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Article ; Online: Nucleophilic catalysis of p-substituted aniline derivatives in acylhydrazone formation and exchange.

Canal-Martín, Andrea / Navo, Claudio D / Sáez, Elena / Molero, Dolores / Jiménez-Osés, Gonzalo / Pérez-Fernández, Ruth

2021 Volume 19, Issue 33, Page(s) 7202–7210

Abstract: ... superior performance of electron-rich p-substituted aniline derivatives as catalysts for efficient ...

Abstract	Hydrazone bond formation is a versatile reaction employed in several research fields. It is one of the most popular reversible reactions in dynamic combinatorial chemistry. Under physiological conditions, hydrazone exchange benefits from the addition of a nucleophilic catalyst. We report a mechanistic study and superior performance of electron-rich p-substituted aniline derivatives as catalysts for efficient hydrazone formation and exchange in both protic and aprotic solvents. Rigorous kinetic analyses demonstrate that imine formation with 3-hydroxy-4-nitrobenzaldehyde and aniline derivatives proceeds with unprecedented third-order kinetics in which the aldehyde consistently shows a partial order of two. Computational investigations provide insights into the mechanisms of these transformations.
Language	English
Publishing date	2021-08-13
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/d1ob00871d
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Article ; Online: Epidemiological characteristics of the SARS-CoV-2 Theta variant (P.3) in the Central Visayas region, Philippines, 30 October 2020-16 February 2021.

Haw, Nel Jason L / Cañal, Eugenia Mercedes R / Zuasula, Juanito / Loreche, Mary Jean / Bernadas, Jaime

Western Pacific surveillance and response journal : WPSAR

2022 Volume 13, Issue 1, Page(s) 1–3

MeSH term(s)	COVID-19/epidemiology ; Humans ; Philippines/epidemiology ; SARS-CoV-2
Language	English
Publishing date	2022-02-09
Publishing country	Philippines
Document type	Journal Article
ZDB-ID	2592503-9
ISSN	2094-7313 ; 2094-7313
ISSN (online)	2094-7313
ISSN	2094-7313
DOI	10.5365/wpsar.2022.13.1.883
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Article ; Online: P(HPMA)-block-P(LA) copolymers in paclitaxel formulations: polylactide stereochemistry controls micellization, cellular uptake kinetics, intracellular localization and drug efficiency.

Barz, Matthias / Armiñán, Ana / Canal, Fabiana / Wolf, Florian / Koynov, Kaloian / Frey, Holger / Zentel, Rudolf / Vicent, María J

Journal of controlled release : official journal of the Controlled Release Society

2012 Volume 163, Issue 1, Page(s) 63–74

Abstract: ... hydroxypropyl)-methacrylamide)-block-poly(L-lactide) (P(HPMA)-block-P(LLA)) and poly(N-(2-hydroxypropyl ... methacrylamide)-block-poly(DL-lactide) block copolymers (P(HPMA)-block-P(DLLA)) were studied. To this end, P(HPMA ... block-P(lactide) block copolymers and their fluorescently labeled analogues were synthesized ...

