Novel Alkynylphosphonate Analogue of Calcitriol with Potent Antiproliferative Effects in Cancer Cells and Lack of Calcemic Activity

Here, we describe the design and synthesis of diethyl [(5Z,7E)-(1S,3R)-1,3- dihydroxy-9,10-secochola-5,7,10(19)-trien-23-in-24-yl] phosphonate (compound 10), which combines the low calcemic properties of phosphonates with the decreased metabolic inactivation due to the presence of a triple bond in C...

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Bibliographic Details
Authors: Salomón, Débora Gisele, Grioli, Silvina Mariela, Buschiazzo, Maximiliano, Mascaro, Evangelina, Vitale, Cristian Alejandro, Radivoy, Gabriel Eduardo, Perez, Manuel, Fall, Yagamare, Mesri, Enrique Alfredo, Curino, Alejandro Carlos, Facchinetti, Maria Marta
Format: article
Status:Published version
Publication Date:2011
Country:Argentina
Institution:Consejo Nacional de Investigaciones Científicas y Técnicas
Repository:CONICET Digital (CONICET)
Language:English
OAI Identifier:oai:ri.conicet.gov.ar:11336/224479
Online Access:http://hdl.handle.net/11336/224479
Access Level:Open access
Keyword:1Α,25-(OH) 2 VITAMIN D 3
ALKYNYLPHOSPHONATE ANALOGUES
CANCER
CELLULAR PROLIFERATION
HYPERCALCEMIA
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Description
Summary:Here, we describe the design and synthesis of diethyl [(5Z,7E)-(1S,3R)-1,3- dihydroxy-9,10-secochola-5,7,10(19)-trien-23-in-24-yl] phosphonate (compound 10), which combines the low calcemic properties of phosphonates with the decreased metabolic inactivation due to the presence of a triple bond in C-24 and studied its in vitro effects on several cancer cell lines and its in vivo effects on blood calcium levels. We demonstrate that this compound is a potent antiproliferative vitamin D analogue, showing lack of calcemic effects in vivo.

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