Data di Pubblicazione:
2024
Citazione:
A Practical, Scalable Synthesis of 1,18‐Octadecanedioic acid‐Paclitaxel (ODDA‐PTX) / V. Rositano, A. Gambini, P. Allegrini, A. Bernardi, L. Senaldi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2024:(2024). [Epub ahead of print] [10.1002/ejoc.202301211]
Abstract:
Paclitaxel is one of the most important chemotherapy agents and it has shown activity against a variety of human cancers. In the past years several derivatives and formulations have been developed to improve its activity and reduce its toxicity. Recently, 1,18-Octadecanedioic acid-Paclitaxel (ODDA-PTX), obtained by conjugation of Paclitaxel with a long-chain diacid, has emerged as a promising Paclitaxel prodrug, with high efficacy and low toxicity. A novel strategy for its synthesis has been developed and is herein described. The approach is based on the mono-allyl protection of octadecanedioic acid (ODDA) and on the Pd-catalyzed removal of the allyl ester after coupling with Paclitaxel. This strategy is superior to previously reported procedures in that it affords the ODDA-PTX product with much higher purity, avoids chromatographic purifications and can be practically scaled-up for the industrial production of ODDA-PTX.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Taxol; Paclitaxel; regioselectivity; prodrugs; separation science; octadecanedioic acid monoester
Elenco autori:
V. Rositano, A. Gambini, P. Allegrini, A. Bernardi, L. Senaldi
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