Abstract	In order to explore the influence of polymer microstructure and stereochemistry in biological settings, the synthesis, micellization, cellular fate and the use in paclitaxel formulations of poly(N-(2-hydroxypropyl)-methacrylamide)-block-poly(L-lactide) (P(HPMA)-block-P(LLA)) and poly(N-(2-hydroxypropyl)-methacrylamide)-block-poly(DL-lactide) block copolymers (P(HPMA)-block-P(DLLA)) were studied. To this end, P(HPMA)-block-P(lactide) block copolymers and their fluorescently labeled analogues were synthesized. The polymers exhibited molecular weights M(n) around 20,000 g/mol with dispersities (D=M(w)/M(n)) below 1.3. In addition, the solution conformation of this new type of partially degradable amphiphilic block copolymers was studied with and without paclitaxel loading in PBS buffer (pH 7.2), employing fluorescence correlation spectroscopy (FCS). We observed polymeric micelles with a hydrodynamic diameter of 17.0 nm for a fluorescently labeled P(HPMA)-block-P(LLA) block copolymer (P2) and 20.4 nm for a P(HPMA)-block-P(DLLA) block copolymer (P3). For the corresponding loaded block copolymers aggregates with a diameter of 40.0 nm (P2) and 41.4 nm (P3) in formulations containing 17 wt.% paclitaxel were observed, respectively. While the block copolymer itself showed non-toxic behavior up to a concentration of 3 mg/mL in HeLa (human cervix adenocarcinoma) cells, the paclitaxel containing formulations showed IC 50 values in the range of 10-100 nM. The P(HPMA)-block-P(DLLA) polymer (P3) enters the cells more efficiently than stereo regular polymer (P2) via an energy-dependent uptake mechanism. Thus, differences in the IC(50) value are--most likely--attributed to significant changes in cellular uptake. Polymer tacticity and stereoregularity appear to represent a key feature determining cellular uptake and efficiency for the PLA block copolymer drug formulations. This work demonstrates the importance of the microstructure of polymers used in drug delivery systems (DDS).
MeSH term(s)	Antineoplastic Agents, Phytogenic/administration & dosage ; Antineoplastic Agents, Phytogenic/chemistry ; Biological Transport ; Cell Survival/drug effects ; HeLa Cells ; Humans ; Kinetics ; Methacrylates/administration & dosage ; Methacrylates/chemistry ; Micelles ; Molecular Conformation ; Paclitaxel/administration & dosage ; Paclitaxel/chemistry ; Polyesters/administration & dosage ; Polyesters/chemistry
Chemical Substances	Antineoplastic Agents, Phytogenic ; Methacrylates ; Micelles ; Polyesters ; poly(lactide) (459TN2L5F5) ; Paclitaxel (P88XT4IS4D) ; hydroxypropyl methacrylate (UKW89XAX2X)
Language	English
Publishing date	2012-10-10
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	632533-6
ISSN	1873-4995 ; 0168-3659
ISSN (online)	1873-4995
ISSN	0168-3659
DOI	10.1016/j.jconrel.2012.05.024
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Article: North African hybrid sparrows (Passer domesticus, P. hispaniolensis) back from oblivion - ecological segregation and asymmetric mitochondrial introgression between parental species.

Ait Belkacem, Abdelkrim / Gast, Oliver / Stuckas, Heiko / Canal, David / LoValvo, Mario / Giacalone, Gabriele / Päckert, Martin

Ecology and evolution

2016 Volume 6, Issue 15, Page(s) 5190–5206

Abstract: A stabilized hybrid form of the house sparrow (Passer domesticus) and the Spanish sparrow (P ... sparrow haplotypes. In contrast, populations of the Italian hybrid form, P. italiae, were genetically ...

Abstract	A stabilized hybrid form of the house sparrow (Passer domesticus) and the Spanish sparrow (P. hispaniolensis) is known as Passer italiae from the Italian Peninsula and a few Mediterranean islands. The growing attention for the Italian hybrid sparrow and increasing knowledge on its biology and genetic constitution greatly contrast the complete lack of knowledge of the long-known phenotypical hybrid sparrow populations from North Africa. Our study provides new data on the breeding biology and variation of mitochondrial DNA in three Algerian populations of house sparrows, Spanish sparrows, and phenotypical hybrids. In two field seasons, the two species occupied different breeding habitats: Spanish sparrows were only found in rural areas outside the cities and bred in open-cup nests built in large jujube bushes. In contrast, house sparrows bred only in the town centers and occupied nesting holes in walls of buildings. Phenotypical hybrids were always associated with house sparrow populations. House sparrows and phenotypical hybrids started breeding mid of March, and most pairs had three successive clutches, whereas Spanish sparrows started breeding almost one month later and had only two successive clutches. Mitochondrial introgression is strongly asymmetric because about 75% of the rural Spanish sparrow population carried house sparrow haplotypes. In contrast, populations of the Italian hybrid form, P. italiae, were genetically least diverse among all study populations and showed a near-fixation of house sparrow haplotypes that elsewhere were extremely rare or that were even unique for the Italian Peninsula. Such differences between mitochondrial gene pools of Italian and North African hybrid sparrow populations provide first evidence that different demographic histories have shaped the extant genetic diversity observed on both continents.
Language	English
Publishing date	2016-06-28
Publishing country	England
Document type	Journal Article
ISSN	2045-7758
ISSN	2045-7758
DOI	10.1002/ece3.2274
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Article ; Online: Effect of different dietary resources on longevity, carbohydrate metabolism, and ovarian dynamics in two fruit fly p

Narváez, Alexandra / Cancino, Jorge / Daza, Nelson Canal / Wyckhuys, Kris A.G.

