Recent progress in the development of steroid sulphatase inhibitors - examples of the novel and most promising compounds from the last decade.


Journal

Journal of enzyme inhibition and medicinal chemistry
ISSN: 1475-6374
Titre abrégé: J Enzyme Inhib Med Chem
Pays: England
ID NLM: 101150203

Informations de publication

Date de publication:
Dec 2020
Historique:
entrez: 5 5 2020
pubmed: 5 5 2020
medline: 2 1 2021
Statut: ppublish

Résumé

The purpose of this review article is to provide an overview of recent achievements in the synthesis of novel steroid sulphatase (STS) inhibitors. STS is a crucial enzyme in the biosynthesis of active hormones (including oestrogens and androgens) and, therefore, represents an extremely attractive molecular target for the development of hormone-dependent cancer therapies. The inhibition of STS may effectively reduce the availability of active hormones for cancer cells, causing a positive therapeutic effect. Herein, we report examples of novel STS inhibitors based on steroidal and nonsteroidal cores that contain various functional groups (e.g. sulphamate and phosphorus moieties) and halogen atoms, which may potentially be used in therapies for hormone-dependent cancers. The presented work also includes examples of multitargeting agents with STS inhibitory activities. Furthermore, the fundamental discoveries in the development of the most promising drug candidates exhibiting STS inhibitory activities are highlighted.

Identifiants

pubmed: 32363947
doi: 10.1080/14756366.2020.1758692
pmc: PMC7241464
doi:

