Literature DB >> 26641132

Novel Microtubule-Targeting 7-Deazahypoxanthines Derived from Marine Alkaloid Rigidins with Potent in Vitro and in Vivo Anticancer Activities.

Derek C Medellin1, Qiong Zhou2, Robert Scott1, R Matthew Hill1, Sarah K Frail3, Ramesh Dasari1, Steven J Ontiveros4, Stephen C Pelly5, Willem A L van Otterlo5, Tania Betancourt1,6, Charles B Shuster4, Ernest Hamel7, Ruoli Bai7, Daniel V LaBarbera2, Snezna Rogelj3, Liliya V Frolova3, Alexander Kornienko1.   

Abstract

Docking studies of tubulin-targeting C2-substituted 7-deazahypoxanthine analogues of marine alkaloid rigidins led to the design and synthesis of compounds containing linear C2-substituents. The C2-alkynyl analogue was found to have double- to single-digit nanomolar antiproliferative IC50 values and showed statistically significant tumor size reduction in a colon cancer mouse model at nontoxic concentrations. These results provide impetus and further guidance for the development of these rigidin analogues as anticancer agents.

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Year:  2015        PMID： 26641132      PMCID： PMC4950951          DOI： 10.1021/acs.jmedchem.5b01426

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  9 in total

Review 1.  Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin.

Authors:  Ernest Hamel
Journal:  Cell Biochem Biophys       Date:  2003       Impact factor: 2.194

2.  Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin.

Authors:  C M Lin; H H Ho; G R Pettit; E Hamel
Journal:  Biochemistry       Date:  1989-08-22       Impact factor: 3.162

Review 3.  Marine natural products as anticancer drugs.

Authors:  T Luke Simmons; Eric Andrianasolo; Kerry McPhail; Patricia Flatt; William H Gerwick
Journal:  Mol Cancer Ther       Date:  2005-02       Impact factor: 6.261

4.  Structural plasticity of tubulin assembly probed by vinca-domain ligands.

Authors:  Fanomezana M Ranaivoson; Benoît Gigant; Simon Berritt; Madeleine Joullié; Marcel Knossow
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2012-07-07

5.  One-pot multicomponent synthesis of diversely substituted 2-aminopyrroles. A short general synthesis of rigidins A, B, C, and D.

Authors:  Liliya V Frolova; Nikolai M Evdokimov; Kathryn Hayden; Indranil Malik; Snezna Rogelj; Alexander Kornienko; Igor V Magedov
Journal:  Org Lett       Date:  2011-01-26       Impact factor: 6.005

6.  Exploring natural product chemistry and biology with multicomponent reactions. 5. Discovery of a novel tubulin-targeting scaffold derived from the rigidin family of marine alkaloids.

Authors:  Liliya V Frolova; Igor V Magedov; Anntherese E Romero; Menuka Karki; Isaiah Otero; Kathryn Hayden; Nikolai M Evdokimov; Laetitia Moreno Y Banuls; Shiva K Rastogi; W Ross Smith; Shi-Long Lu; Robert Kiss; Charles B Shuster; Ernest Hamel; Tania Betancourt; Snezna Rogelj; Alexander Kornienko
Journal:  J Med Chem       Date:  2013-08-23       Impact factor: 7.446

7.  Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells.

Authors:  P Verdier-Pinard; J Y Lai; H D Yoo; J Yu; B Marquez; D G Nagle; M Nambu; J D White; J R Falck; W H Gerwick; B W Day; E Hamel
Journal:  Mol Pharmacol       Date:  1998-01       Impact factor: 4.436

8.  Synthetic and biological studies of tubulin targeting c2-substituted 7-deazahypoxanthines derived from marine alkaloid rigidins.

Authors:  Robert Scott; Menuka Karki; Mary R Reisenauer; Roberta Rodrigues; Ramesh Dasari; W Ross Smith; Stephen C Pelly; Willem A L van Otterlo; Charles B Shuster; Snezna Rogelj; Igor V Magedov; Liliya V Frolova; Alexander Kornienko
Journal:  ChemMedChem       Date:  2014-03-18       Impact factor: 3.466

Review 9.  Trabectedin in soft tissue sarcomas.

Authors:  Bradley J Petek; Elizabeth T Loggers; Seth M Pollack; Robin L Jones
Journal:  Mar Drugs       Date:  2015-02-12       Impact factor: 5.118
  9 in total
  3 in total

1.  Microtubule-Targeting 7-Deazahypoxanthines Derived from Marine Alkaloid Rigidins: Exploration of the N3 and N9 Positions and Interaction with Multidrug-Resistance Proteins.

Authors:  Ramesh Dasari; Andrzej Błauż; Derek C Medellin; Roaa M Kassim; Carlos Viera; Maximo Santarosa; Alet E van der Westhuyzen; Willem A L van Otterlo; Taryn Olivas; Tugba Yildiz; Tania Betancourt; Charles B Shuster; Snezna Rogelj; Błażej Rychlik; Todd Hudnall; Liliya V Frolova; Alexander Kornienko
Journal:  ChemMedChem       Date:  2019-01-25       Impact factor: 3.466

2.  Polygodial and Ophiobolin A Analogues for Covalent Crosslinking of Anticancer Targets.

Authors:  Vladimir Maslivetc; Breana Laguera; Sunena Chandra; Ramesh Dasari; Wesley J Olivier; Jason A Smith; Alex C Bissember; Marco Masi; Antonio Evidente; Veronique Mathieu; Alexander Kornienko
Journal:  Int J Mol Sci       Date:  2021-10-19       Impact factor: 5.923

Review 3.  Marine Alkaloids: Compounds with In Vivo Activity and Chemical Synthesis.

Authors:  Paulo E S Munekata; Mirian Pateiro; Carlos A Conte-Junior; Rubén Domínguez; Asad Nawaz; Noman Walayat; Elena Movilla Fierro; José M Lorenzo
Journal:  Mar Drugs       Date:  2021-06-28       Impact factor: 5.118
  3 in total

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