Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Bioorg Chem. 2024 Oct 22;153:107904. doi: 10.1016/j.bioorg.2024.107904. Online
 ahead of print.

Halogenated monopyridinium oximes are less effective in reactivation of 
phosphylated cholinesterases than bisquaternary oximes.

Kohoutova Z(1), Prchalova E(1), Andrys R(1), Knittelova K(1), Formanova M(1), 
Hofmanova T(1), Psotka M(2), Musilek K(2), Derat E(3), Malinak D(4).

Author information:
(1)University of Hradec Kralove, Faculty of Science, Department of Chemistry, 
Rokitanskeho 62, 500 03 Hradec Kralove, Czech Republic.
(2)University of Hradec Kralove, Faculty of Science, Department of Chemistry, 
Rokitanskeho 62, 500 03 Hradec Kralove, Czech Republic; University Hospital in 
Hradec Kralove, Biomedical Research Centre, Sokolska 581, 500 05 Hradec Kralove, 
Czech Republic.
(3)Parisian Institute of Molecular Chemistry, Sorbonne University, 4 place 
Jussieu, 75005 Paris, France. Electronic address: 
etienne.derat@sorbonne-universite.fr.
(4)University of Hradec Kralove, Faculty of Science, Department of Chemistry, 
Rokitanskeho 62, 500 03 Hradec Kralove, Czech Republic; University Hospital in 
Hradec Kralove, Biomedical Research Centre, Sokolska 581, 500 05 Hradec Kralove, 
Czech Republic. Electronic address: david.malinak@uhk.cz.

Mono-quaternary pyridinium oximes derived from K-oximes K027, K048 and K203 were 
designed, synthesized and evaluated for the reactivation of 
organophosphate-inhibited cholinesterases. The incorporation of the halogen 
atoms to the structure decreased the pKa value of the oxime group resulting in 
an increased formation of oximate necessary for reactivation. The stability and 
pKa values were found to be similar to analogous bis-quaternary compounds. Some 
mono-quaternary oximes resulted as relatively strong inhibitors of human 
acetylcholinesterase. Nevertheless, the reactivation ability of mono-quaternary 
oximes for organophosphate-inhibited cholinesterases was lower compared to their 
bis-quaternary analogues. These results were further confirmed by the 
determination of reactivation kinetics, when in some cases novel compounds 
showed improvement reactivation compared to the tested standards, but no 
improvement to bis-quaternary K-oximes. A computational study investigated 
reactivation process for K027, and its two analogues for VX-inhibited AChE. This 
study revealed slight differences between reactivation of mono-quaternary and 
bis-quaternary oximes. Abbreviations: 2-PAM, pralidoxime; AChE, 
acetylcholinesterase; ACN, acetonitrile; ATCI, acetylcholine iodide; BChE, 
butyrylcholinesterase; BTCI, butyrylcholine iodide; Bu3SnSnBu3, bis(tributyltin) 
Et2O, diethyl ether; ChEs, cholinesterases; CNS, central nervous system; DAD, 
diode array detector; DIBAL-H, diisobutylaluminium hydride; DMF, 
dimethylformamide; DMSO, dimethyl sulfoxide; DTNB, 5,5́-dithiobis-2-nitrobenzoic 
acid; Et3N, triethylamine; EtOAc, ethyl acetate; EWG, electron withdrawing 
group; HI-6, asoxime; hrAChE, human recombinant acetylcholinesterase; hrBChE, 
human recombinant butyrylcholinesterase; hrChEs, human recombinant 
cholinesterases; HPLC, high-performance liquid chromatography; HRMS, 
high-resolution mass spectrometry; KD, dissociation constant; kr, first-order 
reactivation rate constant; kr2, second-order reactivation rate constant; LüH-6, 
obidoxime; MeOH, methanol; MM, molecular mechanics; MMC-4, methoxime; m.p., 
melting point; NCIs, non-covalent interactions; NEDPA, 4-nitrophenyl ethyl 
dimethylphosphoramidate; NEMP, 4-nitrophenyl ethyl methylphosphonate; NIMP, 
isopropyl methylphosphonate; NMR, nuclear magnetic resonance spectroscopy; OPs, 
organophosphates; PBS, phosphate-buffered saline; Pd(dppf)Cl2.CH2Cl2, 
[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) in complex with 
dichloromethane; pKa, negative decimal logarithm of the dissociation constant; 
POX, paraoxon; PPh3, triphenylphosphine; QM, quantum mechanics; rt, room 
temperature; SN2, bimolecular nucleophilic substitution; SNAc, nucleophilic acyl 
substitution; THF, tetrahydrofuran; TMC-4, trimedoxime; TNB, 
5-thio-2-nitrobenzoic acid; UHPLC, ultra high-performance liquid chromatography; 
UV, ultraviolet; UV-VIS, ultraviolet-visible.

Copyright © 2024 Elsevier Inc. All rights reserved.

DOI: 10.1016/j.bioorg.2024.107904
PMID: 39467508

Conflict of interest statement: Declaration of competing interest The authors 
declare that they have no known competing financial interests or personal 
relationships that could have appeared to influence the work reported in this 
paper.


