The synthesis and anticancer activity of selected diketopiperazines

Merwe, E. van der; Huang, Dayong; Peterson, David S.; Kilian, Gareth; Milne, P. J.; Venter, Maryna van de; Frost, Carminita

doi:10.1016/j.peptides.2008.03.010

Cited by 54 publications

(22 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Because these molecules have antibacterial, anticancer, weeding, and antivirus features, they are potential drug candidates [6][7][8][9]. The cyclic peptide compounds have a wide range of biological activities such as anti-tumor, anti-HIV, anti-bacterial, anti-malaria have attracted more concern research on it [10].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of hexahydro-7-hydroxy-3-(2-methylpropyl)pyrrolo [1,2-a]pyrazine-1,4-dione, C11H18N2O3

Zhang

Lei

2015

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

Source of materialAntimicrobial cyclic dipeptides C6, a novel polyketide, was isolated from the metabolites of Streptomyces sp a soil sample. Strain was cultured for six day in a 5L fermenter in glycerol/corn meal medium (50 g L-1, glycerol, 25 gL-1corn meal, yeast extract 5 gL-1, pH 7.0 prior to sterilization) at 301(2) K, stirring at 200 rpm. The culture filtrate was separated by centrifugation from the mycelium and subjected to HP-20 resin. After washing with water, a crude product was obtained through elution with methanol. The eluate was concentrated in vaccuo and lyophilized. Then, the crude extract was separated by normal phase chromatography on silica gel (methanol). Next, the sample was purified by HPLC detection of high pressure reverse phase. Suitable single crystals of the title compound were obtained after one week by slow evaporation from methanol solution. Experimental detailsAll H atoms attached to C atoms and O atom were introduced using the HFIX command in the SHELXL-97 program [1]. N-H distance restrained to 0.86 Å with U iso = 1.2U eq (parent atom) and O-H distance restrained to 0.82 Å, the U iso values of the hydrogen atoms of methylene groups was set to 1.5U eq (C) and the U iso values of all other hydrogen atom were set to 1.2U eq (C, N,O) [2,3].The data collection with Cu-K a radiation yielded a completeness of 94.2 % (q max = 65.99°) only. DiscussionBiological activity of cyclic peptides [termed as 2,5-diketopiperazines] are ubiquitous in nature, and they represent the simplest and first fully characterized small peptides [4,5]. Because these molecules have antibacterial, anticancer, weeding, and antivirus features, they are potential drug candidates [6][7][8][9]. The cyclic peptide compounds have a wide range of biological activities such as anti-tumor, anti-HIV, anti-bacterial, anti-malaria have attracted more concern research on it [10]. However, the cyclic dipeptide C6 demonstrates activity against avian influenza [11]. The bond lengths and angles derived from the title structure, are within normal ranges. The O2-C5 and O3-C7 bond distances

show abstract

Section: Discussionmentioning

confidence: 99%

Crystal structure of hexahydro-7-hydroxy-3-(2-methylpropyl)pyrrolo [1,2-a]pyrazine-1,4-dione, C11H18N2O3

Zhang

Lei

2015

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

show abstract

“…The ground state geometry was calculated with all three versions of the Sparkle Model [22][23][24][25]. The calculations were carried out considering periodic bound conditions aiming to obtain a solid state structure [25].…”

Section: Structure Simulationmentioning

confidence: 99%

“…Sparkle/AM1 [22], Sparkle/PM3 [23] and Sparkle/PM6 [24] solid structure the X-ray diffraction simulations were performed. The structure obtained with the Sparkle/AM1 and PM6 models showed low level of agreement with the experimental result.…”

Section: Structure Simulation and Luminescence Spectroscopymentioning

confidence: 99%

Hydrothermal reactions: From the synthesis of ligand to new lanthanide 3D-coordination polymers

Silva

Oliveira

Falcão

et al. 2013

Journal of Solid State Chemistry

View full text Add to dashboard Cite

“…Cyclo(Gly-Val) has been reported to inhibit colon and cervical carcinoma cell lines, which may be a potential molecule in the treatment of cancer (van der Merwe et al 2008). It has an unsymmetrical structure.…”

Section: Cyclo(gly-val)mentioning

confidence: 99%

“…Due to its high sensitivity and selectivity, MS has been the most useful tool for analysis of cyclic dipeptides. A variety of ionization methods for analysis of cyclic peptides have been used including electron ionization (EI), photoionization (PI) (Ling and Lifshitz 1998), chemical ionization (CI) (Wabnitz et al 1996), fast atom bombardment (FAB) (van der Merwe et al 2008) and electrospray ionization (ESI) (Furtado et al 2007;Guo et al 2009a, b). The fragmentation pathways of protonated and deprotonated cyclic dipeptides have been studied by ESI-MS/MS (Furtado et al 2007;Guo et al 2009a, b;Wabnitz et al 1996).…”

Section: Introductionmentioning

confidence: 99%

Synchrotron vacuum ultraviolet (VUV) photo-induced fragmentation of cyclic dipeptides radical cations

et al. 2011

View full text Add to dashboard Cite

Cyclic dipeptides, due to their chemical properties and various bioactivities, are very attractive for medicinal chemistry. Fragmentations of three simple cyclic dipeptides including cyclo(Gly-Gly), cyclo(Ala-Ala) and cyclo(Gly-Val) in the gas-phase are determined with synchrotron vacuum ultraviolet (VUV) photoionization mass spectrometry (VUV PIMS) and theoretical calculations. Cyclo(Gly-Gly) and cyclo(Ala-Ala) show the similar fragmentation pathways. The primary decomposition reactions of cyclo(Gly-Gly) and cyclo(Ala-Ala) radical cations are found to be HNCO loss and CO elimination. The appearance energies (AEs) of fragment ions [CH2NHCOCH2]+• and [CH3CHNHCOCHCH3]+• are measured to be 10.21 and 9.66±0.05 eV, respectively, which are formed from cyclo(Gly-Gly) and cyclo(Ala-Ala) radical cations with HNCO elimination. Due to the stabilization of the radical cation of cyclo(Gly-Val) with isopropyl side group, the dominant fragment ion m/z 114 assigned as [C4H6N2O2]+• is produced by γ-H migration and i cleavage to lose propylene. The ionization energies (IEs) of three cyclic dipeptides decrease in the order cyclo(Gly-Gly) (9.33±0.05 eV)>cyclo(Ala-Ala) (9.21±0.05 eV)>cyclo(Gly-Val) (9.09±0.05 eV) from measurements of photoionization efficiency spectra. It implies that IEs of cyclic dipeptides are affected by substituent groups and symmetrical characterization of molecular structures. These observations of the chemical properties of cyclic dipeptides radical ion (M+•) may be important for understanding gas-phase molecular reactivity of 2,5-diketopiperazines and guiding diketopiperazine-based drug design.

show abstract

The synthesis and anticancer activity of selected diketopiperazines

Cited by 54 publications

References 24 publications

Crystal structure of hexahydro-7-hydroxy-3-(2-methylpropyl)pyrrolo [1,2-a]pyrazine-1,4-dione, C11H18N2O3

Crystal structure of hexahydro-7-hydroxy-3-(2-methylpropyl)pyrrolo [1,2-a]pyrazine-1,4-dione, C11H18N2O3

Hydrothermal reactions: From the synthesis of ligand to new lanthanide 3D-coordination polymers

Synchrotron vacuum ultraviolet (VUV) photo-induced fragmentation of cyclic dipeptides radical cations

Contact Info

Product

Resources

About