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Structure−Activity Relationships of Diverse Annonaceous Acetogenins against Multidrug Resistant Human Mammary Adenocarcinoma (MCF-7/Adr) Cells
Abstract
Fourteen structurally diverse Annonaceous acetogenins, representing the three main classes of bis-adjacent, bis-nonadjacent, and single-THF ring(s), were tested for their ability to inhibit the growth of adriamycin resistant human mammary adenocarcinoma (MCF-7/Adr) cells. This cell line is resistant to treatment with adriamycin, vincristine, and vinblastine and is, thus, multidrug resistant (MDR). Among a series of bis-adjacent THF ring acetogenins, those with the stereochemistry of threo-trans-threo-trans-erythro (from C-15 to C-24) were the most potent with as much as 250 times the potency of adriamycin. A spacing of 13 carbons between the flanking hydroxyl of the THF ring system and the gamma-unsaturated lactone seems to be optimum with a spacing of 11 and 9 carbons being significantly less active. Several single-THF ring compounds were also quite potent with gigantetrocin A (11) being the most potent compound tested. The acetogenins may, thus, have chemotherapeutic potential, especially with regard to MDR tumors.
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Citations
Cited by
Annonaceous Acetogenins: Recent Progress
Alali, F. Q., Liu, X.-X., & McLaughlin, J. L. (1999) · Journal of Natural Products · doi:10.1021/np980406d · Cited by 818
Self-citationPaw Paw and Cancer: Annonaceous Acetogenins from Discovery to Commercial Products
McLaughlin, J. L. (2008) · Journal of Natural Products · doi:10.1021/np800191t · Cited by 294
Self-citationPotential Therapeutic Applications of the Genus Annona: Local and Traditional Uses and Pharmacology
Quílez, A. M., Fernández-Arche, M. A., García-Giménez, M. D., & De la Puerta, R. (2018) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2018.06.014 · Cited by 114
Nwokocha, C. R., Owu, D. U., Gordon, A., Thaxter, K., McCalla, G., Ozolua, R. I., & Young, L. (2012) · Pharmaceutical Biology · doi:10.3109/13880209.2012.684690 · Cited by 57
Anti hyperglycemic activities of Annona muricata (Linn)
Aderibigbe, K., Komolafe, O., Adewole, O., Obuotor, E., & Adenowo, T. (2010) · African Journal of Traditional, Complementary and Alternative Medicines · doi:10.4314/ajtcam.v6i1.57075 · Cited by 54
Metadata
- Authors
- Oberlies, N. H., Chang, C.-J., & McLaughlin, J. L.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-06-01
- Volume
- 40
- Issue
- 13
- Pages
- 2102-2106
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2083306481
- Cited by
- 178
- References
- 0
- FWCI
- 7.30
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Structure−Activity Relationships of Diverse Annonaceous Acetogenins against Multidrug Resistant Human Mammary Adenocarcinoma (MCF-7/Adr) Cells. https://app.cochat.ai/papers/10.1021/jm9700169
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- Oberlies, N. H., Chang, C.-J., & McLaughlin, J. L. (1997). Structure−Activity Relationships of Diverse Annonaceous Acetogenins against Multidrug Resistant Human Mammary Adenocarcinoma (MCF-7/Adr) Cells. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm9700169
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