2. Environ Sci Pollut Res Int. 2024 Oct;31(49):59398-59415. doi: 
10.1007/s11356-024-34948-6. Epub 2024 Oct 1.

Enhanced adsorption-photodegradation of tetracycline using Ce-N-co-doped 
AC/TiO(2) photocatalyst: isotherms, kinetics, mechanism, and thermodynamic 
insight.

Rahman NAAA(1), Khasri A(2), Salleh NHM(1), Jamir MRM(3).

Author information:
(1)Faculty of Chemical Engineering & Technology, Universiti Malaysia Perlis 
(UniMAP), 02600, Arau, Perlis, Malaysia.
(2)Faculty of Chemical Engineering & Technology, Universiti Malaysia Perlis 
(UniMAP), 02600, Arau, Perlis, Malaysia. azduwin@unimap.edu.my.
(3)Faculty of Mechanical Engineering & Technology, Universiti Malaysia Perlis 
(UniMAP), 02600, Arau , Perlis, Malaysia.

Excessive use of tetracycline (TC) is alarming owing to its increased detection 
in water systems. In this study, a photocatalyst was developed to degrade TC 
using a Ce-N-co-doped AC/TiO2 photocatalyst, denoted as Ce/N-AC/TiO2, prepared 
using the sol-gel method assisted by microwave radiation, speeding up the 
synthesis process. Ce/N-AC/TiO2 achieved maximum TC degradation of 93.1% under 
UV light with optimum sorption system conditions of an initial concentration of 
10 mg L-1, pH 7, and 30 ℃, under 120 min. Scavenger experiments revealed that 
holes and superoxide radicals were the active species influencing the 
photodegradation process. The TC degradation was appropriately fitted with 
Langmuir isotherms and a pseudo-second-order (PSO) kinetic model. The change in 
enthalpy (ΔH) (2.43 kJ mol-1), entropy (ΔS) (0.024 kJ mol-1), and Gibbs free 
energy (ΔG) (- 4.941 to - 5.802 kJ mol-1) suggested that the adsorption process 
was spontaneous, favourable, and endothermic. Electrostatic interaction, 
hydrogen bonding, pore-filling, cationic-π, n-π, and π-π interaction were among 
the interactions involved between TC and Ce/N-AC/TiO2. Furthermore, Ce/N-AC/TiO2 
stability was confirmed through 80% removal efficiency even after the fifth 
reuse cycle. Notably, this work provides new insight into the production of 
efficient, reusable, and enhanced photocatalysts using a rapid and 
cost-effective microwave-assisted synthesis process for pollutant remediation.

© 2024. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, 
part of Springer Nature.

DOI: 10.1007/s11356-024-34948-6
PMID: 39354260 [Indexed for MEDLINE]


3. PLoS One. 2024 Sep 23;19(9):e0304609. doi: 10.1371/journal.pone.0304609. 
eCollection 2024.

TCP BBR-n interplay with modern AQM in Wireless-N/AC networks: Quest for the 
golden pair.

Ahsan M(1)(2), Muhammad SS(1).

Author information:
(1)Department of Electrical Engineering, National University of Computer & 
Emerging Sciences, Lahore, Punjab, Pakistan.
(2)Department of Software Engineering, University of Management and Technology, 
Lahore, Punjab, Pakistan.

Effective congestion control on the internet has been a problem since its 
inception. Transmission Control Protocol (TCP), being the most widely used 
transport layer protocol tries to mitigate it using a variety of congestion 
control algorithms. Cubic, Reno, and Bottleneck Bandwidth and Round-trip 
propagation time (BBR) are the most deployed congestion controls. BBR v2 is 
leading the congestion control race with its superior performance in terms of 
better throughput and lower latency. Furthermore, Active Queue Management (AQM) 
algorithms try to mitigate the congestion control at the network layer through 
active buffer control to avoid bufferbloat. The most efficient congestion 
control occurs when TCP and AQM work together. Indeed, it is the TCP-AQM 
algorithm "Golden pair" that can result in the most efficient performance. This 
paper proposes such a novel pair based on our previously tested and published 
BBR-n (BBR new) with the most effective of the modern AQMs, that completely gels 
together to provide lower latency in wireless networks based on Wireless N/AC. 
Real-time experiments were performed using Flent on our physical testbed with 
BBR-n and modern AQMs such as Fair Queuing (FQ), Constrained Delay (CoDel), 
Proportional Integral controller Enhanced (PIE), Common Applications Kept 
Enhanced (Cake) and Flow Queuing Controlled Delay (FQ_CoDel). Various tests done 
on our physical testbed helped us identify CAKE as the most optimum AQM that 
fits with our proposed BBR-n while providing optimum throughput and lower 
latency in 802.11N/AC-based wireless networks.

Copyright: © 2024 Ahsan, Muhammad. This is an open access article distributed 
under the terms of the Creative Commons Attribution License, which permits 
unrestricted use, distribution, and reproduction in any medium, provided the 
original author and source are credited.

