Mimics of pramanicin derived from pyroglutamic acid and their antibacterial activity

Tan, Song Wei Benjamin; Chai, Christina L. L.; Moloney, Mark G.

doi:10.1039/c6ob02828d

Cited by 17 publications

(14 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Also L-PGA possess numerous neurologist interest since it competence to treat Alzheimer disease. Regarding to their antibacterial activity [ 59 ], antioxidant activity [ 60 ], anti-inflammatory activity on RAW 264.7 macrophages [ 61 ], the L-PGA and its derivatives were in the front line of interest of many chemist and biologist. In the present work, we have been using this compound to evaluate its capacity in the inhibition of COVID-19 by using four types of coronaviruses (6LU7, 6M03, 6W63 and 7BTF).…”

Section: Resultsmentioning

confidence: 99%

Searching potential antiviral candidates for the treatment of the 2019 novel coronavirus based on DFT calculations and molecular docking

Sagaama

Brandán

Issa

et al. 2020

Heliyon

View full text Add to dashboard Cite

In the present work, the succinic acid (SA), L-pyroglutamic acid (L-PGA), N-phenyl-thioacetamide (N-NPTA), 2-amino-5-chloropyridine hydrogen succinate (ACPS), epigallocatechine Gallate (EGCG) or KDH and, selenomethionine (SeM) compounds have been proposed as potential antiviral candidates to treatment of COVID-19 based on B3LYP/6-311++G∗∗ calculations and molecular docking. Solvation energies, stabilization energies, topological properties have been evaluated as function of acceptors and donors groups present in their structures. ACPS presents the higher reactivity in solution possibly because has the higher nucleophilicity and elecrophilicity indexes while KDH evidence the higher solvation energy probably due to the higher quantity of donors and acceptors groups. NBO studies show that KDH is the most stable in solution. Mapped MEP surfaces have evidenced stronger nucleophilic and electrophilic sites in ACPS, in agreement with the three C=O and two N–H and O–H groups present in this species while KDH has only a C=O group but a total of 19 acceptors and donors groups. From the above studies for six species we can propose that the better potential antiviral candidate to treatment of COVID-19 is ACPS and then, KDH. For a better prediction of the antiviral and anti-inflammatory properties of the proposed compounds, molecular docking calculations were performed by using four structures of COVID-19. Docking results were discussed basing on binding affinities and the interaction types among ligands and different amino acid residues, indicating the powerful ability of KDH and then ACPS ligands on front of the novel coronavirus disease especially for the first and the fourth species (6LU7, 7BTF).

show abstract

Section: Resultsmentioning

confidence: 99%

Searching potential antiviral candidates for the treatment of the 2019 novel coronavirus based on DFT calculations and molecular docking

Sagaama

Brandán

Issa

et al. 2020

Heliyon

View full text Add to dashboard Cite

show abstract

“…( Schwartz et al, 1994 ), the latter contained an epoxide group at C-10/C-11 instead of a double bond. The absolute configuration of pramanicin A ( 1 ) was deduced by comparison to pramanicin through biogenetic considerations ( Duspara et al, 1998 ; Harrison et al, 1998 , 2000 ; Chen and Harrison, 2004 ) and by total synthesis ( Cow et al, 1997 ; Barrett et al, 1999a , b ; Tan et al, 2014 , 2015 , 2017 ), which confirmed that the compound has (3 S ,4 S ,5 S ) configuration. The large absolute value of the specific optical rotation (SOR) of 1 allowed testing the TDDFT-SOR method ( Polavarapu, 2002 ; Mándi and Kurtán, 2019 ) and the ωB97X functional ( Chai and Head-Gordon, 2008 ; Bremond et al, 2016 ), which was also applied for the TDDFT-ECD calculations of 2 .…”

Section: Resultsmentioning

confidence: 68%

Induction of New Lactam Derivatives From the Endophytic Fungus Aplosporella javeedii Through an OSMAC Approach

et al. 2020

View full text Add to dashboard Cite

Fermentation of the endophytic fungus Aplosporella javeedii on solid rice medium in presence of either 3.5% NaNO 3 or 3.5% monosodium glutamate caused a significant change of the fungal metabolite pattern compared to fungal controls grown only on rice. Chemical investigation of the former fungal extracts yielded 11 new lactam derivatives, aplosporellins A–K ( 2 – 12 ), in addition to the known compound, pramanicin A ( 1 ). All of these compounds were not detected when the fungus was grown on rice medium without these activators thereby indicating the power of this OSMAC approach. The structures of the new compounds were elucidated by one- and two- dimensional NMR spectroscopy, DFT-NMR calculations and by mass spectrometry as well as by comparison with the literature whereas the absolute configuration of the lactam core was determined by TDDFT-ECD and OR calculations. Pramanicin A ( 1 ) showed strong cytotoxicity against human lymphoma (Ramos) and leukemia (Jurkat J16) cells with IC 50 values of 4.7 and 4.4 μM, respectively. Mechanistic studies indicated that 1 activates caspase-3 and induces apoptotic cell death.

show abstract

“…56 Dihydroxylation of enelactam 29 was also easily achievable, giving exclusively the exo product 33, but further elaboration unfortunately required protection to 34, adding additional steps to the sequence, although the desired product 35 could nonetheless be obtained again by Grignard reaction. 57 The Grignard displacement on these densely functionalised Weinreb amides was uneventful and highly chemoselective, notwithstanding the high level of chemical functionality in the bicyclic ring system, the only complication arising from the need for additional equivalents of Grignard reagents to account for the additional acidic hydrogens of the substrates. These systems could be deprotected under acidic conditions, providing access to hydroxylated products 28, 32 and 36 (Scheme 2).…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Functionalised Nitrogen Heterocycles and the Search for New Antibacterials and Bioactives

Khan

Wang²,

Moloney³

2020

Synthesis

Self Cite

View full text Add to dashboard Cite

The importance of, and synthetic routes to, pyrrolidines and piperidines, along with their relevance to natural product synthesis and antibacterial drug discovery, are surveyed in the context of an extended programme of investigation from our own laboratories.1 Introduction2 Pyroglutamates2.1 Synthesised by Modification of an Existing Ring2.2 Synthesised by Construction of a New Ring3 Tetramates4 Metal Chelation5 Biological Activity6 Conclusion

show abstract

Mimics of pramanicin derived from pyroglutamic acid and their antibacterial activity

Cited by 17 publications

References 55 publications

Searching potential antiviral candidates for the treatment of the 2019 novel coronavirus based on DFT calculations and molecular docking

Searching potential antiviral candidates for the treatment of the 2019 novel coronavirus based on DFT calculations and molecular docking

Induction of New Lactam Derivatives From the Endophytic Fungus Aplosporella javeedii Through an OSMAC Approach

Functionalised Nitrogen Heterocycles and the Search for New Antibacterials and Bioactives

Contact Info

Product

Resources

About