Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines.

@article{Mollica2014SynthesisAA,
  title={Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines.},
  author={Adriano Mollica and Roberto Costante and Serena Fiorito and Salvatore Genovese and Azzurra Stefanucci and V{\'e}ronique Mathieu and Robert Kiss and Francesco Epifano},
  journal={Fitoterapia},
  year={2014},
  volume={98},
  pages={
          91-7
        }
}
Three naturally occurring oxyprenylated diketopiperazines were synthesized and preliminarily tested as growth inhibitory agents in vitro against various cancer cell lines. The compounds were tested on six human cancer cell lines with different sensitivity to proapoptotic stimuli using the MTT colorimetric assay. The data revealed that of the chemicals under study only deoxymicelianamide (11) displayed the highest activity, recording mean IC50 growth inhibitory values ranging from 2 to 23 μM. A… 
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References

SHOWING 1-10 OF 21 REFERENCES
Design and synthesis of novel soluble 2,5-diketopiperazine derivatives as potential anticancer agents.
TLDR
Among allyl-protected derivatives, compound 4m had strong activity to all the cell lines, especially to the cancer cell lines U937 and K562, and could become a lead compound for further development for anticancer agents.
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
TLDR
Compounds 20 (4,2',4'-trihydroxychalcone), and 30 and 31 (two cinnamaldehydes) were cytostatic and able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli.
2,5-diketopiperazines as neuroprotective agents.
TLDR
An overview of the two major classes of diketopiperazines, the TRH-related and the unsaturated derivatives both characterized by a significant ability to protect against neurotoxicity in several experimental models is provided.
Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. II. Structural determination and total synthesis.
The structure of neihumicin, a new antibiotic isolated from the fermentation broth of Micromonospora neihuensis Wu, sp. nov., has been determined as
Structure and synthesis of phomamide, a new piperazine-2,5-dione related to the sirodesmins, isolated from the culture medium of Phoma lingam Tode
Several active substances are produced by the fungus Phoma lingam Tode, among which are the previously reported sirodesmins PL (1) and (2), sulphur-containing piperazinediones. A new metabolite,
Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein
TLDR
It is demonstrated that prenylation often found in plant secondary metabolism differentially modifies estrogenic properties of PEs depending on the basic structure of the respective PE.
Antimicrobial and biofilm inhibiting diketopiperazines.
TLDR
The potential of diketopiperazines in the clinic to erase biofilm infections will be discussed, with a special focus on the activity-toxicity problem of many compounds setting tight limitations to their application as drugs.
Enzymatic conversion of cyclic dipeptides to dehydro derivatives that inhibit cell division.
TLDR
Findings indicate that dehydrogenation at the alpha,beta-positions of both amino acid residues in this type of cyclic dipeptide is required for the inhibitory activity.
Biological active analogues of the opioid peptide biphalin: mixed α/β(3)-peptides.
TLDR
The derivative 1 containing hβ(3) Phe in place of Phe showed good μ- and δ-receptor affinities and antinociceptive activity in vivo together with an increased enzymatic stability in human plasma.
The sodium pump α1 sub-unit: a disease progression–related target for metastatic melanoma treatment
TLDR
The data show that all investigated human melanoma cell lines expressed high levels of the α1 sub‐unit, and 33% of human melanomas displayed significant α1Sub‐unit expression in correlation with the Breslow index, and cardenolides (notably UNBS1450; currently in Phase I clinical trials) displayed marked anti‐tumour effects against melanomas in vitro.
...
1
2
3
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