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Synthesis 2010(7): 1150-1158
DOI: 10.1055/s-0029-1218654
DOI: 10.1055/s-0029-1218654
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Bifunctional Hydroxamic Acids as Novel Ligands for the Hydrophilic Stabilization of Iron Oxide Nanoparticles
Further Information
Received
12 August 2009
Publication Date:
29 January 2010 (online)
Publication History
Publication Date:
29 January 2010 (online)
Abstract
A general method for synthesizing bifunctional hydroxamic acids containing carboxylic acid or amino functionalities is reported. Various products from simple alkyl to complex dendrimer-like structures are described. Such molecules have recently been used in ligand-exchange reactions for the hydrophilic stabilization of originally oleic acid protected iron oxide nanoparticles.
Key words
protecting groups - hydroxamic acids - hydrogenation - ethers - alkylations
- 1
Reddy AS.Kumar MS.Reddy GR. Tetrahedron Lett. 2000, 41: 6285 - 2
Kurzak B.Kozlowski H.Farkas E. Coord. Chem. Rev. 1992, 114: 169 - 3
Folkers JP.Gorman CB.Laibinis PE.Buchholz S.Whitesides GM. Langmuir 1995, 11: 813 - 4 As an example the complex formation
constant for acetohydroxamate with Fe(III) in aqueous solution is
2.6 × 10¹¹ mol-¹.
The corresponding value for acetate is only 2.4 × 10³ mol-¹:
Woo K.Lee HJ.Ahn JP.Park YS. Adv. Mater. 2003, 15: 1761 - 5
Emery T. Iron and Your Health: Facts and Fallacies CRC; Boca Raton / FL: 1991. p.15-17 - 6
Kim M.Chen Y.Liu Y.Peng X. Adv. Mater. 2005, 17: 1429 - 7
Park J.An K.Hwang Y.Park J.-G.Noh H.-J.Kim J.-Y.Park J.-H.Hwang N.-M.Hyeon T. Nature Mater. 2004, 3: 891 - 8
Jordan A.Maier-Hauff K.Wust P.Johannsen M. In Nanomaterials for Cancer TherapyChalla K. Wiley-VCH; Weinheim: 2006. p.242-258 - 9
Högemann D.Basilion JP.Weissleder R. Radiologe 2001, 41: 16 - 10
Jain TK.Richey J.Strand M.Leslie-Pelecky DL.Flask CA.Labhasetwar V. Biomaterials 2008, 29: 4012 - 12
Liénard BMR.Horsfall LE.Galleni M.Frère J.-M.Schofield CJ. Bioorg. Med. Chem. Lett. 2007, 17: 964 - 13
Bauer L.Exner O. Angew. Chem. 1974, 86: 419 - 14
Nagaoka Y.Maeda T.Kawai Y.Nakashima D.Oikawa T.Shimoke K.Ikeuchi T.Kuwajima H.Uesato S. Eur. J. Med. Chem. 2006, 41: 697 - 15
Guo W.Li J.Wang YA.Peng X. J. Am. Chem. Soc. 2003, 125: 3901 - 16
Wang YA.Li JJ.Chen H.Peng X. J. Am. Chem. Soc. 2002, 124: 2293 - 17
Niwa M.Morikawa M.Nabeta T.Higashi N. Macromolecules 2002, 35: 2769 - 18
McKenna MD.Barberá J.Marcos M.Serrano JL. J. Am. Chem. Soc. 2005, 127: 619 - 19
Selve C.Ravey J.-C.Stebe M.-J.El Moudjahid C.Moumni EM.Delpuech J.-J. Tetrahedron 1991, 47: 411 - 20
Ramsay SL.Freeman C.Grace PB.Redmond JW.MacLeod JK. Carbohydrate Res. 2001, 333: 59 - 21
McKenna M.Barbera J.Marcos M.Serrano JL. J. Am. Chem. Soc. 2005, 127: 619 - 22
Zhu J.Beugelmans R.Bourdet S.Chastanet J.Roussi G. J. Org. Chem. 1995, 60: 6389 - 23
Koushik M.Joyeeta S.Arabinda C. FEBS Lett. 2005, 579: 1291 - 24
Brouwer AJ.Liskamp RMJ. Eur. J. Org. Chem. 2005, 487 - 25
Brouwer AJ.Mulders SJE.Liskamp RMJ. Eur. J. Org. Chem. 2001, 1903 - 26
Freitas JM.Abrantes LM.Darbre T. Helv. Chim. Acta 2005, 88: 2470
References
Hofmann, A.; Graf, C.; Semisch, A.; Hartwig, A.; Rühl, E. manuscript in preparation.