A-ring-fused pyrazoles of dihydrotestosterone targeting prostate cancer cells via the downregulation of the androgen receptor Article Swipe
Miroslav Peřina
,
Márton A. Kiss
,
Gergő Mótyán
,
Eva Szczyrbová
,
Martin Eliáš
,
Vladimír Študent
,
Daniela Kurfürstová
,
Markéta Kovalová
,
Lukáš Mada
,
Jan Bouchal
,
Éva Frank
,
Radek Jorda
·
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1101/2022.12.17.520850
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1101/2022.12.17.520850
High expression of the androgen receptor (AR) and the disruption of its regulation are strongly responsible for the development of prostate cancer (PCa). Therapeutically relevant non-steroidal or steroidal antiandrogens are able to block the AR effect by eliminating AR-mediated signalling. Herein we report the synthesis of novel steroidal pyrazoles derived from the natural sex hormone 5α-dihydrotestosterone (DHT). 2-Ethylidene or 2-(hetero)arylidene derivatives of DHT obtained by regioselective Claisen-Schmidt condensation with acetaldehyde or (hetero)aromatic aldehydes in alkaline ethanol were reacted with monosubstituted hydrazines to give A-ring-fused 1,5-disubstituted pyrazoles as main or exclusive products, depending on the reaction conditions applied. Spontaneous or 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)-induced oxidation of the primarily formed pyrazolines resulted in the desired products in moderate to good yields, while 17-oxidation also occurred by using the Jones reagent as a strong oxidant. Transcriptional activity of the AR in a reporter cell line was examined for all novel compounds, and several previously synthesized similar DHT-based pyrazoles with differently substituted heteroring were also included to obtain information about the structure-activity relationship. Two specific regioisomeric groups of derivatives significantly diminished the transcriptional activity of AR in reporter cell line in 10 μM concentration, and displayed reasonable antiproliferative activity in AR-positive PCa cell lines. Lead compound ( 3d ) was found to be a potent AR antagonist (IC 50 = 1.18 μM), generally suppressed AR signalling in time and dose dependent manner, moreover, it also led to a sharp decrease in wt-AR protein level probably caused by proteasomal degradation. We confirmed the antiproliferative activity selective for AR-positive PCa cell lines (with GI 50 in low micromolar ranges), cellular, biochemical and in silico binding of 3d in AR ligand-binding domain. Moreover, compound 3d was shown to be potent even ex vivo in patient-derived tissues, which highlights the therapeutic potential of A-ring-fused pyrazoles. Table of content graphic Highlights A-ring-fused pyrazoles of 5α-dihydrotestosterone were introduced as AR modulators SAR study of 55 differently substituted derivatives was discussed Compound 3d suppressed the expression of AR targets in prostate cell lines Compound 3d caused AR degradation in time-dependent manner Ex vivo activity of 3d was demonstrated in patient-derived explants
Related Topics
Concepts
Chemistry
Androgen receptor
Dihydrotestosterone
Downregulation and upregulation
Androgen
Prostate cancer
Cell culture
Ring (chemistry)
Stereochemistry
Internal medicine
Cancer
Biochemistry
Hormone
Biology
Organic chemistry
Medicine
Genetics
Gene
Metadata
- Type
- preprint
- Language
- en
- Landing Page
- https://doi.org/10.1101/2022.12.17.520850
- https://www.biorxiv.org/content/biorxiv/early/2022/12/19/2022.12.17.520850.full.pdf
- OA Status
- green
- Cited By
- 1
- References
- 34
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4313425242
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4313425242Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1101/2022.12.17.520850Digital Object Identifier
- Title
-
A-ring-fused pyrazoles of dihydrotestosterone targeting prostate cancer cells via the downregulation of the androgen receptorWork title
- Type
-
preprintOpenAlex work type
- Language
-
enPrimary language
- Publication year
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2022Year of publication
- Publication date
-
2022-12-19Full publication date if available
- Authors
-
Miroslav Peřina, Márton A. Kiss, Gergő Mótyán, Eva Szczyrbová, Martin Eliáš, Vladimír Študent, Daniela Kurfürstová, Markéta Kovalová, Lukáš Mada, Jan Bouchal, Éva Frank, Radek JordaList of authors in order
- Landing page
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https://doi.org/10.1101/2022.12.17.520850Publisher landing page
- PDF URL
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https://www.biorxiv.org/content/biorxiv/early/2022/12/19/2022.12.17.520850.full.pdfDirect link to full text PDF
- Open access
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YesWhether a free full text is available
- OA status
-
greenOpen access status per OpenAlex
- OA URL
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https://www.biorxiv.org/content/biorxiv/early/2022/12/19/2022.12.17.520850.full.pdfDirect OA link when available
- Concepts
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Chemistry, Androgen receptor, Dihydrotestosterone, Downregulation and upregulation, Androgen, Prostate cancer, Cell culture, Ring (chemistry), Stereochemistry, Internal medicine, Cancer, Biochemistry, Hormone, Biology, Organic chemistry, Medicine, Genetics, GeneTop concepts (fields/topics) attached by OpenAlex
