Synthesis of carbohydrate analogues of the THF-acetogenin 4-deoxyannomontacin and their cytotoxicity against human prostate cancer cell lines Journal Article

   


Authors: Gonzalez Periche, P.; Ramdular, A.; Bhupathiraju, N. V. S. D. K.; Kalidindi, T.; Johnson, D. S.; Pillarsetty, N.; Mootoo, D. R.
Article Title: Synthesis of carbohydrate analogues of the THF-acetogenin 4-deoxyannomontacin and their cytotoxicity against human prostate cancer cell lines
Abstract: The THF containing acetogenin 4-deoxyannonmontacin (4-DAN) has attracted interest for its potent cytotoxicity against a broad range of human tumor cell lines, and relatively simple structure. Herein is described the synthesis and cytotoxicity of C-10 epimers of 4-DAN and analogues thereof comprising carbohydrate and thiophene substitutes for the THF and butenolide moieties respectively. The key synthetic ploy was the union of THF and butenolide segments or their substitutes, via an alkene cross metathesis. The different analogues showed cytotoxicity in the low micromolar to nanomolar range against the human prostate cancer cell lines LNCaP and PC3. A relatively simple mannose-linked thiophene analog was found to be similar in activity to 4-DAN. © 2022
Keywords: controlled study; human cell; doxorubicin; antineoplastic agents; antineoplastic agent; cytotoxicity; cell line, tumor; drug synthesis; prostate cancer; prostatic neoplasms; chemistry; cell culture; prostate tumor; tumor cell line; urology; drug cytotoxicity; prostate cancers; diseases; carbohydrates; carbohydrate; carbohydrate derivative; gamma butyrolactone; 4-butyrolactone; cells; thiophene derivative; thiophenes; cancer cell lines; alkene; alkenes; human prostate cancer cells; mannose; humans; human; male; article; prostate cancer cell line; lncap cell line; pc-3 [human prostate carcinoma] cell line; 4-deoxyannomontacin; acetogenin; mimetic; thiophene; acetogenins; butenolides; epimers; human tumor cell lines; mimetics; simple structures; 4-deacetylneosolaniol; butenolide; trichothecene derivative; epimer; trichothecenes
Journal Title: Carbohydrate Research
Volume: 521
ISSN: 0008-6215
Publisher: Elsevier Science, Inc.  
Date Published: 2022-11-01
Start Page: 108671
Language: English
DOI: 10.1016/j.carres.2022.108671
PUBMED: 36113243
PROVIDER: scopus
PMCID: PMC10288172
DOI/URL:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85138824725&doi=10.1016%2fj.carres.2022.108671&partnerID=40&md5=c52c39b6a81e1d2f36ec82c7f0ac1d92
Notes: Article -- Export Date: 1 November 2022 -- Source: Scopus
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MSK Authors
  1. Nagavarakishore Pillarsetty
    136 Pillarsetty
  2. Teja Muralidhar Kalidindi
    41 Kalidindi
  3. Delissa Shaleel Johnson
    3 Johnson
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