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Synthesis and biological evaluation of prodigiosene conjugates of porphyrin, estrone and 4-hydroxytamoxifen.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2013 Oct 01; Vol. 21 (19), pp. 5995-6002. Date of Electronic Publication: 2013 Jul 31. - Publication Year :
- 2013
-
Abstract
- To generate the first series of prodigiosene conjugates, the tripyrrolic skeleton was appended to estrone, tamoxifen and porphyrin frameworks by way of ester linkers and various hydrocarbon chain lengths. The ability of the conjugates to inhibit various types of cancer cells was evaluated in vitro. The porphyrin conjugates did not exhibit significant activity. The estrone conjugates exhibited modest activity, for the most part. However, significantly greater growth inhibition activity against certain breast, colon, lung, leukemia, melanoma and prostate cell lines was noted. This unusual effect for this first generation model class of compound warrants further investigation and comparison to cases where estrogens are linked to prodigiosenes via connection points that do not feature in estrogen receptor binding. The 4-hydroxytamoxifen conjugates exhibit nanomolar range activity against the MCF-7 breast cancer cell line, paving the way to expand the scope and connectivity of prodigiosene-tamoxifen conjugates.<br /> (Copyright © 2013 Elsevier Ltd. All rights reserved.)
- Subjects :
- Cell Line, Tumor
Cell Proliferation drug effects
Cell Survival drug effects
Estrone chemistry
Estrone pharmacology
Humans
MCF-7 Cells
Molecular Structure
Tamoxifen chemistry
Estrone chemical synthesis
Neoplasms drug therapy
Porphyrins chemistry
Prodigiosin chemistry
Tamoxifen analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3391
- Volume :
- 21
- Issue :
- 19
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 23958515
- Full Text :
- https://doi.org/10.1016/j.bmc.2013.07.042