Introductory Chapter: Sea Urchin - Knowledge and Perspectives

Agnello, Maria

doi:10.5772/intechopen.70415

Cited by 3 publications

(4 citation statements)

References 46 publications

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“…Light brown solid; 140 mg (72%); mp 171−173 °C (lit. 53 (21), 356 [M] + (100), 341 (28), 162 (13), 155 (12), 140 (10), 133 (10), 127 (10), 119 (49), 105 (14), 91 (21), 77 (15) (21), 296 [M] + (100), 281 (22), 263 (12), 253 (12), 235 (16), 118 (10) (6), 341 (40), 327 (1), 313 (7), 118 (11), 91 (16) (18), 296 [M] + (100), 281 (7), 263 (8), 253 (6), 235 (12), 221 (11), 127 (12), 118 (12), 91 (12), 77 (30) (5), 171 (13), 170 (11), 169 (33), 140 (12), 127 (11) (19), 385 [M] + (100), 371 (7), 370 (36), 140 (10), 139 (12), 77 (6) (25 mL), the resulting mixture was stirred for 24 h at room temperature, concentrated in vacuo, and treated with CH 2 Cl 2 (10 mL), followed by distilled water (2 × 15 mL). The organic phase was dried over MgSO 4 , concentr...…”

Section: -( 4 -M E T H O X Y --N I T R Omentioning

confidence: 99%

“…4 Hz, H-3″,5″), 6.81 (1H, dd, J = 8.2 Hz, J = 1.8 Hz, H-6′), 4.93 (2H, s, OCH 2 ), 3.77 (3H, s, OCH 3 ), 3.76 (3H, s, OCH 3 ); 13 5-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrazole hydrochloride (1l) (Scheme 3, Path B). White solid; 23 mg (16%); mp 108−110 °C; 1 H NMR (DMSO-d 6 ) δ 7.87 (1H, s, H-3), 6.97 (1H, d, J = 2.0 Hz, H-8″), 6.94 (0.5H, d, J = 2.0 Hz, H-7″), 6.92 (0.5H, d, J = 2.0 Hz, H-7″), 6.89 (0.5H, s, H-5″), 6.87 (0.5H, s, H-5″), 6.57 (2H, s, H-2′,6′), 4.24 (4H, s, H-2″,3″), 3.66 (3H, s, OCH 3 -4′), 3.56 (6H, s, OCH 3 -3′,5′); EIMS m/z 369 [M + 1] + (10), 368 (65), 353 (52), 239 (20), 211 (17), 195 (23), 183 (23), 168 (24), 163 (31), 155 (41), 140 (31), 139 (33), 128 (21), 127 (27), 126 (23), 107 (20), 89 (21), 79 (34), 77 (48) (24), 354 [M] + (100), 339 (8), 309 (6), 281 (11), 161 (15), 155 (12), 140 (7), 77 (6) (23), 340 [M] + (100), 326 (10), 325 (46), 265 (11), 250 (16), 211 (11), 168 (11), 155 (15), 154 (21), 140 (11), 139 (13), 119 (10), 77 (10) (22), 373 (22)…”

Section: -( 4 -M E T H O X Y --N I T R Omentioning

confidence: 99%

“…While searching for novel microtubule dynamics modulating compounds, we selected a sea urchin embryo model for the phenotypic assay. This organism is well characterized and widely used in experimental biology to study various aspects of embryology, developmental and molecular biology, genetics, and ecology. − There are multiple advantages to a sea urchin embryo over alternative biological models. These include (a) simple access to a large number of gametes, (b) facile artificial fertilization and rearing, (c) quick and synchronous cell division during early embryogenesis, (d) well studied differentiation and morphogenesis, and (e) direct relevance to mammalian and human signaling networks.…”

