Drug Discovery Based on Fluorine-Containing Glycomimetics.
drug discovery
fluorination
glycomimetics
physical properties
synthesis
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
15 Sep 2023
15 Sep 2023
Historique:
received:
31
08
2023
revised:
12
09
2023
accepted:
13
09
2023
medline:
4
10
2023
pubmed:
28
9
2023
entrez:
28
9
2023
Statut:
epublish
Résumé
Glycomimetics, which are synthetic molecules designed to mimic the structures and functions of natural carbohydrates, have been developed to overcome the limitations associated with natural carbohydrates. The fluorination of carbohydrates has emerged as a promising solution to dramatically enhance the metabolic stability, bioavailability, and protein-binding affinity of natural carbohydrates. In this review, the fluorination methods used to prepare the fluorinated carbohydrates, the effects of fluorination on the physical, chemical, and biological characteristics of natural sugars, and the biological activities of fluorinated sugars are presented.
Identifiants
pubmed: 37764416
pii: molecules28186641
doi: 10.3390/molecules28186641
pmc: PMC10536126
pii:
doi:
Substances chimiques
Fluorine
284SYP0193
Carbohydrates
0
Sugars
0
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : the National Natural Science Foundation of China
ID : Nos. 21977003, 22007003
Références
Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9597-602
pubmed: 25044775
Biochemistry. 1997 Jan 28;36(4):823-31
pubmed: 9020780
Nat Chem Biol. 2012 Jul;8(7):661-8
pubmed: 22683610
Molecules. 2023 Feb 17;28(4):
pubmed: 36838925
Chem Rev. 1996 Aug 1;96(5):1737-1756
pubmed: 11848809
ChemMedChem. 2017 Jun 7;12(11):819-829
pubmed: 28498640
Proc Natl Acad Sci U S A. 2008 Oct 14;105(41):15684-9
pubmed: 18838688
Chemistry. 2009 Jun 2;15(23):5666-8
pubmed: 19388026
J Am Chem Soc. 2007 Sep 12;129(36):11042-4
pubmed: 17711286
Nat Rev Drug Discov. 2005 Jun;4(6):477-88
pubmed: 15931257
Carbohydr Res. 2000 Nov 17;329(3):539-47
pubmed: 11128583
Biomimetics (Basel). 2019 Jul 28;4(3):
pubmed: 31357673
Proc Natl Acad Sci U S A. 2013 Feb 12;110(7):2466-71
pubmed: 23359711
J Biomed Sci. 2020 Jan 3;27(1):9
pubmed: 31900143
Science. 2013 Apr 5;340(6128):71-5
pubmed: 23429702
Chemistry. 2014 Jan 3;20(1):106-12
pubmed: 24311368
Carbohydr Res. 2011 Jul 1;346(9):1129-39
pubmed: 21531398
Chemistry. 2017 May 2;23(25):6142-6149
pubmed: 27788283
Beilstein J Org Chem. 2010 Apr 20;6:38
pubmed: 20502650
Angew Chem Int Ed Engl. 2019 Sep 23;58(39):13758-13762
pubmed: 31348606
J Am Chem Soc. 2003 Jun 25;125(25):7532-3
pubmed: 12812490
Org Biomol Chem. 2011 Aug 7;9(15):5541-6
pubmed: 21695336
Chem Rev. 2022 Oct 26;122(20):15503-15602
pubmed: 35613331
Biochemistry. 2000 Jan 11;39(1):117-26
pubmed: 10625486
FEBS J. 2022 Jul;289(14):4251-4303
pubmed: 33934527
ACS Omega. 2019 Aug 19;4(9):13618-13630
pubmed: 31497679
Org Lett. 2007 Apr 12;9(8):1441-4
pubmed: 17358072
Med Res Rev. 2018 May;38(3):1003-1026
pubmed: 29512174
