Literature DB >> 23859776

Improved synthesis of 17β-hydroxy-16α-iodo-wortmannin, 17β-hydroxy-16α-iodoPX866, and the [(131)I] analogue as useful PET tracers for PI3-kinase.

Duoli Sun1, Basvoju A Bhanu Prasad, Paul T Schuber, Zhenghong Peng, David S Maxwell, Diana V Martin, Liwei Guo, Dongmei Han, Hiroaki Kurihara, David J Yang, Juri G Gelovani, Garth Powis, William G Bornmann.   

Abstract

An improved method for the synthesis of 17β-hydroxy-16α-iodo-wortmannin along with the first synthesis of 17β-hydroxy-16α-iodoPX866 and [(131)I] radiolabeled 17β-hydroxy-16α-[(131)I]iodo-wortmannin, as potential PET tracers for PI3K was also described. The differences between wortmannin and its iodo analogue were compared by covalently docking each structure to L833 in PI3K.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  17β-Hydroxy-16α-[(131)I]iodowortmannin; 17β-Hydroxy-16α-iodoPX866; 17β-Hydroxy-16α-iodowortmannin; LYDLNTRBZQFQTG-RUXBYQPCSA-N; OWEYHVVHIWKFGJ-TUYZGLGGSA-N; PI3 kinase; Positron emission tomography (PET) imaging

Mesh：

Substances：

Year:  2013        PMID： 23859776      PMCID： PMC3960976          DOI： 10.1016/j.bmc.2013.06.036

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  18 in total

Review 1.  PET as a potential tool for imaging molecular mechanisms of oncology in man.

Authors:  P Price
Journal:  Trends Mol Med       Date:  2001-10       Impact factor: 11.951

2.  High frequency of mutations of the PIK3CA gene in human cancers.

Authors:  Yardena Samuels; Zhenghe Wang; Alberto Bardelli; Natalie Silliman; Janine Ptak; Steve Szabo; Hai Yan; Adi Gazdar; Steven M Powell; Gregory J Riggins; James K V Willson; Sanford Markowitz; Kenneth W Kinzler; Bert Vogelstein; Victor E Velculescu
Journal:  Science       Date:  2004-03-11       Impact factor: 47.728

3.  Studies on the mechanism of phosphatidylinositol 3-kinase inhibition by wortmannin and related analogs.

Authors:  B H Norman; C Shih; J E Toth; J E Ray; J A Dodge; D W Johnson; P G Rutherford; R M Schultz; J F Worzalla; C J Vlahos
Journal:  J Med Chem       Date:  1996-03-01       Impact factor: 7.446

4.  Molecular pharmacology and antitumor activity of PX-866, a novel inhibitor of phosphoinositide-3-kinase signaling.

Authors:  Nathan T Ihle; Ryan Williams; Sherry Chow; Wade Chew; Margareta I Berggren; Gillian Paine-Murrieta; Daniel J Minion; Robert J Halter; Peter Wipf; Robert Abraham; Lynn Kirkpatrick; Garth Powis
Journal:  Mol Cancer Ther       Date:  2004-07       Impact factor: 6.261

5.  Wortmannin binds specifically to 1-phosphatidylinositol 3-kinase while inhibiting guanine nucleotide-binding protein-coupled receptor signaling in neutrophil leukocytes.

Authors:  M Thelen; M P Wymann; H Langen
Journal:  Proc Natl Acad Sci U S A       Date:  1994-05-24       Impact factor: 11.205

6.  Reducing the peptidyl features of caspase-3 inhibitors: a structural analysis.

Authors:  Joseph W Becker; Jennifer Rotonda; Stephen M Soisson; Renee Aspiotis; Christopher Bayly; Sébastien Francoeur; Michel Gallant; Marga Garcia-Calvo; Andre Giroux; Erich Grimm; Yongxin Han; Dan McKay; Donald W Nicholson; Erin Peterson; Johanne Renaud; Sophie Roy; Nancy Thornberry; Robert Zamboni
Journal:  J Med Chem       Date:  2004-05-06       Impact factor: 7.446

7.  Wortmannin, a potent and selective inhibitor of phosphatidylinositol-3-kinase.

Authors:  G Powis; R Bonjouklian; M M Berggren; A Gallegos; R Abraham; C Ashendel; L Zalkow; W F Matter; J Dodge; G Grindey
Journal:  Cancer Res       Date:  1994-05-01       Impact factor: 12.701

8.  Synthesis and biological evaluation of synthetic viridins derived from C(20)-heteroalkylation of the steroidal PI-3-kinase inhibitor wortmannin.

Authors:  Peter Wipf; Daniel J Minion; Robert J Halter; Margareta I Berggren; Caroline B Ho; Gary G Chiang; Lynn Kirkpatrick; Robert Abraham; Garth Powis
Journal:  Org Biomol Chem       Date:  2004-06-14       Impact factor: 3.876

9.  Radiolabeling of catalytic subunits of PI 3-kinases with 17 beta-hydroxy-16 alpha(-)[125I]iodowortmannin: identification of the G beta gamma-sensitive isoform as a complex composed of 46-kDa and 100-kDa subunits.

Authors:  H Kurosu; O Hazeki; I Kukimoto; S Honzawa; M Shibasaki; M Nakada; M Ui; T Katada
Journal:  Biochem Biophys Res Commun       Date:  1995-11-13       Impact factor: 3.575

10.  Structural determinants of phosphoinositide 3-kinase inhibition by wortmannin, LY294002, quercetin, myricetin, and staurosporine.

Authors:  E H Walker; M E Pacold; O Perisic; L Stephens; P T Hawkins; M P Wymann; R L Williams
Journal:  Mol Cell       Date:  2000-10       Impact factor: 17.970
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