57294-89-0Relevant academic research and scientific papers
Development of a Visible Light Triggerable Traceless Staudinger Ligation Reagent
Hu, Peng,Berning, Karsten,Lam, Yun-Wah,Ng, Isabel Hei-Ma,Yeung, Chi-Chung,Lam, Michael Hon-Wah
, p. 12998 - 13010 (2018/11/20)
A series of substituted 9-methylenylanthracene photocages for diphenylphosphinothioesters have been synthesized to explore their photo-uncaging properties by visible light. Substituents such as phenyl, p-trifluoromethylphenyl, p-methoxyphenyl, ethyn-1-ylbenzene, and 3,3-dimethylbut-1-yn-1-yl have been introduced in order to extend the π-conjugation of the photocage and to shift the wavelength response of the uncaging process to the visible spectral range. Among these new photocages, the (10-(3,3-dimethylbut-1-yn-1-yl)anthracen-9-yl)methyl has been shown to have the best performance in terms of fast photo-uncaging and minimal byproduct formation. It is responsive to both UV and visible photoexcitation. Quantum yields of the photoinduced heterolytic anthracenylmethyl-phosphorus bond cleavage at 366 and 416 nm were found to be 0.08 and 0.025, respectively. This photocage enables traceless Staudinger ligation to be triggered by photoirradiation in the visible spectral range for bioconjugation applications. We demonstrate this with a series of visible-light-induced oligopeptide syntheses via the conjugation of amino acid/oligopeptide building blocks by the characteristic peptide linkage attained by traceless Staudinger ligation. Yields of the resultant conjugated oligopeptides ranged from 31 to 43%. This new photocage opens up the possibility of in situ synthesis of functional proteins/peptides mediated by visible-light-induced photoclick processes for the regulation of cellular/metabolic functions of life systems.
1,2,3-TRIAZOLE-BASED PEPTIDOMIMETIC INTEGRIN INHIBITORS FOR THE DIAGNOSIS AND THERAPY OF TUMORS
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Page/Page column 25, (2011/09/15)
The present invention refers to the field of chemical compounds bearing a 1,2,3-triazole ring of formula (I) and possessing guanidino and carboxylic groups or their isosteres, their preparation by Cu-catalyzed "click-chemistry", and medical - diagnostic use in pathologies where angiogenesis is altered, for example pathologic conditions of tumor origin, tumor metastasis, osteoporosis, and rheumatoid arthritis.
Towards peptide-substituted titanocene anticancer drugs
Zagermann, Johannes,Deally, Anthony,Metzler-Nolte, Nils,Mueller-Bunz, Helge,Wallis, Denise,Tacke, Matthias
experimental part, p. 2387 - 2390 (2011/10/10)
An alkyne-substituted fulvene was transformed via hydridolithiation followed by transmetallation with titanium tetrachloride into bis-[p-(prop-2-ynyloxy)-benzyl-cyclopentadienyl] titanium(IV) dichloride. Single crystals of this titanocene derivative could be obtained and the structure determined by X-ray diffraction. It showed that this compound crystallises in the space group C2/c with four molecules in the monoclinic cell. The alkyne-substituted titanocene dichloride derivative was then subject to a copper-catalysed azide-alkyne cycloaddition with its azide-functionalised methylester-protected phenylalanine reaction partner in order to form a linking triazole. This reaction was performed under anhydrous conditions employing a dichloromethane/acetonitrile solvent mixture with copper(I) iodide and 2,6-lutidine as the catalyst system. Under these conditions the adduct between the protein mimic and the titanocene was formed without hydrolysing the titanium dichloride moiety.
Click-chemistry-derived triazole ligands of arginine-glycine-aspartate (RGD) integrins with a broad capacity to inhibit adhesion of melanoma cells and both in vitro and in vivo angiogenesis
Trabocchi, Andrea,Menchi, Gloria,Cini, Nicoletta,Bianchini, Francesca,Raspanti, Silvia,Bottoncetti, Anna,Pupi, Alberto,Calorini, Lido,Guarna, Antonio
supporting information; experimental part, p. 7119 - 7128 (2010/11/18)
A click chemistry approach was applied for the discovery of triazole-based arginine-glycine-aspartate (RGD) mimetics by Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction, which showed binding affinity properties toward αvβ3/αvβ5 integrins. Biological assays showed compound 18 capable of binding αvβ3 integrin with nanomolar affinity according to a two-sites model, and molecular modeling studies revealed a peculiar π-stacking interaction between the triazole ring and Tyr178 side chain. Accordingly, compound 18 inhibited the adhesion of integrin-expressing human melanoma cells to RGD-containing proteins of the extracellular matrix, such as vitronectin, fibronectin, and osteopontin, and also angiogenesis in in vitro and in vivo experimental models. The relevant biological effects exerted by compound 18 suggest its potential application as an antiangiogenic agent in the diagnosis and therapy of tumors where αvβ3 integrin expression is up-regulated.
Click chemistry inspired synthesis of novel ferrocenyl-substituted amino acids or peptides
Sudhir, V. Sai,Venkateswarlu,Musthafa, O. T. Muhammed,Sampath,Chandrasekaran, Srinivasan
body text, p. 2120 - 2129 (2009/09/06)
This work reports on the synthesis of a wide range of ferro- cenyl-substituted amino acids and peptides in excellent yield. Conjugation is established via copper-catalyzed 1,3- dipolar cycloaddition. Two complementary strategies were employed for conjugation, one involving cycloaddition of amino acid derived azides with ethynyl ferrocene 1 and the other involves cycloaddition between amino acid derived al- kynes with ferrocene-derived azides 2 and 3. Labeling of amino acids at multiple sites with ferrocene is discussed. A new route to 1,1'-unsymmetrically substituted ferrocene conjugates is reported. A novel ferrocenophane 19 is accessed via bimolecular condensation of amino acid derived bis- alkyne 9b with the azide 2. The electrochemical behavior of some selected ferrocene conjugates has been studied by cyclic voltammetry.
Chemoselective formation of successive triazole linkages in one pot: "Click-click" chemistry
Aucagne, Vincent,Leigh, David A.
, p. 4505 - 4507 (2007/10/03)
A methodology for the successive regiospecific "clicking" together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyne-azide cycloaddition reactions combined with a silver(I)-catalyzed TMS-