Arthropod-Plant Interactions

2017

Keywords	tephritidae ; anastrepha ; parasitoids ; biological control ; parasitoides ; control biológico ; ecology
Language	English
Publishing date	2017-10-12T08:02:09Z
Publisher	Springer
Publishing country	fr
Document type	Article ; Online
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Article ; Online: Synthesis, Characterization and Preliminary Biological Evaluation of P(HPMA)-b-P(LLA) Copolymers: A New Type of Functional Biocompatible Block Copolymer.

Barz, Matthias / Wolf, Florian K / Canal, Fabiana / Koynov, Kaloian / Vicent, Maria J / Frey, Holger / Zentel, Rudolf

Macromolecular rapid communications

2010 Volume 31, Issue 17, Page(s) 1492–1500

Abstract: We describe a synthetic pathway to functional P(HPMA)-b-P(LLA) block copolymers. The synthesis ... transformed into biocompatible P(HPMA)-b-P(LLA) copolymers and their fluorescently labeled derivatives ...

Abstract	We describe a synthetic pathway to functional P(HPMA)-b-P(LLA) block copolymers. The synthesis relies on a combination of ring-opening polymerization of L-lactide, conversion into a chain transfer agent (CTA) for the RAFT polymerization of pentafluorophenyl methacrylate. A series of block copolymers was prepared that exhibited molecular weights $\overline M _{\rm n}$ ranging from 7 600 to 34 300 g · mol(-1) , with moderate PDI between 1.3 and 1.45. These reactive precursor polymers have been transformed into biocompatible P(HPMA)-b-P(LLA) copolymers and their fluorescently labeled derivatives by facile replacement of the pentafluorophenyl groups. The fluorescence label attached to this new type of a partially degradable amphiphilic block copolymer was used to study cellular uptake in human cervix adenocarcinoma (HeLa) cells as well as aggregation behavior by fluorescence correlation spectroscopy (FCS).
Language	English
Publishing date	2010-09-01
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1475027-2
ISSN	1521-3927 ; 1022-1336
ISSN (online)	1521-3927
ISSN	1022-1336
DOI	10.1002/marc.201000090
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Article ; Online: Dual-tasking modulates movement speed but not value-based choices during walking.

Grießbach, Eric / Raßbach, Philipp / Herbort, Oliver / Cañal-Bruland, Rouwen

Scientific reports

2024 Volume 14, Issue 1, Page(s) 6342

Abstract: Value-based decision-making often occurs in multitasking scenarios relying on both cognitive and motor processes. Yet, laboratory experiments often isolate these processes, thereby neglecting potential interactions. This isolated approach reveals a ... ...

Abstract	Value-based decision-making often occurs in multitasking scenarios relying on both cognitive and motor processes. Yet, laboratory experiments often isolate these processes, thereby neglecting potential interactions. This isolated approach reveals a dichotomy: the cognitive process by which reward influences decision-making is capacity-limited, whereas the influence of motor cost is free of such constraints. If true, dual-tasking should predominantly impair reward processing but not affect the impact of motor costs. To test this hypothesis, we designed a decision-making task in which participants made choices to walk toward targets for rewards while navigating past an obstacle. The motor cost to reach these rewards varied in real-time. Participants either solely performed the decision-making task, or additionally performed a secondary pitch-recall task. Results revealed that while both reward and motor costs influenced decision-making, the secondary task did not affect these factors. Instead, dual-tasking slowed down participants' walking, thereby reducing the overall reward rate. Hence, contrary to the prediction that the added cognitive demand would affect the weighing of reward or motor cost differentially, these processes seem to be maintained at the expense of slowing down the motor system. This slowdown may be indicative of interference at the locomotor level, thereby underpinning motor-cognitive interactions during decision-making.
MeSH term(s)	Humans ; Walking ; Movement ; Reward ; Mental Recall ; Cognition
Language	English
Publishing date	2024-03-15
Publishing country	England
Document type	Journal Article
ZDB-ID	2615211-3
ISSN	2045-2322 ; 2045-2322
ISSN (online)	2045-2322
ISSN	2045-2322
DOI	10.1038/s41598-024-56937-y
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Article: P(HPMA)-block-P(LA) copolymers in paclitaxel formulations: Polylactide stereochemistry controls micellization, cellular uptake kinetics, intracellular localization and drug efficiency