- Cited by
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1Total citation count in OpenAlex
- Citations by year (recent)
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2024: 1Per-year citation counts (last 5 years)
- References (count)
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34Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.tissues, | 287 |
| abstract_inverted_index.DHT-based | 152 |
| abstract_inverted_index.Moreover, | 274 |
| abstract_inverted_index.aldehydes | 73 |
| abstract_inverted_index.cellular, | 262 |
| abstract_inverted_index.confirmed | 245 |
| abstract_inverted_index.dependent | 225 |
| abstract_inverted_index.depending | 92 |
| abstract_inverted_index.discussed | 318 |
| abstract_inverted_index.displayed | 190 |
| abstract_inverted_index.exclusive | 90 |
| abstract_inverted_index.generally | 217 |
| abstract_inverted_index.moreover, | 227 |
| abstract_inverted_index.oxidation | 102 |
| abstract_inverted_index.potential | 292 |
| abstract_inverted_index.primarily | 105 |
| abstract_inverted_index.products, | 91 |
| abstract_inverted_index.pyrazoles | 49, 86, 153, 302 |
| abstract_inverted_index.selective | 249 |
| abstract_inverted_index.steroidal | 28, 48 |
| abstract_inverted_index.synthesis | 45 |
| abstract_inverted_index.Highlights | 300 |
| abstract_inverted_index.antagonist | 211 |
| abstract_inverted_index.compounds, | 146 |
| abstract_inverted_index.conditions | 96 |
| abstract_inverted_index.diminished | 175 |
| abstract_inverted_index.disruption | 10 |
| abstract_inverted_index.expression | 2, 323 |
| abstract_inverted_index.heteroring | 157 |
| abstract_inverted_index.highlights | 289 |
| abstract_inverted_index.hydrazines | 81 |
| abstract_inverted_index.introduced | 306 |
| abstract_inverted_index.micromolar | 260 |
| abstract_inverted_index.modulators | 309 |
| abstract_inverted_index.previously | 149 |
| abstract_inverted_index.pyrazoles. | 295 |
| abstract_inverted_index.reasonable | 191 |
| abstract_inverted_index.regulation | 13 |
| abstract_inverted_index.signalling | 220 |
| abstract_inverted_index.suppressed | 218, 321 |
| abstract_inverted_index.AR-mediated | 39 |
| abstract_inverted_index.AR-positive | 195, 251 |
| abstract_inverted_index.Spontaneous | 98 |
| abstract_inverted_index.biochemical | 263 |
| abstract_inverted_index.degradation | 335 |
| abstract_inverted_index.derivatives | 61, 173, 316 |
| abstract_inverted_index.development | 19 |
| abstract_inverted_index.differently | 155, 314 |
| abstract_inverted_index.eliminating | 38 |
| abstract_inverted_index.information | 163 |
| abstract_inverted_index.proteasomal | 242 |
| abstract_inverted_index.pyrazolines | 107 |
| abstract_inverted_index.responsible | 16 |
| abstract_inverted_index.signalling. | 40 |
| abstract_inverted_index.substituted | 156, 315 |
| abstract_inverted_index.synthesized | 150 |
| abstract_inverted_index.therapeutic | 291 |
| abstract_inverted_index.17-oxidation | 119 |
| abstract_inverted_index.2-Ethylidene | 58 |
| abstract_inverted_index.A-ring-fused | 84, 294, 301 |
| abstract_inverted_index.acetaldehyde | 70 |
| abstract_inverted_index.condensation | 68 |
| abstract_inverted_index.degradation. | 243 |
| abstract_inverted_index.demonstrated | 345 |
| abstract_inverted_index.(DDQ)-induced | 101 |
| abstract_inverted_index.antiandrogens | 29 |
| abstract_inverted_index.non-steroidal | 26 |
| abstract_inverted_index.regioisomeric | 170 |
| abstract_inverted_index.relationship. | 167 |
| abstract_inverted_index.significantly | 174 |
| abstract_inverted_index.concentration, | 188 |
| abstract_inverted_index.ligand-binding | 272 |
| abstract_inverted_index.regioselective | 66 |
| abstract_inverted_index.time-dependent | 337 |
| abstract_inverted_index.Claisen-Schmidt | 67 |
| abstract_inverted_index.Therapeutically | 24 |
| abstract_inverted_index.Transcriptional | 131 |
| abstract_inverted_index.monosubstituted | 80 |
| abstract_inverted_index.patient-derived | 286, 347 |
| abstract_inverted_index.transcriptional | 177 |
| abstract_inverted_index.(hetero)aromatic | 72 |
| abstract_inverted_index.1,5-disubstituted | 85 |
| abstract_inverted_index.antiproliferative | 192, 247 |
| abstract_inverted_index.structure-activity | 166 |
| abstract_inverted_index.2-(hetero)arylidene | 60 |
| abstract_inverted_index.5α-dihydrotestosterone | 56, 304 |
| abstract_inverted_index.2,3-dichloro-5,6-dicyanobenzoquinone | 100 |
| cited_by_percentile_year.max | 94 |
| cited_by_percentile_year.min | 90 |
| corresponding_author_ids | https://openalex.org/A5057824431, https://openalex.org/A5062283022 |
| countries_distinct_count | 2 |
| institutions_distinct_count | 12 |
| corresponding_institution_ids | https://openalex.org/I227486990, https://openalex.org/I70703428 |
| sustainable_development_goals[0].id | https://metadata.un.org/sdg/3 |
| sustainable_development_goals[0].score | 0.7599999904632568 |
| sustainable_development_goals[0].display_name | Good health and well-being |
| citation_normalized_percentile.value | 0.62999082 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | False |