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Design, synthesis, and biological evaluation of N-acetyl-S-(p-chlorophenylcarbamoyl)cysteine and its analogs as a novel class of anticancer agents

N-Acetyl-S-(p-chlorophenylcarbamoyl)cysteine (NACC) was identified as a metabolite of sulofenur. Sulofenur was demonstrated to have broad activity against solid tumors in preclinical studies but exhibited disappointing clinical responses due to its high protein binding related adverse effects. NACC... Full description

Journal Title: Bioorganic & Medicinal Chemistry 1 January 2011, Vol.19(1), pp.287-294
Main Author: Chen, Wei
Other Authors: Seefeldt, Teresa , Young, Alan , Zhang, Xiaoying , Guan, Xiangming
Format: Electronic Article Electronic Article
Language: English
Subjects:
Tfa
BSA
Fbs
Ewg
Edg
NAC
Mtt
PBS
PI
PS
Thf
ID: ISSN: 0968-0896 ; DOI: 10.1016/j.bmc.2010.11.026
Link: http://dx.doi.org/10.1016/j.bmc.2010.11.026
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recordid: sciversesciencedirect_elsevierS0968-0896(10)01039-4
title: Design, synthesis, and biological evaluation of N-acetyl-S-(p-chlorophenylcarbamoyl)cysteine and its analogs as a novel class of anticancer agents
format: Article
creator:
  • Chen, Wei
  • Seefeldt, Teresa
  • Young, Alan
  • Zhang, Xiaoying
  • Guan, Xiangming
subjects:
  • Tfa
  • BSA
  • Fbs
  • Dmso
  • Dpbs
  • Ewg
  • Edg
  • Hplc
  • Ic 50
  • NAC
  • Mtt
  • PBS
  • PI
  • PS
  • Thf
  • Anticancer Activity
  • Apoptosis
  • Cell Cycle Distribution
  • Synthesis
  • Structure Activity Relationship
ispartof: Bioorganic & Medicinal Chemistry, 1 January 2011, Vol.19(1), pp.287-294
description: N-Acetyl-S-(p-chlorophenylcarbamoyl)cysteine (NACC) was identified as a metabolite of sulofenur. Sulofenur was demonstrated to have broad activity against solid tumors in preclinical studies but exhibited disappointing clinical responses due to its high protein binding related adverse effects. NACC exhibited low protein binding and excellent activity against a sulofenur sensitive human colon cancer cell line. In this study, analogs of NACC were synthesized and evaluated with four human cancer cell lines. Two of the NACC analogs showed excellent activity against two human melanoma cell lines, while NACC remains the most potent of the series. All three compounds were more potent than dacarbazine, which is used extensively in treating melanoma. NACC was shown to induce apoptosis without affecting the cell cycle. Further, NACC exhibited low toxicity against monkey kidney cells. The selective anticancer activity, low toxicity, an unknown yet but unique anticancer mechanism and ready obtainability through synthesis make NACC and its analogs promising anticancer agents.
language: eng
source:
identifier: ISSN: 0968-0896 ; DOI: 10.1016/j.bmc.2010.11.026
fulltext: fulltext
issn:
  • 09680896
  • 0968-0896
url: Link


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titleDesign, synthesis, and biological evaluation of N-acetyl-S-(p-chlorophenylcarbamoyl)cysteine and its analogs as a novel class of anticancer agents
creatorChen, Wei ; Seefeldt, Teresa ; Young, Alan ; Zhang, Xiaoying ; Guan, Xiangming
ispartofBioorganic & Medicinal Chemistry, 1 January 2011, Vol.19(1), pp.287-294
identifierISSN: 0968-0896 ; DOI: 10.1016/j.bmc.2010.11.026
subjectTfa ; BSA ; Fbs ; Dmso ; Dpbs ; Ewg ; Edg ; Hplc ; Ic 50 ; NAC ; Mtt ; PBS ; PI ; PS ; Thf ; Anticancer Activity ; Apoptosis ; Cell Cycle Distribution ; Synthesis ; Structure Activity Relationship
descriptionN-Acetyl-S-(p-chlorophenylcarbamoyl)cysteine (NACC) was identified as a metabolite of sulofenur. Sulofenur was demonstrated to have broad activity against solid tumors in preclinical studies but exhibited disappointing clinical responses due to its high protein binding related adverse effects. NACC exhibited low protein binding and excellent activity against a sulofenur sensitive human colon cancer cell line. In this study, analogs of NACC were synthesized and evaluated with four human cancer cell lines. Two of the NACC analogs showed excellent activity against two human melanoma cell lines, while NACC remains the most potent of the series. All three compounds were more potent than dacarbazine, which is used extensively in treating melanoma. NACC was shown to induce apoptosis without affecting the cell cycle. Further, NACC exhibited low toxicity against monkey kidney cells. The selective anticancer activity, low toxicity, an unknown yet but unique anticancer mechanism and ready obtainability through synthesis make NACC and its analogs promising anticancer agents.
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abstractN-Acetyl-S-(p-chlorophenylcarbamoyl)cysteine (NACC) was identified as a metabolite of sulofenur. Sulofenur was demonstrated to have broad activity against solid tumors in preclinical studies but exhibited disappointing clinical responses due to its high protein binding related adverse effects. NACC exhibited low protein binding and excellent activity against a sulofenur sensitive human colon cancer cell line. In this study, analogs of NACC were synthesized and evaluated with four human cancer cell lines. Two of the NACC analogs showed excellent activity against two human melanoma cell lines, while NACC remains the most potent of the series. All three compounds were more potent than dacarbazine, which is used extensively in treating melanoma. NACC was shown to induce apoptosis without affecting the cell cycle. Further, NACC exhibited low toxicity against monkey kidney cells. The selective anticancer activity, low toxicity, an unknown yet but unique anticancer mechanism and ready obtainability through synthesis make NACC and its analogs promising anticancer agents.
pubElsevier Ltd
doi10.1016/j.bmc.2010.11.026
eissn14643391
date2011-01-01