Substances chimiques

Enzyme Inhibitors 0
STS protein, human EC 3.1.6.2
Steryl-Sulfatase EC 3.1.6.2

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

1163-1184

Références

J Asian Nat Prod Res. 2015;17(11):1091-6
pubmed: 26269086
J Med Chem. 2011 Jul 14;54(13):4863-79
pubmed: 21604672
J Med Chem. 2006 Dec 28;49(26):7683-96
pubmed: 17181151
J Med Chem. 2007 Jul 26;50(15):3540-60
pubmed: 17580845
ChemMedChem. 2011 Aug 1;6(8):1423-38
pubmed: 21608133
Br J Cancer. 2004 Feb 23;90(4):932-7
pubmed: 14970876
J Med Chem. 2003 Jul 17;46(15):3193-6
pubmed: 12852749
J Med Chem. 2010 Mar 11;53(5):2155-70
pubmed: 20148564
J Steroid Biochem Mol Biol. 2000 Dec 31;75(4-5):253-8
pubmed: 11282279
ACS Med Chem Lett. 2010 Dec 29;2(3):243-7
pubmed: 24900302
Chem Biol Drug Des. 2017 Jul;90(1):156-161
pubmed: 28032462
J Med Chem. 2017 May 11;60(9):4086-4092
pubmed: 28406629
Breast Cancer Res Treat. 2017 Sep;165(2):343-353
pubmed: 28612226
Horm Behav. 2016 Jul;83:83-92
pubmed: 27222435
J Biol Chem. 2003 Jun 20;278(25):22989-97
pubmed: 12657638
Drug Dev Res. 2019 Sep;80(6):857-866
pubmed: 31301181
Breast Cancer Res Treat. 2017 Nov;166(2):527-539
pubmed: 28795252
J Steroid Biochem Mol Biol. 1995 Dec;55(3-4):395-403
pubmed: 8541236
Int J Gynecol Cancer. 2017 Feb;27(2):258-266
pubmed: 27870712
Recent Pat Endocr Metab Immune Drug Discov. 2015;9(1):15-23
pubmed: 25643356
Eur J Med Chem. 2016 Aug 25;119:169-82
pubmed: 27155470
ChemMedChem. 2011 Nov 4;6(11):2019-34
pubmed: 21990014
Eur J Biochem. 1996 Jun 1;238(2):341-5
pubmed: 8681943
J Med Chem. 1994 Jan 21;37(2):219-21
pubmed: 8295207
Bioorg Chem. 2020 Mar;96:103618
pubmed: 32059152
J Steroid Biochem Mol Biol. 2003 Feb;84(2-3):351-8
pubmed: 12711022
J Steroid Biochem Mol Biol. 1996 Aug;58(5-6):611-7
pubmed: 8918989
J Med Chem. 2008 Jul 24;51(14):4226-38
pubmed: 18590272
Clin Cancer Res. 2008 Jan 15;14(2):597-606
pubmed: 18223236
Clin Cancer Res. 2008 Oct 15;14(20):6469-77
pubmed: 18927286
Bioorg Med Chem. 2012 Apr 15;20(8):2506-19
pubmed: 22455789
J Steroid Biochem Mol Biol. 2005 Feb;94(1-3):219-27
pubmed: 15862969
J Med Chem. 2000 Nov 16;43(23):4465-78
pubmed: 11087571
Drug Dev Res. 2015 Dec;76(8):450-62
pubmed: 26415657
ACS Omega. 2018 Sep 30;3(9):10748-10772
pubmed: 30320251
J Steroid Biochem Mol Biol. 2011 May;125(1-2):39-45
pubmed: 21356310
Drug Dev Res. 2015 Mar;76(2):94-104
pubmed: 25845343
Reprod Fertil Dev. 2001;13(4):297-305
pubmed: 11800168
Bioorg Chem. 2020 Jan;95:103495
pubmed: 31855822
Endocr Relat Cancer. 2018 May;25(5):R283-R301
pubmed: 29530940
Eur J Med Chem. 2016 May 23;114:170-90
pubmed: 26974384
Bioorg Med Chem. 2020 Apr 1;28(7):115368
pubmed: 32122754
J Steroid Biochem Mol Biol. 2015 Sep;153:160-9
pubmed: 25843211
Br J Cancer. 2008 Dec 2;99(11):1842-8
pubmed: 18985042
Eur J Med Chem. 2015 Aug 28;101:358-66
pubmed: 26163883
Pharm Res. 2015 Apr;32(4):1493-504
pubmed: 25355461
Bioorg Med Chem. 2015 Sep 1;23(17):5681-92
pubmed: 26211459
Bioorg Med Chem. 2017 Dec 15;25(24):6417-6426
pubmed: 29102082
Life Sci. 1997;60(3):PL45-51
pubmed: 9000649
Endocr Rev. 2015 Oct;36(5):526-63
pubmed: 26213785
Bioorg Med Chem. 2012 Feb 15;20(4):1535-44
pubmed: 22264754
Front Pharmacol. 2016 Feb 18;7:30
pubmed: 26924986
Bioorg Med Chem. 2014 Apr 1;22(7):2244-52
pubmed: 24630694
J Endocrinol. 2012 Feb;212(2):99-110
pubmed: 21859802
Angew Chem Int Ed Engl. 2004 Nov 5;43(43):5736-63
pubmed: 15493058
Anticancer Agents Med Chem. 2008 Oct;8(7):732-8
pubmed: 18855575
J Mol Endocrinol. 2018 Aug;61(2):T233-T252
pubmed: 29618488
Clin Cancer Res. 2006 Mar 1;12(5):1585-92
