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The impact of sugar and fatty acid on the bioactivity of N-fatty acyl-L-tyrosine aglycone

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Abstract

In the present study, a series of fatty acids-based (short, medium and long unsaturated chains) glycosylated N-fatty acyl-L-tyrosines and N-lipoyl-L-tyrosine methyl esters were synthesized and evaluated for their cytotoxic and antimicrobial activities. The aglycone moiety was synthesized using different chemical reagents. The glycosylation of aglycone moiety with different carbohydrates was performed using the Lewis acid, \(\hbox {BF}_{3.}\hbox {Et}_{2}\hbox {O}\). All the synthesized compounds were tested against a panel of four cancer cell lines. The glycosylated N-fatty acyl-L-tyrosines showed moderate activity against all the cell lines and the \(\hbox {IC}_{50}\) values were in the range of \(15.6{-}45.6\;{\upmu }\hbox {M}\). However, the oleic acid analogues (10a, 10d) exhibited \(\hbox {IC}_{50}\) values of 15.6, \(17.6\;{\upmu }\hbox {M}\), respectively, against MDA-MB-231 cell line. Glycosylated N-lipoyl-L-tyrosine methyl esters (6b–6d) showed promising activity against all the tested cell lines and the \(\hbox {IC}_{50}\) values ranged between \(9.4{-}13.8\;{\upmu }\hbox {M}\). The compound 6d exhibited significant cytotoxicity and \(\hbox {IC}_{50}\) values were 10.5, 9.4, 10.9 and \(12.1\;{\upmu }\hbox {M}\) against A549, PC3, MDA-MB-231 and HepG2 cell lines, respectively. Moreover, the non-glycosylated N-fatty acyl-L-tyrosine and methyl N-fatty acyl-L-tyrosinate derivatives showed excellent and moderate antimicrobial activity against some of the tested bacterial strains.

Graphical Abstract

The glycosylated N-fatty acyl-L-tyrosines with short, medium and long chain unsaturated fatty acids and glycosylated N-lipoyl-L-tyrosine methyl esters were synthesized and further evaluated for their biological activities to examine the impact of sugar and fatty acid on the bioactivity of N-fatty acyl-L-tyrosine derivatives.

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Acknowledgements

VS and YP acknowledge the Council of Scientific and Industrial Research, Government of India for financial support in the form of Fellowships.

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Authors and Affiliations

  1. Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, 500 007, India

    Srikanth Vudhgiri, R B N Prasad, E Anjaneyulu & Ram Chandra Reddy Jala

  2. Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, 500 007, India

    Y Poornachandra, C Ganesh Kumar & K Sirisha

  3. Academy of Scientific and Innovative Research, New Delhi, India

    Srikanth Vudhgiri, R B N Prasad, Y Poornachandra, C Ganesh Kumar, K Sirisha & Ram Chandra Reddy Jala

Authors
  1. Srikanth Vudhgiri
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  2. R B N Prasad
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  3. Y Poornachandra
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  4. C Ganesh Kumar
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  5. E Anjaneyulu
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  6. K Sirisha
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  7. Ram Chandra Reddy Jala
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Correspondence to Ram Chandra Reddy Jala.

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Vudhgiri, S., Prasad, R.B.N., Poornachandra, Y. et al. The impact of sugar and fatty acid on the bioactivity of N-fatty acyl-L-tyrosine aglycone. J Chem Sci 129, 663–677 (2017). https://doi.org/10.1007/s12039-017-1298-y

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  • DOI: https://doi.org/10.1007/s12039-017-1298-y

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