Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studiesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1dt10995b.
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| Title: | Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studiesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1dt10995b. |
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| Authors: | Vera, José1, Gao, Li Ming1, Santana, Alberto1, Matta, Jaime2, Meléndez, Enrique1 |
| Source: | Dalton Transactions: An International Journal of Inorganic Chemistry. Sep2011, Vol. 40 Issue 37, p9557-9565. 9p. |
| Subjects: | Ferrocene, Estrogen, Ergocalciferol, Biosynthesis, Cell-mediated cytotoxicity, Electrochemical analysis, Hydroxyl group, Hydrophobic surfaces |
| Abstract: | Three ferrocene complexes vectorized with estrogens and vitamin D2were synthesized and fully characterized by spectroscopic, electrochemical and computational methods. The synthesis of these esters was accomplished by reacting ferrocenoyl chloride with the corresponding ROH groups (R = ergocalciferol, estradiol, estrone). The cytotoxicity of these complexes in HT-29 colon cancer and MCF-7 breast cancer cell lines was investigated in vitro. Only ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate showed good cytotoxic activity in both cell lines, exceeding those of ferrocenium and ferrocene. In MCF-7, ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate exhibited remarkable IC50, in the low micromolar range. This may be attributed to the presence of the estradiol vector. Docking studies between alpha-estrogen receptor ligand binding site and ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate revealed some key hydrophobic interactions that might explain the cytotoxic activity of this ester. [ABSTRACT FROM AUTHOR] |
| Copyright of Dalton Transactions: An International Journal of Inorganic Chemistry is the property of Royal Society of Chemistry and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 65332636 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studiesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1dt10995b. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Vera%2C+José%22">Vera, José</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Gao%2C+Li+Ming%22">Gao, Li Ming</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Santana%2C+Alberto%22">Santana, Alberto</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Matta%2C+Jaime%22">Matta, Jaime</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Meléndez%2C+Enrique%22">Meléndez, Enrique</searchLink><relatesTo>1</relatesTo> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Dalton+Transactions%3A+An+International+Journal+of+Inorganic+Chemistry%22">Dalton Transactions: An International Journal of Inorganic Chemistry</searchLink>. Sep2011, Vol. 40 Issue 37, p9557-9565. 9p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Ferrocene%22">Ferrocene</searchLink><br /><searchLink fieldCode="DE" term="%22Estrogen%22">Estrogen</searchLink><br /><searchLink fieldCode="DE" term="%22Ergocalciferol%22">Ergocalciferol</searchLink><br /><searchLink fieldCode="DE" term="%22Biosynthesis%22">Biosynthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Cell-mediated+cytotoxicity%22">Cell-mediated cytotoxicity</searchLink><br /><searchLink fieldCode="DE" term="%22Electrochemical+analysis%22">Electrochemical analysis</searchLink><br /><searchLink fieldCode="DE" term="%22Hydroxyl+group%22">Hydroxyl group</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrophobic+surfaces%22">Hydrophobic surfaces</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: Three ferrocene complexes vectorized with estrogens and vitamin D2were synthesized and fully characterized by spectroscopic, electrochemical and computational methods. The synthesis of these esters was accomplished by reacting ferrocenoyl chloride with the corresponding ROH groups (R = ergocalciferol, estradiol, estrone). The cytotoxicity of these complexes in HT-29 colon cancer and MCF-7 breast cancer cell lines was investigated in vitro. Only ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate showed good cytotoxic activity in both cell lines, exceeding those of ferrocenium and ferrocene. In MCF-7, ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate exhibited remarkable IC50, in the low micromolar range. This may be attributed to the presence of the estradiol vector. Docking studies between alpha-estrogen receptor ligand binding site and ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate revealed some key hydrophobic interactions that might explain the cytotoxic activity of this ester. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Dalton Transactions: An International Journal of Inorganic Chemistry is the property of Royal Society of Chemistry and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1039/c1dt10995b Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 9 StartPage: 9557 Subjects: – SubjectFull: Ferrocene Type: general – SubjectFull: Estrogen Type: general – SubjectFull: Ergocalciferol Type: general – SubjectFull: Biosynthesis Type: general – SubjectFull: Cell-mediated cytotoxicity Type: general – SubjectFull: Electrochemical analysis Type: general – SubjectFull: Hydroxyl group Type: general – SubjectFull: Hydrophobic surfaces Type: general Titles: – TitleFull: Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studiesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1dt10995b. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Vera, José – PersonEntity: Name: NameFull: Gao, Li Ming – PersonEntity: Name: NameFull: Santana, Alberto – PersonEntity: Name: NameFull: Matta, Jaime – PersonEntity: Name: NameFull: Meléndez, Enrique IsPartOfRelationships: – BibEntity: Dates: – D: 08 M: 09 Text: Sep2011 Type: published Y: 2011 Identifiers: – Type: issn-print Value: 14779226 Numbering: – Type: volume Value: 40 – Type: issue Value: 37 Titles: – TitleFull: Dalton Transactions: An International Journal of Inorganic Chemistry Type: main |
| ResultId | 1 |
