Molecular descriptors for polarity: The need for going beyond polar surface area

Future Medicinal Chemistry

Volumn 8, Issue 17, 2016, Pages 2013-2016

  Caron, Giulia ^a   Ermondi, Giuseppe ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

hydrogen bonding; polar surface area; polarity; topological polar surface area

Indexed keywords

HYDROGEN; NEW DRUG;

CHEMICAL STRUCTURE; DIPOLE; DRUG CONFORMATION; DRUG DEVELOPMENT; HYDROGEN BOND; NOTE; PRIORITY JOURNAL; SURFACE AREA;

EID: 84993971886     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc-2016-0165     Document Type: Note

References (28)

1. Wang J, Skolnik S. Permeability diagnosis model in drug discovery: a diagnostic tool to identify the most influencing properties for gastrointestinal permeation. Curr. Top. Med. Chem. 13, 1308-1316 (2013).
2. Goodwin JT, Clark DE. In silico predictions of blood-brain barrier penetration: considerations to "keep in mind". J. Pharmacol. Exp. Ther. 315(2), 477-483 (2005).
3. Palm K, Stenberg P, Luthman K, Artursson P. Polar molecular surface properties predict the intestinal absorption of drugs in humans. Pharm. Res. 14(5), 568-571 (1997).
4. Atkins P, De Paula J. Physical Chemistry (8th Edition). Oxford University Press, Oxford, UK, 621-623 (2006).
5. Guimarães CRW, Mathiowetz AM, Shalaeva M et al. Use of 3D properties to characterize beyond rule-of-5 property space for passive permeation. J. Chem. Inf. Model. 52, 882-890 (2012).
6. Clark D.E. What has polar surface area ever done for drug discovery?. Fut. Med. Chem. 3(4), 469-484 (2011).
7. Ertl P, Rohde B, Selzer P. Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties. J. Med. Chem. 43, 3714-3717 (2000).
8. Ertl P. Polar surface area. In: Molecular Drug Properties. Measurement and Prediction. Mannhold R (Ed.). Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 111-126 (2008).
9. Rey S, Caron G, Ermondi G et al. Development of molecular hydrogen-bonding potentials (MHBPs) and their application to structure-permeation relations. J. Mol. Graph. Model. 19(6), 521-535 (2001).
10. Potter T, Ermondi G, Newbury G et al. Relating Caco-2 permeability to molecular properties using block relevance analysis. Med. Chem. Commun. 6, 626-629 (2014).
11. Laurence C, Brameld KA, Graton J et al. The pKBHX database: toward a better understanding of hydrogenbond basicity for medicinal chemists. J. Med. Chem. 52, 4073-4086 (2009).
12. Goetz GH, Farrell W, Shalaeva M et al. High throughput method for the indirect detection of intramolecular hydrogen bonding. J. Med. Chem. 57(7), 2920-2929 (2014).
13. Goetz GH, Philippe L, Shapiro MJ. EPSA: a novel supercritical fluid chromatography technique enabling the design of permeable cyclic peptides. ACS Med. Chem. Lett. 5(10), 1167-1172 (2014).
14. Testa B, Carrupt P-A, Gaillard P et al. Intramolecular interactions encoded in lipophilicity: their nature and significance. In: Lipophilicity in Drug Action and Toxicology. Pliska V, Testa B, van de Waterbeemd H (Eds.). Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 49-71 (1996).
15. Ermondi G, Visconti A, Esposito R et al. The Block Relevance (BR) analysis supports the dominating effect of solutes hydrogen bond acidity on ΔlogP(oct-tol). Eur. J. Pharm. Sci. 53, 50-54 (2014).
16. Bergström CAS, Strafford M, Lazorova L et al. Absorption classification of oral drugs based on molecular surface properties. J. Med. Chem. 46, 558-570 (2003).
17. Saunders RA, Platts JA. Scaled polar surface area descriptors: development and application to three sets of partition coefficients. New J. Chem. 28, 166-172 (2004).
18. Abraham MH, Acree WE Jr, Leo AJ et al. Water-solvent partition coefficients and Delta Log P values as predictors for blood-brain distribution; application of the Akaike information criterion. J. Pharm. Sci. 99(5), 2492-2501 (2010).
19. Bytheway I, Darley MG, Popelier PLA. The calculation of polar surface area from first principles: an application of quantum chemical topology to drug design. ChemMedChem 3(3), 445-453 (2008).
20. Murray JS, Politzer P. Correlations between the solvent hydrogen-bond-donating parameter alpha and the calculated molecular surface electrostatic potential. J. Org. Chem. 56(16), 6715-6717 (1991).
21. Cruciani G, Crivori P, Carrupt PA et al. Molecular fields in quantitative structure-permeation relationships: the VolSurf approach. J. Mol. Struct. (Theochem.) 503, 17-30 (2000).
22. Goodford PJ. A computational procedure for determining energetically favorable binding sites on biologically important macromolecules. J. Med. Chem. 28(7), 849-857 (1985).
23. Ermondi G, Caron G. Molecular interaction fields based descriptors to interpret and compare chromatographic indexes. J. Chromatogr. A. 1252, 84-89 (2012).
24. Caron G, Vallaro M, Ermondi G. The Block Relevance (BR) analysis to aid medicinal chemists to determine and interpret lipophilicity. Med. Chem. Comm. 4(10), 1376-1381 (2013).
25. Caron G, Visentin S, Pontremoli C et al. Profile of the intermolecular forces governing the interaction of drugs with mucin. Int. J. Pharm. 488(1-2), 67-69 (2015).
26. Caron G, Vallaro M, Ermondi G et al. A fast chromatographic method for estimating lipophilicity and ionization in nonpolar membrane-like environment. Mol. Pharm. 13, 1100-1110 (2016).
27. Giordanetto F, Kihlberg J. Macrocyclic drugs and clinical candidates: what can medicinal chemists learn from their properties?. J. Med. Chem. 57(2), 278-295 (2014).
28. Whitty A, Zhong M, Viarengo L et al. Quantifying the chameleonic properties of macrocycles and other highmolecular-weight drugs. Drug Discov. Today. 21(5), 712-717 (2016).