Angew Chem Int Ed Engl. 2010 Nov 2;49(45):8498-503
pubmed: 20878823
Structure. 2004 May;12(5):775-84
pubmed: 15130470
Chem Commun (Camb). 2015 Feb 18;51(14):2933-5
pubmed: 25587931
J Am Chem Soc. 2002 Mar 27;124(12):3175-85
pubmed: 11902907
Biomolecules. 2015 Nov 13;5(4):3177-92
pubmed: 26580665
Bioconjug Chem. 2022 May 18;33(5):807-820
pubmed: 35470665
J Org Chem. 2018 Aug 3;83(15):8150-8160
pubmed: 29916255
Angew Chem Int Ed Engl. 2008;47(14):2700-3
pubmed: 18300214
Biochemistry. 1986 Oct 7;25(20):6021-7
pubmed: 3790503
Beilstein J Org Chem. 2015 Jan 23;11:155-161
pubmed: 25670999
FASEB J. 2015 Jul;29(7):2993-3002
pubmed: 25868729
Org Lett. 2015 Nov 20;17(22):5698-701
pubmed: 26562610
J Org Chem. 2016 Jun 3;81(11):4434-53
pubmed: 27014960
Carbohydr Res. 2000 Jul 10;327(1-2):5-14
pubmed: 10968673
ACS Chem Biol. 2011 Mar 18;6(3):252-9
pubmed: 21121644
Angew Chem Int Ed Engl. 2016 Jan 11;55(2):674-8
pubmed: 26592706
ChemMedChem. 2009 Jan;4(1):49-51
pubmed: 19065645
Carbohydr Res. 2006 Mar 20;341(4):457-66
pubmed: 16413000
J Org Chem. 2021 Nov 19;86(22):16187-16194
pubmed: 34435785
J Org Chem. 2020 Dec 18;85(24):16072-16081
pubmed: 33258593
J Am Chem Soc. 2014 Dec 3;136(48):16844-53
pubmed: 25371992
Chem Commun (Camb). 2011 Sep 21;47(35):9903-5
pubmed: 21818465
ACS Nano. 2015 Jan 27;9(1):733-45
pubmed: 25575241
Chem Soc Rev. 2013 May 21;42(10):4459-75
pubmed: 23588106
Nat Rev Drug Discov. 2011 Mar;10(3):197-208
pubmed: 21358739
Biochem J. 1994 Jul 15;301 ( Pt 2):343-8
pubmed: 8042975
Org Biomol Chem. 2004 Mar 7;2(5):725-31
pubmed: 14985813
J Org Chem. 2009 Aug 21;74(16):5779-89
pubmed: 19958035
ChemMedChem. 2016 May 19;11(10):1090-6
pubmed: 27075633
Bioorg Med Chem. 2001 Dec;9(12):3077-92
pubmed: 11711283
Mol Cancer Ther. 2013 Oct;12(10):1935-46
pubmed: 23974695
Org Biomol Chem. 2019 May 29;17(21):5173-5189
pubmed: 31017598
Org Lett. 2020 Dec 4;22(23):9325-9330
pubmed: 33226829
Chemistry. 2009;15(12):2861-73
pubmed: 19185038
Chem Sci. 2020 Jan 8;11(7):1761-1774
pubmed: 34123271
Org Lett. 2018 Nov 2;20(21):6769-6773
pubmed: 30350649
Org Biomol Chem. 2017 Mar 1;15(9):2120-2121
pubmed: 28195591
Chemistry. 2021 May 20;27(29):7813-7825
pubmed: 33462910
J Org Chem. 2019 Dec 6;84(23):15087-15097
pubmed: 31580074
Mol Immunol. 1985 Jun;22(6):651-3
pubmed: 3839564
J Med Chem. 2019 Jan 24;62(2):1014-1021
pubmed: 30543426
J Antibiot (Tokyo). 1967 Mar;20(2):66-71
pubmed: 6072426
Chem Biol. 2010 Apr 23;17(4):357-70
pubmed: 20416507
Oncotarget. 2017 Jul 18;8(29):47330-47343
pubmed: 28537884
Chembiochem. 2004 May 3;5(5):622-7
pubmed: 15122633
Bioorg Med Chem. 2016 Feb 15;24(4):915-20
pubmed: 26787275
Chem Commun (Camb). 2018 May 8;54(38):4761-4769
pubmed: 29662983
Biochim Biophys Acta. 2016 Jan;1864(1):143-53
pubmed: 26192491
Glycobiology. 2006 Feb;16(2):29R-37R
pubmed: 16037492
Nat Commun. 2018 Nov 9;9(1):4721
pubmed: 30413697
Biochemistry. 2014 Apr 22;53(15):2494-504
pubmed: 24689960
