Structural modification of the aryl sulfonate ester of cjoc42 for enhanced gankyrin binding and anti-cancer activity

[Display omitted] Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in certain cancers results in an increase of gankyrin-mediated protein-protein interactions (PPIs), leading to cancer proliferation. To date, onl...

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Published inBioorganic & medicinal chemistry letters Vol. 30; no. 4; pp. 126889 - 126893
Main Authors Kanabar, Dipti, Farrales, Pamela, Gnanamony, Manu, Almasri, Joseph, Abo-Ali, Ehab M., Otmankel, Younos, Shah, Henna, Nguyen, Dawn, El Menyewi, Mark, Dukhande, Vikas V., D'Souza, Amber, Muth, Aaron
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.02.2020
Elsevier
Subjects
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiproliferation
Benzenesulfonates - chemical synthesis
Benzenesulfonates - chemistry
Benzenesulfonates - pharmacology
Binding Sites
Cell Line, Tumor
Cell Proliferation - drug effects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Esters - chemistry
Gankyrin
Humans
Life Sciences & Biomedicine
Liver cancer
Molecular Docking Simulation
Pharmacology & Pharmacy
Physical Sciences
Proteasome Endopeptidase Complex - metabolism
Protein Binding
Protein Structure, Tertiary
Protein–protein interactions
Proto-Oncogene Proteins - antagonists & inhibitors
Proto-Oncogene Proteins - metabolism
Science & Technology
Sulfonic Acids - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
Triazoles - pharmacology
Antiproliferation
Liver cancer
Protein–protein interactions
Gankyrin
PROTEIN
P28(GANK)
ONCOPROTEIN GANKYRIN
Protein-protein interactions
DISCOVERY
RB
C/EBP-ALPHA
S6 ATPASE
DEGRADATION
EXPRESSION
TUMORIGENESIS
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Abstract [Display omitted] Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in certain cancers results in an increase of gankyrin-mediated protein-protein interactions (PPIs), leading to cancer proliferation. To date, only one small molecule (cjoc42) has been identified to bind gankyrin, which simultaneously inhibits its interaction with the 26S proteasome. Despite this advance, 2nd generation inhibitors are needed to improve gankyrin binding and cellular efficacy. To this end, an extensive SAR for the aryl sulfonate ester moiety of the cjoc42 scaffold was explored, and showed that substitutions at the 2-, 3-, and 4-positions manifested significant increases in gankyrin binding, resulting in the most potent binders of gankyrin to date. Subsequent cell-based assay evaluation of our derivatives demonstrated antiproliferative activity against pediatric liver cancer cell lines Hep3B and HepG2, which was not previously observed for cjoc42.
AbstractList [Display omitted] Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in certain cancers results in an increase of gankyrin-mediated protein-protein interactions (PPIs), leading to cancer proliferation. To date, only one small molecule (cjoc42) has been identified to bind gankyrin, which simultaneously inhibits its interaction with the 26S proteasome. Despite this advance, 2nd generation inhibitors are needed to improve gankyrin binding and cellular efficacy. To this end, an extensive SAR for the aryl sulfonate ester moiety of the cjoc42 scaffold was explored, and showed that substitutions at the 2-, 3-, and 4-positions manifested significant increases in gankyrin binding, resulting in the most potent binders of gankyrin to date. Subsequent cell-based assay evaluation of our derivatives demonstrated antiproliferative activity against pediatric liver cancer cell lines Hep3B and HepG2, which was not previously observed for cjoc42.
Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in certain cancers results in an increase of gankyrin-mediated protein-protein interactions (PPIs), leading to cancer proliferation. To date, only one small molecule (cjoc42) has been identified to bind gankyrin, which simultaneously inhibits its interaction with the 26S proteasome. Despite this advance, 2nd generation inhibitors are needed to improve gankyrin binding and cellular efficacy. To this end, an extensive SAR for the aryl sulfonate ester moiety of the cjoc42 scaffold was explored, and showed that substitutions at the 2-, 3-, and 4-positions manifested significant increases in gankyrin binding, resulting in the most potent binders of gankyrin to date. Subsequent cell-based assay evaluation of our derivatives demonstrated antiproliferative activity against pediatric liver cancer cell lines Hep3B and HepG2, which was not previously observed for cjoc42.
ArticleNumber 126889
Author Otmankel, Younos
Gnanamony, Manu
Shah, Henna
Nguyen, Dawn
El Menyewi, Mark
D'Souza, Amber
Muth, Aaron
Kanabar, Dipti
Almasri, Joseph
Abo-Ali, Ehab M.
Farrales, Pamela
Dukhande, Vikas V.
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  surname: El Menyewi
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– sequence: 11
  givenname: Amber
  surname: D'Souza
  fullname: D'Souza, Amber
  organization: Department of Pediatrics, Hematology and Oncology, University of Illinois College of Medicine Peoria, Peoria, IL 61605, USA
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  givenname: Aaron
  orcidid: 0000-0002-9288-715X
  surname: Muth
  fullname: Muth, Aaron
  email: mutha@stjohns.edu
  organization: Department of Pharmaceutical Sciences, College of Pharmacy and Health Sciences, St. John’s University, Queens, NY 11439, USA
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Issue 4
Keywords Antiproliferation
Liver cancer
Protein–protein interactions
Gankyrin
PROTEIN
P28(GANK)
ONCOPROTEIN GANKYRIN
Protein-protein interactions
DISCOVERY
RB
C/EBP-ALPHA
S6 ATPASE
DEGRADATION
EXPRESSION
TUMORIGENESIS
Language English
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Publisher Elsevier Ltd
Elsevier
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Snippet [Display omitted] Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in...
Gankyrin is an oncogenic protein involved in various biological processes, such as cellular growth and proliferation. Its overexpression in certain cancers...
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StartPage 126889
SubjectTerms Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiproliferation
Benzenesulfonates - chemical synthesis
Benzenesulfonates - chemistry
Benzenesulfonates - pharmacology
Binding Sites
Cell Line, Tumor
Cell Proliferation - drug effects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Esters - chemistry
Gankyrin
Humans
Life Sciences & Biomedicine
Liver cancer
Molecular Docking Simulation
Pharmacology & Pharmacy
Physical Sciences
Proteasome Endopeptidase Complex - metabolism
Protein Binding
Protein Structure, Tertiary
Protein–protein interactions
Proto-Oncogene Proteins - antagonists & inhibitors
Proto-Oncogene Proteins - metabolism
Science & Technology
Sulfonic Acids - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
Triazoles - pharmacology
Title Structural modification of the aryl sulfonate ester of cjoc42 for enhanced gankyrin binding and anti-cancer activity
URI https://dx.doi.org/10.1016/j.bmcl.2019.126889
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https://www.ncbi.nlm.nih.gov/pubmed/31902711
Volume 30
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