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Synthesis, characterization and evaluation of antiproliferative activity of diisopropylphenyl esters of fatty acids from selected oils

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Abstract

The present investigation describes the synthesis, characterization and evaluation of antiproliferative activity of novel diisopropylphenol (propofol) conjugates of fatty acids. The fatty acids were obtained from oils of Jatropha curcas (jatropha) and Pongamia glabra (karanja) containing unsaturated-rich fatty acids, Sterculia foetida (containing cyclopropene-rich fatty acids), Samia cynthia (eri pupae, containing polyunsaturated-rich fatty acid, 18:3) and Cocos nucifera (coconut, containing medium-chain saturated-rich fatty acids). The synthesized conjugates viz. propofol-jatropha mixed fatty acid conjugates (2,4P-JTA and 2,6P-JTA), propofol-karanja mixed fatty acid conjugates (2,4P-KTA and 2,6P-KTA), propofol-sterculia foetida mixed fatty acid conjugates (2,4P-STA and 2,6P-STA), propofol-eri pupal mixed fatty acid conjugates (2,4P-EFA and 2,6-EFA) and propofol-coconut mixed fatty acid conjugates (2,4P-CCFA and 2,6P-CCFA) were obtained by esterification of the fatty acid mixture to propofol isomers (2,4-diisopropylphenol and 2,6-diisopropylphenol). The prepared derivatives were characterized by FT-IR, NMR (1H, 13C) and GC–MS and were tested for in vitro antiproliferative studies on A549, MDA-MB-231, HeLa, Mia-Pa–Ca and HePG2 cancer cell lines. All the synthesized propofol-mixed fatty acid conjugates showed good to moderate specific growth inhibition of cancer cells on studied cell lines. The results suggest that all the novel propofol-mixed fatty acid conjugates possess antiproliferative properties that reduce the proliferation of cancer cells in vitro.

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Acknowledgments

One of the authors SR gratefully acknowledges the Department of Biotechnology, New Delhi, for the financial assistance under sponsored project and Director, CSIR-IICT, for providing the facilities.

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Authors and Affiliations

  1. Centre for Lipid Research, CSIR‐Indian Institute of Chemical Technology (CSIR‐IICT), Hyderabad, 500007, Telangana, India

    Sathyam Reddy Yasa, Shiva Shanker Kaki & Vijayalakshmi Penumarthy

  2. Centre for Chemical Biology, CSIR‐Indian Institute of Chemical Technology (CSIR‐IICT), Hyderabad, 500007, Telangana, India

    Bala Bhaskara Rao & Nishant Jain

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  1. Sathyam Reddy Yasa
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  2. Shiva Shanker Kaki
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  3. Bala Bhaskara Rao
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  4. Nishant Jain
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  5. Vijayalakshmi Penumarthy
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Correspondence to Vijayalakshmi Penumarthy.

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Yasa, S.R., Kaki, S.S., Rao, B.B. et al. Synthesis, characterization and evaluation of antiproliferative activity of diisopropylphenyl esters of fatty acids from selected oils. Med Chem Res 25, 1299–1307 (2016). https://doi.org/10.1007/s00044-016-1564-4

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  • DOI: https://doi.org/10.1007/s00044-016-1564-4

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