129952-31-4Relevant articles and documents
A dansyl-derivatized phytic acid analogue as a fluorescent substrate for phytases: experimental and computational approach
Dussouy, Christophe,Dubreucq, Eric,Chemardin, Patrick,Perrier, Véronique,Abadie, Josiane,Quiquampoix, Hervé,Plassard, Claude,Behr, Jean-Bernard
, (2021)
A new myo-inositol pentakisphosphate was synthesized, which featured a dansyl group at position C-5. The fluorescent tag was removed from the inositol by a 6-atom spacer to prevent detrimental steric interactions in the catalytic site of phytases. The PEG linker was used in order to enhance hydrophilicity and biocompatibility of the new artificial substrate. Computational studies showed a favorable positioning in the catalytic site of phytases. Enzymatic assays demonstrated that the tethered myo-inositol was processed by two recombinant phytases Phy-A and Phy-C, classified respectively as acid and alkaline phytases, with similar rates of phosphate release compared to their natural substrate.
Synthesis and screening of novel inositol phosphonate derivatives for anticancer functions in vitro
Chen, Wen-Bin,Liu, Jian-Bing,Dou, Dao-Lei,Song, Fan-Bo,Li, Lu-Yuan,Xi, Zhen
, p. 329 - 333 (2015/04/14)
Phosphonates have been frequently used as suitable isosteric and isoelectronic replacements for biologically important phosphates in the development of drugs or drug candidates because of their stability toward the action of phosphatases and other enzymes. In this paper, 12 mono-phosphonate inositol compounds were prepared with phosphonate instead of phosphate by two kinds of strategies, nucleophilic substitution and Arbuzov rearrangement, respectively. All compounds were evaluated in vitro for their activity against non-small cell lung cancer (NSCLC) cell line A549. Two compounds (3ac and 3bb) exhibited good antitumor activity at 10 μg/mL.
Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
, p. 172 - 181 (2015/03/05)
The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo
Synthesis and antitumor activity of inositol phosphotriester analogues
Song, Fanbo,Zhang, Jing,Zhao, Yuefang,Chen, Wenbin,Li, Luyuan,Xi, Zhen
experimental part, p. 3642 - 3654 (2012/06/18)
Inositol phosphates, as important second messengers of signal transduction, regulate many biological functions. However, cell penetration and phospholipase stability could be two main issues faced by inositol phosphate analogues used as lead compounds for drug discovery. Inositol phosphotriester analogues could be more beneficial to diffuse across plasma membrane. In this paper, we describe the design and synthesis of a series of inositol phosphotriester analogues based on phosphatidylinositol, along with the initial antitumor activity analysis. Several compounds exhibited good cytotoxic activity against human cancer cell lines A549, HepG2, MDA-MB-231 and HeLa, especially compound 33 was cytotoxic against all the four cancer cell lines with good IC50 values.
A short and efficient route from myo - To neo -inositol
Wessig, Pablo,M?llnitz, Kristian,Hübner, Sebastian
scheme or table, p. 1497 - 1500 (2010/09/05)
An efficient route from myo- to neo-inositol is described. The key steps of the sequence are oxidation of the hydroxy group at C-5 to the corresponding ketone, followed by a highly (dr = 7.8:1) stereoselective reduction. The route includes nine steps with an overall yield of 51% and is therefore superior to all hitherto reported methods for the preparation of neo-inositol. Georg Thieme Verlag Stuttgart New York.
Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
Conway, Stuart J.,Gardiner, James,Grove, Simon J. A.,Johns, Melloney K.,Lim, Ze-Yi,Painter, Gavin F.,Robinson, Diane E. J. E.,Schieber, Christine,Thuring, Jan W.,Wong, Leon S.-M.,Yin, Meng-Xin,Burgess, Antony W.,Catimel, Bruno,Hawkins, Phillip T.,Ktistakis, Nicholas T.,Stephens, Leonard R.,Holmes, Andrew B.
scheme or table, p. 66 - 76 (2010/04/29)
The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A-E is described. These core compounds were obtained from myo-inositol orthoformate 1 via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution-protection process using camphor acetals 10. Coupling of cores A-E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins. The Royal Society of Chemistry 2010.
General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives
Painter, Gavin F.,Grove, Simon J. A.,Gilbert, Lan H.,Holmes, Andrew B.,Raithby, Paul R.,Hill, Malcolm L.,Hawking, Phillip T.,Stephens, Leonard R.
, p. 923 - 935 (2007/10/03)
The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.
Lewis acid-catalysed rearrangement of myo-inositol orthoformate derivatives
Gilbert, Ian H.,Holmes, Andrew B.,Pestchanker, Mauricio J.,Young, Rodney C.
, p. 117 - 130 (2007/10/02)
Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) with di-isobutylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-
SYNTHESIS OF PROTECTED myo-INOSITOLS
Gilbert, Ian H.,Holmes, Andrew B.,Young, Rodney C.
, p. 2633 - 2634 (2007/10/02)
Regioselective cleavages of the myo-inositol monoorthoformate (2) and a rearrangement of the acetal (5) are reported.