DOI: 10.1371/journal.pone.0304609
PMCID: PMC11419378
PMID: 39312516 [Indexed for MEDLINE]

Conflict of interest statement: The authors have declared that no competing 
interests exist.


4. Physiol Mol Biol Plants. 2024 Jul;30(7):1085-1097. doi: 
10.1007/s12298-024-01481-2. Epub 2024 Jul 18.

Transcriptome and proteome analyses reveal high nitrate or ammonium applications 
alleviate photosynthetic decline of Phoebe bournei seedlings under elevated 
carbon dioxide by regulating glnA and rbcS.

Wang X(1)(2), Wei X(1), Wu G(1), Chen S(1).

Author information:
(1)College of Forestry, Guizhou University, Guiyang, China.
(2)College of Agriculture, Anshun University, Anshun, China.

The global CO2 concentration is predicted to reach 700 µmol·mol-1 by the end of 
this century. Phoebe bournei (Hemsl.) Yang is a precious timber species and is 
listed as a national secondary protection plant in China. P. bournei seedlings 
show obvious photosynthetic decline when grown long-term under an elevated CO2 
concentration (eCO2, EC). This decline can be alleviated by high nitrate or 
ammonium applications. However, the underlying mechanisms have not yet been 
elucidated. We performed transcriptomic and proteomic analyses of P. bournei of 
seedlings grown under an ambient CO2 concentration (AC) and applied with either 
a moderate level of nitrate (N), a high level of nitrate (hN), or a moderate 
level of ammonium (A) and compared them with those of seedlings grown under eCO2 
(i.e., AC_N vs EC_N, AC_hN vs EC_hN, AC_A vs EC_A) to identify differentially 
expressed genes (DEGs) and differentially expressed proteins (DEPs). We 
identified 4528 (AC_N vs EC_N), 1378 (AC_hN vs EC_hN), and 252 (AC_A vs EC_A) 
DEGs and 230, 514, and 234 DEPs, respectively, of which 59 specific genes and 21 
specific proteins were related to the regulation of photosynthesis by nitrogen 
under eCO2. A combined transcriptomic and proteomic analysis identified 7 
correlation-DEGs-DEPs genes. These correlation-DEGs-DEPs genes revealed crucial 
pathways involved in glyoxylate and dicarboxylate metabolism and nitrogen 
metabolism. The rbcS and glnA correlation-DEGs-DEPs genes were enriched in these 
two metabolisms. We propose that the rbcS and glnA correlation-DEGs-DEPs genes 
play an important role in photosynthetic decline and nitrogen regulation. High 
nitrate or ammonium applications alleviated the downregulation of glnA and rbcS 
and, hence, alleviated photosynthetic decline. The results of this study provide 
directions for the screening of germplasm resources and molecular breeding of P. 
bournei, which is tolerant to elevated CO2 concentrations.
SUPPLEMENTARY INFORMATION: The online version contains supplementary material 
available at 10.1007/s12298-024-01481-2.

© Prof. H.S. Srivastava Foundation for Science and Society 2024. Springer Nature 
or its licensor (e.g. a society or other partner) holds exclusive rights to this 
article under a publishing agreement with the author(s) or other 
rightsholder(s); author self-archiving of the accepted manuscript version of 
this article is solely governed by the terms of such publishing agreement and 
applicable law.

DOI: 10.1007/s12298-024-01481-2
PMCID: PMC11291807
PMID: 39100876

Conflict of interest statement: Conflict of interestThe authors declare that 
they have no competing interests.


5. Chemistry. 2024 Aug 27;30(48):e202402318. doi: 10.1002/chem.202402318. Epub
2024  Aug 2.

Glyco-DNA: Enzymatic Synthesis of Base-Modified and Hypermodified DNA Displaying 
up to Four Different Monosaccharide Units in the Major Groove.

Krömer M(1)(2), Poštová Slavětínská L(1), Hocek M(1)(2).

Author information:
(1)Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, 
Flemingovo nám. 2, 16000, Prague 6, Czech Republic.
(2)Department of Organic Chemistry, Faculty of Science, Charles University, 
Hlavova 8, 12843, Prague 2, Czech Republic.

A portfolio of six modified 2'-deoxyribonucleoside triphosphate (dNTP) 
derivatives derived from 5-substituted pyrimidine or 7-substituted 7-deazapurine 
bearing different carbohydrate units (d-glucose, d-galactose, d-mannose, 
l-fucose, sialic acid and N-Ac-d-galactosamine) tethered through 
propargyl-glycoside linker was designed and synthesized via the Sonogashira 
reactions of halogenated dNTPs with the corresponding propargyl-glycosides. The 
nucleotides were found to be good substrates for DNA polymerases in enzymatic 
primer extension and PCR synthesis of modified and hypermodified DNA displaying 
up to four different sugars. Proof of concept binding study of sugar-modified 
oligonucleotides with concanavalin A showed positive effect of avidity and sugar 
units count.

© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

DOI: 10.1002/chem.202402318
PMID: 38896019 [Indexed for MEDLINE]