Barz, Matthias / Armiñán, Ana / Canal, Fabiana / Wolf, Florian / Koynov, Kaloian / Frey, Holger / Zentel, Rudolf / Vicent, María J

Journal of controlled release. 2012 Oct. 10, v. 163, no. 1

2012

Abstract: ... hydroxypropyl)-methacrylamide)-block-poly(l-lactide) (P(HPMA)-block-P(LLA)) and poly(N-(2-hydroxypropyl ... methacrylamide)-block-poly(dl-lactide) block copolymers (P(HPMA)-block-P(DLLA)) were studied. To this end, P(HPMA ... block-P(lactide) block copolymers and their fluorescently labeled analogues were synthesized ...

Abstract	In order to explore the influence of polymer microstructure and stereochemistry in biological settings, the synthesis, micellization, cellular fate and the use in paclitaxel formulations of poly(N-(2-hydroxypropyl)-methacrylamide)-block-poly(l-lactide) (P(HPMA)-block-P(LLA)) and poly(N-(2-hydroxypropyl)-methacrylamide)-block-poly(dl-lactide) block copolymers (P(HPMA)-block-P(DLLA)) were studied. To this end, P(HPMA)-block-P(lactide) block copolymers and their fluorescently labeled analogues were synthesized. The polymers exhibited molecular weights Mₙ around 20,000g/mol with dispersities (D=Mw/Mₙ) below 1.3. In addition, the solution conformation of this new type of partially degradable amphiphilic block copolymers was studied with and without paclitaxel loading in PBS buffer (pH 7.2), employing fluorescence correlation spectroscopy (FCS). We observed polymeric micelles with a hydrodynamic diameter of 17.0nm for a fluorescently labeled P(HPMA)-block-P(LLA) block copolymer (P2) and 20.4nm for a P(HPMA)-block-P(DLLA) block copolymer (P3). For the corresponding loaded block copolymers aggregates with a diameter of 40.0nm (P2) and 41.4nm (P3) in formulations containing 17wt.% paclitaxel were observed, respectively. While the block copolymer itself showed non-toxic behavior up to a concentration of 3mg/mL in HeLa (human cervix adenocarcinoma) cells, the paclitaxel containing formulations showed IC 50 values in the range of 10–100nM. The P(HPMA)-block-P(DLLA) polymer (P3) enters the cells more efficiently than stereo regular polymer (P2) via an energy-dependent uptake mechanism. Thus, differences in the IC₅₀ value are – most likely – attributed to significant changes in cellular uptake. Polymer tacticity and stereoregularity appear to represent a key feature determining cellular uptake and efficiency for the PLA block copolymer drug formulations. This work demonstrates the importance of the microstructure of polymers used in drug delivery systems (DDS).
Keywords	adenocarcinoma ; cervix ; composite polymers ; drug delivery systems ; drug formulations ; drugs ; fluorescence ; humans ; hydrodynamics ; inhibitory concentration 50 ; micelles ; microstructure ; molecular weight ; pH ; paclitaxel ; polylactic acid ; spectroscopy ; stereochemistry
Language	English
Dates of publication	2012-1010
Size	p. 63-74.
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	632533-6
ISSN	1873-4995 ; 0168-3659
ISSN (online)	1873-4995
ISSN	0168-3659
DOI	10.1016/j.jconrel.2012.05.024
Database	NAL-Catalogue (AGRICOLA)

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Article: Relationship between N, P, and K and the quality and stem structural characteristics of Caesalpinia echinata Lam. plants

Cuzzuol, Geraldo Rogério Faustini / Milanez, Camilla Rozindo Dias / Gomes, José Manoel Lúcio / Labate, Carlos Alberto / Canal, Emerson Campos

Trees - structure and function. 2013 Oct., v. 27, no. 5

2013

Abstract: This study was carried out to evaluate the effect of N, P, and K on the growth of Caesalpinia ... where they received N, P, and K in isolated form, and NPK combined in 10:10:10 and 04:14:08 ratios. The applications ... were higher in P and K when compared to N and the NPK forms. Nevertheless, the levels of xylose and ...

