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Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention

Synthesis of a novel theranostic molecule for targeted cancer intervention. A reaction between curcumin and lawsone was carried out to yield the novel curcumin naphthoquinone (CurNQ) molecule (2,2′-((((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl) bis(2-methoxy-4,1-phenylene))bis(oxy))bis(na...

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Autores principales: Freidus, Lara G., Kumar, Pradeep, Marimuthu, Thashree, Pradeep, Priyamvada, Pillay, Viness, Choonara, Yahya E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7582707/
https://www.ncbi.nlm.nih.gov/pubmed/33003358
http://dx.doi.org/10.3390/molecules25194471
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author Freidus, Lara G.
Kumar, Pradeep
Marimuthu, Thashree
Pradeep, Priyamvada
Pillay, Viness
Choonara, Yahya E.
author_facet Freidus, Lara G.
Kumar, Pradeep
Marimuthu, Thashree
Pradeep, Priyamvada
Pillay, Viness
Choonara, Yahya E.
author_sort Freidus, Lara G.
collection PubMed
description Synthesis of a novel theranostic molecule for targeted cancer intervention. A reaction between curcumin and lawsone was carried out to yield the novel curcumin naphthoquinone (CurNQ) molecule (2,2′-((((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl) bis(2-methoxy-4,1-phenylene))bis(oxy))bis(naphthalene-1,4-dione). CurNQ’s structure was elucidated and was fully characterized. CurNQ was demonstrated to have pH specific solubility, its saturation solubility increased from 11.15 µM at pH 7.4 to 20.7 µM at pH 6.8. This pH responsivity allows for cancer targeting (Warburg effect). Moreover, CurNQ displayed intrinsic fluorescence, thus enabling imaging and detection applications. In vitro cytotoxicity assays demonstrated the chemotherapeutic properties of CurNQ as CurNQ reduced cell viability to below 50% in OVCAR-5 and SKOV3 ovarian cancer cell lines. CurNQ is a novel theranostic molecule for potential targeted cancer detection and treatment.
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spelling pubmed-75827072020-10-28 Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention Freidus, Lara G. Kumar, Pradeep Marimuthu, Thashree Pradeep, Priyamvada Pillay, Viness Choonara, Yahya E. Molecules Article Synthesis of a novel theranostic molecule for targeted cancer intervention. A reaction between curcumin and lawsone was carried out to yield the novel curcumin naphthoquinone (CurNQ) molecule (2,2′-((((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl) bis(2-methoxy-4,1-phenylene))bis(oxy))bis(naphthalene-1,4-dione). CurNQ’s structure was elucidated and was fully characterized. CurNQ was demonstrated to have pH specific solubility, its saturation solubility increased from 11.15 µM at pH 7.4 to 20.7 µM at pH 6.8. This pH responsivity allows for cancer targeting (Warburg effect). Moreover, CurNQ displayed intrinsic fluorescence, thus enabling imaging and detection applications. In vitro cytotoxicity assays demonstrated the chemotherapeutic properties of CurNQ as CurNQ reduced cell viability to below 50% in OVCAR-5 and SKOV3 ovarian cancer cell lines. CurNQ is a novel theranostic molecule for potential targeted cancer detection and treatment. MDPI 2020-09-29 /pmc/articles/PMC7582707/ /pubmed/33003358 http://dx.doi.org/10.3390/molecules25194471 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Freidus, Lara G.
Kumar, Pradeep
Marimuthu, Thashree
Pradeep, Priyamvada
Pillay, Viness
Choonara, Yahya E.
Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention
title Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention
title_full Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention
title_fullStr Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention
title_full_unstemmed Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention
title_short Synthesis and Properties of CurNQ for the Theranostic Application in Ovarian Cancer Intervention
title_sort synthesis and properties of curnq for the theranostic application in ovarian cancer intervention
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7582707/
https://www.ncbi.nlm.nih.gov/pubmed/33003358
http://dx.doi.org/10.3390/molecules25194471
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