The importance of intramolecular hydrogen bonds on the translocation of the small drug piracetam through a lipid bilayer.
Journal
RSC advances
ISSN: 2046-2069
Titre abrégé: RSC Adv
Pays: England
ID NLM: 101581657
Informations de publication
Date de publication:
24 Dec 2020
24 Dec 2020
Historique:
received:
25
11
2020
accepted:
02
12
2020
entrez:
15
4
2022
pubmed:
4
1
2021
medline:
4
1
2021
Statut:
epublish
Résumé
The number of hydrogen bond donors and acceptors is a fundamental molecular descriptor to predict the oral bioavailability of small drug candidates. In fact, the most widely used oral bioavailability rules (such as the Lipinsky's rule-of-five and the Veber rules) make use of this molecular descriptor. It is generally assumed that hydrogen bond donors and acceptors impact on passive diffusion across cell membranes, a fundamental event during drug absorption and distribution. Although the relationship between the number of these motifs and the probability of having good oral bioavailability has been studied and described for more than 20 years, little attention has been given to their spatial distribution in the molecule. In this paper, we used molecular dynamics to describe the effect of intramolecular hydrogen bonding on the passive diffusion of a small drug (piracetam) through a lipid membrane. The results indicated that the formation of an intramolecular hydrogen bond decreases the barrier for translocation by
Identifiants
pubmed: 35423709
doi: 10.1039/d0ra09995c
pii: d0ra09995c
pmc: PMC8693363
doi:
Types de publication
Journal Article
Langues
eng
Pagination
899-908Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts of interest to declare.
Références
J Mol Graph. 1996 Feb;14(1):33-8, 27-8
pubmed: 8744570
J Membr Biol. 1974;17(2):121-54
pubmed: 4407798
Phys Rev A Gen Phys. 1985 Mar;31(3):1695-1697
pubmed: 9895674
J Am Chem Soc. 2017 Jan 11;139(1):442-452
pubmed: 27951634
Adv Drug Deliv Rev. 2001 Mar 1;46(1-3):3-26
pubmed: 11259830
Protein Sci. 2014 May;23(5):652-61
pubmed: 24591301
Nat Rev Drug Discov. 2014 Jun;13(6):419-31
pubmed: 24833294
Biophys J. 2008 May 1;94(9):3393-404
pubmed: 18212019
Biochim Biophys Acta. 2016 Oct;1858(10):2483-2497
pubmed: 26766518
J Comput Chem. 2005 Dec;26(16):1701-18
pubmed: 16211538
Proc Natl Acad Sci U S A. 2017 Jun 13;114(24):E4724-E4733
pubmed: 28559343
J Comput Chem. 2004 Jul 15;25(9):1157-74
pubmed: 15116359
J Chem Theory Comput. 2015 Sep 8;11(9):4486-94
pubmed: 26575938
J Chem Theory Comput. 2014 Sep 9;10(9):4143-51
pubmed: 26588554
J Chem Theory Comput. 2015 Jun 9;11(6):2783-91
pubmed: 26575571
Chem Sci. 2019 Jun 11;10(30):7212-7221
pubmed: 31588289
J Med Chem. 2002 Jun 6;45(12):2615-23
pubmed: 12036371
J Org Chem. 2010 Mar 19;75(6):1831-40
pubmed: 20039621
Med Res Rev. 2019 Sep;39(5):1707-1729
pubmed: 30659634
J Chem Inf Model. 2016 Apr 25;56(4):721-33
pubmed: 27043429
Nat Rev Drug Discov. 2004 Aug;3(8):711-5
pubmed: 15286737
Drug Discov Today. 2012 Oct;17(19-20):1088-102
pubmed: 22627006
J Phys Chem B. 2009 Sep 3;113(35):12019-29
pubmed: 19663489
Adv Drug Deliv Rev. 2016 Jun 1;101:42-61
pubmed: 27067608
J Chem Theory Comput. 2020 Apr 14;16(4):2846-2856
pubmed: 32105473
J Med Chem. 2012 Apr 12;55(7):3163-9
pubmed: 22394492
PLoS Comput Biol. 2010 Jun 10;6(6):e1000810
pubmed: 20548957
BMC Res Notes. 2012 Jul 23;5:367
pubmed: 22824207
J Comput Chem. 2008 Aug;29(11):1859-65
pubmed: 18351591
J Chem Theory Comput. 2012 Aug 14;8(8):2938-48
pubmed: 26592132
J Med Chem. 1995 Jan 6;38(1):170-9
pubmed: 7837228
Phys Chem Chem Phys. 2013 Apr 7;15(13):4677-86
pubmed: 23439978
Adv Protein Chem. 2005;72:1-38
pubmed: 16581371
Nat Commun. 2014;5:3215
pubmed: 24477114
J Phys Chem B. 2012 Mar 15;116(10):3164-79
pubmed: 22352995
J Chem Theory Comput. 2015 May 12;11(5):2234-44
pubmed: 26574422
J Am Chem Soc. 2006 Jan 11;128(1):125-30
pubmed: 16390139
J Med Chem. 2010 Mar 25;53(6):2601-11
pubmed: 20175530
Biochim Biophys Acta. 2016 Oct;1858(10):2254-2265
pubmed: 27085977
J Chem Inf Model. 2016 Aug 22;56(8):1547-62
pubmed: 27387150
J Chem Theory Comput. 2011 Dec 13;7(12):4175-88
pubmed: 26598360
Biophys J. 2005 Apr;88(4):2472-93
pubmed: 15665128
ACS Cent Sci. 2019 Feb 27;5(2):290-298
pubmed: 30834317
J Chem Theory Comput. 2018 Jul 10;14(7):3840-3848
pubmed: 29864284
J Am Chem Soc. 2006 Nov 1;128(43):14073-80
pubmed: 17061890
Angew Chem Int Ed Engl. 2019 Mar 18;58(12):3759-3763
pubmed: 30681249
J Mol Graph Model. 2006 Oct;25(2):247-60
pubmed: 16458552
J Chem Phys. 2007 Jan 7;126(1):014101
pubmed: 17212484
Nat Rev Drug Discov. 2007 Nov;6(11):881-90
pubmed: 17971784
J Comput Chem. 2014 Oct 15;35(27):1997-2004
pubmed: 25130509
CNS Drug Rev. 2005 Summer;11(2):169-82
pubmed: 16007238
Biophys J. 2014 Aug 5;107(3):630-641
pubmed: 25099802
J Chem Theory Comput. 2013 Jan 8;9(1):687-97
pubmed: 26589065