pubmed: 16533785
Steroids. 2012 Jul;77(8-9):864-70
pubmed: 22542502
J Asian Nat Prod Res. 2020 Nov;22(11):1037-1044
pubmed: 31773975
ChemMedChem. 2010 Sep 3;5(9):1577-93
pubmed: 20632362
J Steroid Biochem Mol Biol. 1996 Sep;59(1):41-8
pubmed: 9009236
J Med Chem. 2015 Oct 8;58(19):7634-58
pubmed: 25992880
Org Biomol Chem. 2007 Sep 21;5(18):2940-52
pubmed: 17728860
Expert Rev Anticancer Ther. 2011 Feb;11(2):179-83
pubmed: 21342037
J Enzyme Inhib Med Chem. 2018 Dec;33(1):1271-1282
pubmed: 30230387
Endocr Rev. 2005 Apr;26(2):171-202
pubmed: 15561802
Chem Biol Drug Des. 2016 Feb;87(2):233-8
pubmed: 26280898
Mol Cell Endocrinol. 2011 Jul 4;340(2):175-85
pubmed: 21238537
Invest New Drugs. 2015 Feb;33(1):95-103
pubmed: 25410727
Eur J Med Chem. 2019 Sep 1;177:116-143
pubmed: 31129450
Cancer Res. 1993 Jan 15;53(2):298-303
pubmed: 8417823
Cancer Res. 1996 Nov 1;56(21):4950-5
pubmed: 8895749
J Steroid Biochem Mol Biol. 2013 Sep;137:183-98
pubmed: 23391659
Eur J Med Chem. 2011 Sep;46(9):4227-37
pubmed: 21782294
J Med Chem. 2010 Apr 8;53(7):2942-51
pubmed: 20225862
Chem Rev. 2016 Jan 27;116(2):422-518
pubmed: 26756377
Nat Rev Drug Discov. 2004 Nov;3(11):935-49
pubmed: 15520816
Eur J Med Chem. 2017 Mar 10;128:79-87
pubmed: 28152429
Biochemistry. 1995 Sep 12;34(36):11508-14
pubmed: 7547880
Breast Cancer Res Treat. 2013 Jun 25;140(1):73-82
pubmed: 23797179
Biochim Biophys Acta. 2004 Jun 7;1654(2):123-43
pubmed: 15172700
PLoS One. 2013 Dec 06;8(12):e80305
pubmed: 24324595
Mini Rev Med Chem. 2016;16(17):1359-1373
pubmed: 27145849
J Clin Endocrinol Metab. 2002 Dec;87(12):5760-8
pubmed: 12466383
J Steroid Biochem Mol Biol. 2013 Sep;137:27-49
pubmed: 23291110
Cancer Res. 1997 Feb 15;57(4):702-7
pubmed: 9044848
Steroids. 2011 Sep-Oct;76(10-11):929-48
pubmed: 21458474
Bioorg Med Chem. 2016 Jun 15;24(12):2762-7
pubmed: 27143133
J Med Chem. 1998 Mar 26;41(7):1068-83
pubmed: 9544207
J Pak Med Assoc. 2013 Apr;63(4):509-15
pubmed: 23905452
Chem Biol. 2000 Oct;7(10):773-91
pubmed: 11033081
Cell Mol Life Sci. 2007 Aug;64(15):2013-22
pubmed: 17558559
Hum Reprod. 2011 Jun;26(6):1362-70
pubmed: 21441545
Reprod Sci. 2014 Oct;21(10):1256-65
pubmed: 24604234
Front Oncol. 2017 Mar 15;7:26
pubmed: 28361033
Eur J Med Chem. 2019 Nov 15;182:111614
pubmed: 31422224
J Med Chem. 2019 Jun 13;62(11):5512-5521
pubmed: 31062594
Bioorg Med Chem. 2017 Dec 15;25(24):6371-6378
pubmed: 29054710
ChemMedChem. 2013 May;8(5):779-99
pubmed: 23495205

Auteurs

Mateusz Daśko (M)

Department of Inorganic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.

Sebastian Demkowicz (S)

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.

Karol Biernacki (K)

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.

Olga Ciupak (O)

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.

Witold Kozak (W)

Department of Physical Chemistry, Faculty of Chemistry, University of Gdansk, Gdansk, Poland.

Maciej Masłyk (M)

Department of Molecular Biology, Faculty of Biotechnology and Environment Sciences, The John Paul II Catholic University of Lublin, Lublin, Poland.

Janusz Rachon (J)

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.

Articles similaires

[Redispensing of expensive oral anticancer medicines: a practical application].

Lisanne N van Merendonk, Kübra Akgöl, Bastiaan Nuijen
1.00
Humans Antineoplastic Agents Administration, Oral Drug Costs Counterfeit Drugs

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female
Humans United States Aged Cross-Sectional Studies Medicare Part C
1.00
Humans Yoga Low Back Pain Female Male

Classifications MeSH