Org Biomol Chem. 2020 May 13;18(18):3423-3451
pubmed: 32319497
Org Lett. 2013 Jul 5;15(13):3428-31
pubmed: 23790056
J Biol Chem. 1995 Nov 10;270(45):26778-81
pubmed: 7592915
Carbohydr Res. 2000 Jul 10;327(1-2):27-46
pubmed: 10968675
Org Lett. 2007 Jun 21;9(13):2477-80
pubmed: 17530855
Org Biomol Chem. 2015 Jul 21;13(27):7542-50
pubmed: 26072729
Carbohydr Res. 1990 May 1;198(2):205-21
pubmed: 2379186
J Med Chem. 2013 Mar 14;56(5):1789-95
pubmed: 23356819
Org Biomol Chem. 2015 Jun 14;13(22):6399-406
pubmed: 25982227
Angew Chem Int Ed Engl. 2020 Mar 2;59(10):4138-4144
pubmed: 31850616
J Org Chem. 2019 May 3;84(9):5899-5906
pubmed: 30869517
Angew Chem Int Ed Engl. 2004 Dec 27;44(2):192-212
pubmed: 15578736
Chemistry. 2010 Jun 25;16(24):7319-30
pubmed: 20461825
Chem Commun (Camb). 2010 Aug 14;46(30):5434-6
pubmed: 20532277
J Am Chem Soc. 2021 Jul 28;143(29):11171-11179
pubmed: 34260212
Nat Struct Mol Biol. 2004 Sep;11(9):857-62
pubmed: 15311269
J Am Chem Soc. 2007 Dec 19;129(50):15420-1
pubmed: 18034482
Chemistry. 2018 Oct 22;24(59):15761-15765
pubmed: 30276889
Nat Rev Drug Discov. 2009 Aug;8(8):661-77
pubmed: 19629075
FEBS J. 2006 Oct;273(20):4716-27
pubmed: 16995857
Trends Cell Biol. 2001 Feb;11(2):75-82
pubmed: 11166215
Bioorg Med Chem. 2000 Aug;8(8):1937-46
pubmed: 11003139
Chem Commun (Camb). 2012 Feb 1;48(10):1487-9
pubmed: 21986937
Cancer Res. 2018 Jul 1;78(13):3574-3588
pubmed: 29703719
J Med Chem. 2015 Nov 25;58(22):9041-60
pubmed: 26523333
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3386-90
pubmed: 22345046
Tetrahedron. 1968 Mar;24(5):2125-44
pubmed: 5636917
Chemistry. 2018 Feb 26;24(12):2832-2836
pubmed: 29211300
Carbohydr Res. 2000 Jul 10;327(1-2):47-86
pubmed: 10968676
Chemistry. 2020 Oct 21;26(59):13499-13506
pubmed: 32652740
Curr Top Med Chem. 2014;14(7):865-74
pubmed: 24484426
Carbohydr Res. 2010 May 27;345(8):984-93
pubmed: 20347069
Blood. 2010 Feb 11;115(6):1303-12
pubmed: 19996411
Science. 2007 Sep 28;317(5846):1881-6
pubmed: 17901324
Chem Soc Rev. 2020 Jun 22;49(12):3863-3888
pubmed: 32520059
Trends Microbiol. 2018 Feb;26(2):92-101
pubmed: 29079498
J Enzyme Inhib Med Chem. 2007 Oct;22(5):527-40
pubmed: 18035820
Pharmaceuticals (Basel). 2019 Apr 11;12(2):
pubmed: 30978966
Carbohydr Res. 1992 Jul 20;232(1):89-105
pubmed: 1423353
J Org Chem. 2016 Jun 3;81(11):4736-43
pubmed: 27152753
Carbohydr Res. 2018 May 23;465:4-9
pubmed: 29874559
Nat Rev Cancer. 2005 Jul;5(7):526-42
pubmed: 16069816
Chem Soc Rev. 2013 May 21;42(10):4270-83
pubmed: 23212149
Chemistry. 2013 Apr 22;19(17):5364-74
pubmed: 23447543
Org Biomol Chem. 2021 Jun 30;19(25):5439-5475
pubmed: 33881114
Glycobiology. 2008 Aug;18(8):570-86
pubmed: 18499865
Chemistry. 2021 Feb 1;27(7):2240-2253
pubmed: 32901973
Discov Med. 2009 Dec;8(43):247-52
pubmed: 20040279
J Biol Chem. 2011 Jun 17;286(24):21717-31
pubmed: 21493714
Org Biomol Chem. 2020 Nov 4;18(42):8724-8734
pubmed: 33089846
J Fluor Chem. 2008 Sep;129(9):743-766
pubmed: 19727318