Abstract	This study was carried out to evaluate the effect of N, P, and K on the growth of Caesalpinia echinata plants and on the anatomical and chemical characteristics of their stems. Eight-month-old plants were grown in polyethylene pots of 8� L containing soil. The pots were arranged in randomized blocks where they received N, P, and K in isolated form, and NPK combined in 10:10:10 and 04:14:08 ratios. The applications were repeated at intervals of 90� days for 450� days, between January 2008 and April 2009. The nitrogen fertilization (N) and in the form NPK 04:14:08 provided greater stem growth and leaf area, but with lower values of Dickson quality index, which suggests lower survival potential under field conditions. Fertilizations do not influence the insoluble lignin concentration and the components of cellulose and hemicelluloses of the secondary xylem of the stem. In the stem bark, however, the levels of xylose, glucose, and insoluble lignin were higher in P and K when compared to N and the NPK forms. Nevertheless, the levels of xylose and insoluble lignin in all the treatments were lower than those in the control group. Concerning anatomical characteristics, there was higher diameter of the vessel element and reduced length of its cells for the NPK combination. All the fertilizing formulas reduced fiber wall thickness of the secondary xylem compared to control. The results suggest phosphate fertilization as the most recommended for growing C. echinata plants with increased chances of survival under field conditions.
Keywords	Caesalpinia ; bark ; cellulose ; glucose ; leaf area ; lignin ; nitrogen fertilizers ; secondary xylem ; stem elongation ; stems
Language	English
Dates of publication	2013-10
Size	p. 1477-1484.
Publishing place	Springer-Verlag
Document type	Article
ZDB-ID	90595-1
ISSN	1432-2285 ; 0931-1890
ISSN (online)	1432-2285
ISSN	0931-1890
DOI	10.1007/s00468-013-0894-9
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Embodied decision biases: individually stable across different tasks?

Grießbach, Eric / Raßbach, Philipp / Herbort, Oliver / Cañal-Bruland, Rouwen

Experimental brain research

2023 Volume 241, Issue 4, Page(s) 1053–1064

Abstract: In everyday life, action and decision-making often run in parallel. Action-based models argue that action and decision-making strongly interact and, more specifically, that action can bias decision-making. This embodied decision bias is thought to ... ...

Abstract	In everyday life, action and decision-making often run in parallel. Action-based models argue that action and decision-making strongly interact and, more specifically, that action can bias decision-making. This embodied decision bias is thought to originate from changes in motor costs and/or cognitive crosstalk. Recent research confirmed embodied decision biases for different tasks including walking and manual movements. Yet, whether such biases generalize within individuals across different tasks remains to be determined. To test this, we used two different decision-making tasks that have independently been shown to reliably produce embodied decision biases. In a within-participant design, participants performed two tasks in a counterbalanced fashion: (i) a walking paradigm for which it is known that motor costs systematically influence reward decisions, and (ii) a manual movement task in which motor costs and cognitive crosstalk have been shown to impact reward decisions. In both tasks, we successfully replicated the predicted embodied decision biases. However, there was no evidence that the strength of the biases correlated between tasks. Hence, our findings do not confirm that embodied decision biases transfer between tasks. Future research is needed to examine whether this lack of transfer may be due to different causes underlying the impact of motor costs on decisions and the impact of cognitive crosstalk or task-specific differences.
MeSH term(s)	Humans ; Decision Making ; Movement ; Bias ; Walking ; Reward
Language	English
Publishing date	2023-03-13
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1201-4
ISSN	1432-1106 ; 0014-4819
ISSN (online)	1432-1106
ISSN	0014-4819
DOI	10.1007/s00221-023-06591-z
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