Section: Introductionmentioning

confidence: 99%

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Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents

et al. 2018

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A series of both novel and reported combretastatin analogues, including diarylpyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles, were synthesized via improved protocols to evaluate their antimitotic antitubulin activity using in vivo sea urchin embryo assay and a panel of human cancer cells. A systematic comparative structure–activity relationship studies of these compounds were conducted. Pyrazoles 1i and 1p, isoxazole 3a, and triazole 7b were found to be the most potent antimitotics across all tested compounds causing cleavage alteration of the sea urchin embryo at 1, 0.25, 1, and 0.5 nM, respectively. These agents exhibited comparable cytotoxicity against human cancer cells. Structure–activity relationship studies revealed that compounds substituted with 3,4,5-trimethoxyphenyl ring A and 4-methoxyphenyl ring B displayed the highest activity. 3-Hydroxy group in the ring B was essential for the antiproliferative activity in the diarylisoxazole series, whereas it was not required for potency of diarylpyrazoles. Isoxazoles 3 with 3,4,5-trimethoxy-substituted ring A and 3-hydroxy-4-methoxy-substituted ring B were more active than the respective pyrazoles 1. Of the azoles substituted with the same set of other aryl pharmacophores, diarylpyrazoles 1, 4,5-diarylisoxazoles 3, and 4,5-diaryl-1,2,3-triazoles 7 displayed similar strongest antimitotic antitubulin effect followed by 3,4-diarylisoxazoles 5, 1,5-diaryl-1,2,3-triazoles 8, and pyrroles 10 that showed the lowest activity. Introduction of the amino group into the heterocyclic core decreased the antimitotic antitubulin effect of pyrazoles, triazoles, and to a lesser degree of 4,5-diarylisoxazoles, whereas potency of the respective 3,4-diarylisoxazoles was increased.

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Section: -( 4 -M E T H O X Y --N I T R Omentioning

confidence: 99%

Section: -( 4 -M E T H O X Y --N I T R Omentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents

et al. 2018

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“…In vivo bioassays allow for the more accurate determination of effects when a general toxicological answer is evaluated at organism level (e.g., zebrafish [ 29 ] at early life stages, mudsnails [ 31 ], mussels [ 32 ] or sea urchins [ 30 ]) and, when local organisms are used, the contamination of a specific area can be more precisely determined. In this sense, the sea urchin ( Paracentrotus lividus ) embryo test (SET) has arisen as a key in vivo assay for coastal marine/estuarine ecosystems [ 33 ]. Their use has been included in the European Union Reference Laboratory for Alternatives to Animal Testing ( sea urchin embryo test , SET), and it has been standardized by several national environmental agencies [ 34 , 35 , 36 ].…”

Section: Introductionmentioning

confidence: 99%

Suspect Screening of Chemicals in Hospital Wastewaters Using Effect-Directed Analysis Approach as Prioritization Strategy

et al. 2023

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The increasing number of contaminants in the environment has pushed water monitoring programs to find out the most hazardous known and unknown chemicals in the environment. Sample treatment-simplification methods and non-target screening approaches can help researchers to not overlook potential chemicals present in complex aqueous samples. In this work, an effect-directed analysis (EDA) protocol using the sea urchin embryo test (SET) as a toxicological in vivo bioassay was used as simplified strategy to identify potential unknown chemicals present in a very complex aqueous matrix such as hospital effluent. The SET bioassay was used for the first time here to evaluate potential toxic fractions in hospital effluent, which were obtained after a two-step fractionation using C18 and aminopropyl chromatographic semi-preparative columns. The unknown compounds present in the toxic fractions were identified by means of liquid chromatography coupled to a Q Exactive Orbitrap high-resolution mass spectrometer (LC-HRMS) and using a suspect analysis approach. The results were complemented by gas chromatography-mass spectrometry analysis (GC-MS) in order to identify the widest range of chemical compounds present in the sample and the toxic fractions. Using EDA as sample treatment simplification method, the number of unknown chemicals (>446 features) detected in the raw sample was narrowed down to 94 potential toxic candidates identified in the significantly toxic fractions. Among them, the presence of 25 compounds was confirmed with available chemical standards including 14 pharmaceuticals, a personal care product, six pesticides and four industrial products. The observations found in this work emphasize the difficulties in identifying potential toxicity drivers in complex water samples, as in the case of hospital wastewater.

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Triphenylphosphonium conjugates of 1,2,3-triazolyl nucleoside analogues. Synthesis and cytotoxicity evaluation

et al. 2020

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Introductory Chapter: Sea Urchin - Knowledge and Perspectives

Cited by 3 publications

References 46 publications

Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents

Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents

Suspect Screening of Chemicals in Hospital Wastewaters Using Effect-Directed Analysis Approach as Prioritization Strategy

Triphenylphosphonium conjugates of 1,2,3-triazolyl nucleoside analogues. Synthesis and cytotoxicity evaluation

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