点击化学在新型多价 RGD 缀合物合成中的应用。
Application of click-click chemistry to the synthesis of new multivalent RGD conjugates.
机构信息
Département de Chimie Moléculaire, UMR CNRS/UJF 5250, ICMG FR 2607, 570 rue de la chimie, BP 53, 38041 Grenoble cedex 9, France.
出版信息
Org Biomol Chem. 2010 Nov 21;8(22):5133-8. doi: 10.1039/c0ob00070a. Epub 2010 Sep 9.
Abstract
New multivalent RGD-containing macromolecules were designed by exploiting two orthogonal chemoselective ligations. They were next applied to a competitive cell adhesion assay and used for the non invasive optical imaging of tumour in small animals.
摘要
新的多价含有 RGD 的大分子通过利用两种正交的化学选择性连接方法来设计。然后将它们应用于竞争性细胞黏附测定，并用于小动物肿瘤的非侵入性光学成像。
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本文引用的文献
1
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2
Oligonucleotide sequential bis-conjugation via click-oxime and click-Huisgen procedures.通过点击肟和点击希夫基反应进行寡核苷酸顺序双连接。
J Org Chem. 2010 Jun 4;75(11):3927-30. doi: 10.1021/jo100599m.
3
Synthesis of multivalent glycoconjugates containing the immunoactive LELTE peptide: effect of glycosylation on cellular activation and natural killing by human peripheral blood mononuclear cells.合成含有免疫活性 LELTE 肽的多价糖缀合物：糖基化对人外周血单核细胞的细胞激活和自然杀伤的影响。
J Am Chem Soc. 2010 May 19;132(19):6800-8. doi: 10.1021/ja101296t.
4
Combined Cu(I)-catalysed alkyne-azide cycloaddition and furan-maleimide Diels-Alder "click" chemistry approach to thermoresponsive dendrimers.铜（I）催化的炔基-叠氮化物环加成反应和呋喃-马来酰亚胺 Diels-Alder“点击”化学方法合成热敏树枝状聚合物。
Chem Commun (Camb). 2010 Mar 21;46(11):1875-7. doi: 10.1039/b924888a. Epub 2010 Jan 13.
5
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Int J Pharm. 2009 Sep 11;379(2):309-16. doi: 10.1016/j.ijpharm.2009.05.034. Epub 2009 May 23.
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