TY  - JOUR
AU  - Đokić, S.
AU  - Francuz, J.
AU  - Popsavin, M.
AU  - Rodić, M.V.
AU  - Kojić, V.
AU  - Stevanović, Milena
AU  - Popsavin, V.
PY  - 2022
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1546
AB  - Synthesis of protulactone A (PLA, 1) and twelve of its analogues have been achieved starting from D-galactose. PLA was isolated in the crystalline state, and its crystal structure was determined utilizing X-ray crystallography, which confirmed the assumed stereochemistry at all stereocenters. All tested compounds displayed antiproliferative activity against a panel of tumour cell lines, and all of them were non-cytotoxic toward the normal cells (MRC-5). Natural product PLA (1) was the most active against the K562 and MCF-7 cell lines (IC50 6.52 and 2.20 μM, respectively). Some of the synthesized derivatives showed very potent cytotoxicity, especially analogues 11, 13 and 15 (IC50 1.08–1.14 μM against MCF-7), and 9 and 14 (IC50 1.29 and 1.64 μM against K562). SAR analysis indicated important structural motifs for antiproliferative activity. Unfortunately, PLA (1), its C-7 epimer (2) and demethylated analogue (3) did not display a significant antimicrobial activity (two Gram-positive and two Gram-negative bacteria and one fungal strain) and they also cannot affect the ability to modulate bacterial communication.
PB  - Academic Press Inc.
T2  - Bioorganic Chemistry
T1  - Natural product protulactone A: Total synthesis from D-galactose, X-ray analysis and biological evaluation
VL  - 127
DO  - 10.1016/j.bioorg.2022.105980
ER  - 

@article{
author = "Đokić, S. and Francuz, J. and Popsavin, M. and Rodić, M.V. and Kojić, V. and Stevanović, Milena and Popsavin, V.",
year = "2022",
abstract = "Synthesis of protulactone A (PLA, 1) and twelve of its analogues have been achieved starting from D-galactose. PLA was isolated in the crystalline state, and its crystal structure was determined utilizing X-ray crystallography, which confirmed the assumed stereochemistry at all stereocenters. All tested compounds displayed antiproliferative activity against a panel of tumour cell lines, and all of them were non-cytotoxic toward the normal cells (MRC-5). Natural product PLA (1) was the most active against the K562 and MCF-7 cell lines (IC50 6.52 and 2.20 μM, respectively). Some of the synthesized derivatives showed very potent cytotoxicity, especially analogues 11, 13 and 15 (IC50 1.08–1.14 μM against MCF-7), and 9 and 14 (IC50 1.29 and 1.64 μM against K562). SAR analysis indicated important structural motifs for antiproliferative activity. Unfortunately, PLA (1), its C-7 epimer (2) and demethylated analogue (3) did not display a significant antimicrobial activity (two Gram-positive and two Gram-negative bacteria and one fungal strain) and they also cannot affect the ability to modulate bacterial communication.",
publisher = "Academic Press Inc.",
journal = "Bioorganic Chemistry",
title = "Natural product protulactone A: Total synthesis from D-galactose, X-ray analysis and biological evaluation",
volume = "127",
doi = "10.1016/j.bioorg.2022.105980"
}

Đokić, S., Francuz, J., Popsavin, M., Rodić, M.V., Kojić, V., Stevanović, M.,& Popsavin, V.. (2022). Natural product protulactone A: Total synthesis from D-galactose, X-ray analysis and biological evaluation. in Bioorganic Chemistry
Academic Press Inc.., 127.
https://doi.org/10.1016/j.bioorg.2022.105980

Đokić S, Francuz J, Popsavin M, Rodić M, Kojić V, Stevanović M, Popsavin V. Natural product protulactone A: Total synthesis from D-galactose, X-ray analysis and biological evaluation. in Bioorganic Chemistry. 2022;127.
doi:10.1016/j.bioorg.2022.105980 .

Đokić, S., Francuz, J., Popsavin, M., Rodić, M.V., Kojić, V., Stevanović, Milena, Popsavin, V., "Natural product protulactone A: Total synthesis from D-galactose, X-ray analysis and biological evaluation" in Bioorganic Chemistry, 127 (2022),
https://doi.org/10.1016/j.bioorg.2022.105980 . .