 1991 580 584
8. A. Ghahary, E.E. Tredget, and Q. Shen Insulin-like growth factor-II/mannose 6-phosphate receptors facilitate the matrix effects of latent transforming growth factor-beta1 released from genetically modified keratinocytes in a fibroblast/keratinocyte co-culture system J. Cell Physiol. 180 1999 61 70
9. C. Raf The Molecular and Cellular Biology of Wound Repair R.A.F. Clark 1996 Plenum New-York
10. P. Martin Wound healing: aiming for perfect skin regeneration Science 276 1997 75 81
11. 1,2 reduces cutaneous scarring in adult rodents J. Cell Sci. 107 1994 1137 1157
12. 3 to cutaneous rat wounds reduces scarring J. Cell Sci. 108 1995 985 1002
13. J.S. Huang, Y.-H. Wang, T.-Y. Ling, S.-S. Chuang, F.E. Johnson, and S.S. Huang Synthetic TGF-β antagonist accelerates wound healing and reduces scarring, FASEB J 16 2002 1269 1270
14. C. Vidil, A. Mor̀re, M. Garcia, V. Barragan, B. Hamdaoui, H. Rochefort, and J.-L. Montero Synthesis and biological activity of phosphonate analogs of mannose 6-phosphate (M6P) Eur. J. Org. Chem. 2 1999 447 450
15. S. Vidal, M. Garcia, J.-L. Montero, and A. Morere Synthesis and biological evaluation of new mannose 6-phosphate analogs Bioorg. Med. Chem. 10 2002 4051 4056
16. H.B. Boŕn, K. Eklind, P.J. Garegg, B. Lindberg, and A. Pilotti Synthesis of 6-deoxy-d-manno-heptose Acta Chem. Scand. A 26 1972 4143 4146
17. K. Omura, and D. Swern Oxidation of alcohols by "activated" dimethyl sulfoxide. A preparative steric and mechanistic study Tetrahedron 34 1978 1651 1660
18. A.J. Mancuso, S.-L. Huan, and D. Swern Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride J. Org. Chem. 43 1978 2480 2482
19. J. Boutagy, and R. Thomas Olefin synthesis with organic phosphonate carbanions Chem. Rev. 74 1974 87 99
20. B.E. Maryanoff, and A.B. Reitz The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects Chem. Rev. 89 1989 863 927
21. J.M. Takacs, Z. Xu, X.-T. Jiang, A.P. Leonov, and G.C. Theriot Carbon nucleophiles in the Mitsunobu reaction. Mono- and dialkylation of bis(2,2,2-trifluoroethyl) malonates Org. Lett. 4 2002 3843 3845
22. C. Clavel, V. Barragan-Montero, and J.-L. Montero Chain elongation of primary alcohols of carbohydrates Tetrahedron Lett. 45 2004 7465 7467
23. +.
24. J.G. Rheinwald, and H. Green Serial cultivation of strains of human epidermal keratinocytes: the formation of keratinizing colonies from single cells Cell 6 1975 331 343
25. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
26. M.B. Hansen, S.E. Nielsen, and K. Berg Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill J. Immunol. Methods 11 1989 203 210
27. K. von Figura, V. Gieselmann, and A. Hasilik Antibody to mannose 6-phosphate specific receptor induces receptor deficiency in human fibroblasts EMBO J. 3 1984 1281 1286
28. H.N. Antoniades, T. Galanopoulos, J. Neville-Golden, C.P. Kiritsy, and S.E. Lynch Expression of growth factor and receptor mRNAs in skin epithelial cells following acute cutaneous injury Am. J. Pathol. 142 1993 1099 1110
29. C. Lenoir, A. Dace, C. Martin, J. Bonne, M. Teboul, R. Planells, and J. Torresani Calcitriol down-modulates the 3,5,3′ triiodothyronine (T3) receptors and affects, in a biphasic manner, the T3-dependent adipose differentiation of Ob 17 preadipocytes Endocrinology 137 1996 4268 4276
30. A.B. Roberts, A. Russo, A. Felici, and K.C. Flanders Smad3: a key player in pathogenetic mechanisms dependent on TGF-β Ann. New York Acad. Sci. 995 2003 1 10
31. W. Xia, T.-T. Phan, I.J. Lim, M.T. Longaker, and G.P. Yang Complex epithelial-mesenchymal interactions modulates transforming growth factor-β expression in keloid-derived cells Wound Rep. Reg. 12 2004 546 556
32. W. Liu, D.R. Wang, and Y.L. Cao TGF-β: a fibrotic factor in wound scarring and a potential target for anti-scarring gene therapy Curr. Gene Ther. 4 2004 123 136