Literature DB >> 30108724

The use of matched molecular series networks for cross target structure activity relationship translation and potency prediction.

Christopher E Keefer1, George Chang1.   

Abstract

Matched molecular series (MMS) analysis is an extension of matched molecular pair (MMP) analysis where all of the MMPs belong to the same chemical series. An MMS within a biological assay is able to capture specific structure activity relationships resulting from chemical substitution at a single location in the molecule. Under this convention, an MMS has the ability to capture one specific interaction vector between the compounds in a series and their therapeutic target. MMS analysis has the potential to translate the SAR from one series to another even across different protein targets or assays. A significant limitation of this approach is the lack of chemical series with a sufficient number of overlapping fragments to establish a statistically strong SAR in most databases. This results in either an inability to perform MMS analysis altogether or a potentially high proportion of spurious matches from chance correlations when the MMS compound count is low. This paper presents the novel concept of an MMS Network, which captures the SAR relationships between a set of related MMSs and significantly enhances the performance of MMS analysis by reducing the number of spurious matches leading to the identification of unexpected and potentially transferable SAR across assays. The results of a full retrospective leave-one-out analysis and randomization simulation are provided, and examples of pharmaceutically relevant programs will be presented to demonstrate the potential of this method.

Entities:  

Year:  2017        PMID: 30108724      PMCID: PMC6072506          DOI: 10.1039/c7md00465f

Source DB:  PubMed          Journal:  Medchemcomm        ISSN: 2040-2503            Impact factor:   3.597


  17 in total

1.  Lead optimization using matched molecular pairs: inclusion of contextual information for enhanced prediction of HERG inhibition, solubility, and lipophilicity.

Authors:  George Papadatos; Muhammad Alkarouri; Valerie J Gillet; Peter Willett; Visakan Kadirkamanathan; Christopher N Luscombe; Gianpaolo Bravi; Nicola J Richmond; Stephen D Pickett; Jameed Hussain; John M Pritchard; Anthony W J Cooper; Simon J F Macdonald
Journal:  J Chem Inf Model       Date:  2010-10-25       Impact factor: 4.956

2.  Matched molecular pairs as a guide in the optimization of pharmaceutical properties; a study of aqueous solubility, plasma protein binding and oral exposure.

Authors:  Andrew G Leach; Huw D Jones; David A Cosgrove; Peter W Kenny; Linette Ruston; Philip MacFaul; J Matthew Wood; Nicola Colclough; Brian Law
Journal:  J Med Chem       Date:  2006-11-16       Impact factor: 7.446

3.  Statistical analysis of the effects of common chemical substituents on ligand potency.

Authors:  Philip J Hajduk; Daryl R Sauer
Journal:  J Med Chem       Date:  2008-01-04       Impact factor: 7.446

4.  Local structural changes, global data views: graphical substructure-activity relationship trailing.

Authors:  Mathias Wawer; Jürgen Bajorath
Journal:  J Med Chem       Date:  2011-03-28       Impact factor: 7.446

5.  Extraction of tacit knowledge from large ADME data sets via pairwise analysis.

Authors:  Christopher E Keefer; George Chang; Gregory W Kauffman
Journal:  Bioorg Med Chem       Date:  2011-05-06       Impact factor: 3.641

6.  Systematic assessment of compound series with SAR transfer potential.

Authors:  Bijun Zhang; Anne Mai Wassermann; Martin Vogt; Jürgen Bajorath
Journal:  J Chem Inf Model       Date:  2012-12-06       Impact factor: 4.956

7.  Application of Structure-Based Design and Parallel Chemistry to Identify a Potent, Selective, and Brain Penetrant Phosphodiesterase 2A Inhibitor.

Authors:  Christopher J Helal; Eric P Arnold; Tracey L Boyden; Cheng Chang; Thomas A Chappie; Kimberly F Fennell; Michael D Forman; Mihaly Hajos; John F Harms; William E Hoffman; John M Humphrey; Zhijun Kang; Robin J Kleiman; Bethany L Kormos; Che-Wah Lee; Jiemin Lu; Noha Maklad; Laura McDowell; Scot Mente; Rebecca E O'Connor; Jayvardhan Pandit; Mary Piotrowski; Anne W Schmidt; Christopher J Schmidt; Hirokazu Ueno; Patrick R Verhoest; Edward X Yang
Journal:  J Med Chem       Date:  2017-06-16       Impact factor: 7.446

8.  Using matched molecular series as a predictive tool to optimize biological activity.

Authors:  Noel M O'Boyle; Jonas Boström; Roger A Sayle; Adrian Gill
Journal:  J Med Chem       Date:  2014-03-14       Impact factor: 7.446

Review 9.  Matched Molecular Pair Analysis in Short: Algorithms, Applications and Limitations.

Authors:  Christian Tyrchan; Emma Evertsson
Journal:  Comput Struct Biotechnol J       Date:  2016-12-13       Impact factor: 7.271

10.  Strong nonadditivity as a key structure-activity relationship feature: distinguishing structural changes from assay artifacts.

Authors:  Christian Kramer; Julian E Fuchs; Klaus R Liedl
Journal:  J Chem Inf Model       Date:  2015-03-11       Impact factor: 4.956

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  2 in total

1.  CAVIAR: a method for automatic cavity detection, description and decomposition into subcavities.

Authors:  Jean-Rémy Marchand; Bernard Pirard; Peter Ertl; Finton Sirockin
Journal:  J Comput Aided Mol Des       Date:  2021-05-29       Impact factor: 3.686

2.  BRADSHAW: a system for automated molecular design.

Authors:  Darren V S Green; Stephen Pickett; Chris Luscombe; Stefan Senger; David Marcus; Jamel Meslamani; David Brett; Adam Powell; Jonathan Masson
Journal:  J Comput Aided Mol Des       Date:  2019-10-21       Impact factor: 3.686

  2 in total

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