Category: 1466420-02-9

Longo, Beatrice published the artcileDesign, synthesis, conjugation and reactivity of novel trans,trans-1,5-cyclooctadiene-derived bioorthogonal linkers, Application In Synthesis of 1466420-02-9, the publication is Bioconjugate Chemistry (2020), 31(9), 2201-2210, database is CAplus and MEDLINE.

The tetrazine/trans cyclooctene (TCO) inverse-electron-demand Diels-Alder (IEDDA) reaction is the fastest bioorthogonal ”click” ligation process reported to date. In this context, TCO reagents have found widespread applications, however their availability and structural diversity is still somewhat limited, due to challenges connected with their synthesis and structural modification. To address this issue, a novel strategy for the conjugation of TCO derivatives to a biomol. was developed, which allows for the creation of greater structural diversity from a single precursor mol., i.e. trans,trans-1,5-cyclooctadiene [(E,E)-COD], whose preparation requires standard laboratory equipment and readily available reagents. This two-step strategy relies on the use of new bifunctional TCO-linkers (3aSR,9aSR,E)-I (R = 2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl, 2-[2-(2-(2-[(4-nitrophenoxycarbonyl)oxy]ethoxy)ethoxy)ethoxy]ethyl, (4-([(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl)phenyl)methyl, etc.) for IEDDA reactions, which can be synthesized via 1,3-dipolar cycloaddition of (E,E)-COD with different azido-spacers RN₃ carrying an electrophilic function (NHS-ester, N-succinimidyl carbonate, p-nitrophenyl-carbonate, maleimide) in the ¦Ø-position. Following bioconjugation of these electrophilic linkers to the nucleophilic residue (cysteine or lysine) of a protein (step 1), the resulting TCO-decorated constructs can be subjected to a IEDDA reaction with tetrazines functionalized with fluorescent or near IR (NIR) tags (step 2). This strategy to label bovine serum albumin with the TCO-linker (3aSR,9aSR,E)-I (II, R = 14-[(2,5-dioxopyrrolidin-1-yl)oxy]-14-oxo-3,6,9,12-tetraoxatetradecan-1-yl) and to subsequently react it in a cell lysate with the fluorescein-isothiocyanate (FITC)-derived tetrazine II was successfully used. The same strategy was then used to label the bacterial wall of gram-pos. S. aureus showing the potential of these linkers for live-cell imaging. Finally, the impact of structural differences of the linkers upon the stability of the bioorthogonal constructs was determined The compounds for stability studies were prepared by conjugation of TCO-linkers (3aSR,9aSR,E)-I (R = (4-([(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl)phenyl)methyl, 2-[2-(2-(2-[(4-nitrophenoxycarbonyl)oxy]ethoxy)ethoxy)ethoxy]ethyl, II) to mAbs, such as Rituximab and Obinutuzumab, and subsequent labeling with a reactive Cy3-functionalized tetrazine.

Bioconjugate Chemistry published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, Application In Synthesis of 1466420-02-9.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Rashidian, Mohammad published the artcileEnzyme-Mediated Modification of Single-Domain Antibodies for Imaging Modalities with Different Characteristics, Application In Synthesis of 1466420-02-9, the publication is Angewandte Chemie, International Edition (2016), 55(2), 528-533, database is CAplus and MEDLINE.

Antibodies are currently the fastest-growing class of therapeutics. Although naked antibodies proved valuable as pharmaceutical agents, they have some limitations, such as low tissue penetration and a long circulatory half-life. They have been conjugated to toxic payloads, PEGs, or radioisotopes to increase and optimize their therapeutic efficacy. Although nonspecific conjugation is suitable for most in vitro applications, it has become evident that site specifically modified antibodies may have advantages for in vivo applications. Herein the authors describe a novel approach in which the antibody fragment is tagged with two handles: one for the introduction of a fluorophore or ¹⁸F isotope, and the second for further modification of the fragment with a PEG moiety or a second antibody fragment to tune its circulatory half-life or its avidity. Such constructs, which recognize Class II MHC products and CD11b, showed high avidity and specificity. They were used to image cancers and could detect small tumors.

Angewandte Chemie, International Edition published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, Application In Synthesis of 1466420-02-9.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kim, Dahham published the artcileTwo-Photon and Multicolor Fluorogenic Bioorthogonal Probes Based on Tetrazine-Conjugated Naphthalene Fluorophores, HPLC of Formula: 1466420-02-9, the publication is Bioconjugate Chemistry (2020), 31(5), 1545-1550, database is CAplus and MEDLINE.

Herein, we report the use of two-photon fluorogenic probes using tetrazine-based bioorthogonal reactions with multicolor emissions that cover nearly all of the visible region. New fluorogenic probes were designed based on donor-acceptor-type naphthalene structures conjugated with a fluorescence-quenching tetrazine moiety for turn-on properties in one- and two-photon fluorescence. Our fluorescent probes showed a moderate to good turn-on ratio after bioorthogonal inverse electron demand Diels-Alder cycloaddition with trans-cyclooctenol in one- and two-photon fluorescence. We successfully applied our probes to mitochondria- and lysosome-selective bioorthogonal imaging in live cells with one-/two-photon and one-photon microscopy, resp.

Bioconjugate Chemistry published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, HPLC of Formula: 1466420-02-9.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Lee, Youngjun published the artcileMonochromophoric Design Strategy for Tetrazine-Based Colorful Bioorthogonal Probes with a Single Fluorescent Core Skeleton, Computed Properties of 1466420-02-9, the publication is Journal of the American Chemical Society (2018), 140(3), 974-983, database is CAplus and MEDLINE.

Fluorogenic bioorthogonal probes are ideal for fluorescent imaging in live cell conditions. By taking advantage of the dual functionality of tetrazine (Tz), as a bioorthogonal reaction unit as well as a fluorescence quencher, a fluorophore-Tz conjugate (FL_Tz) has been utilized for fluorescent live cell imaging via inverse electron-demand Diels-Alder (iEDDA) type bioorthogonal reactions. However, most FL_Tz strategies rely on a donor-acceptor-type energy transfer mechanism, which limits red-shifting of probes’ emission wavelength without deterioration of the fluorescent turn-on/off ratio. To address this constraint, herein the authors present a monochromophoric design strategy for making a series of FL_Tzs spanning a broad range of emission colors. For the systematic comparison of design strategies with minimized structural differences, the authors selected indolizine-based emission-tunable Seoul-Fluor (SF) as a model fluorophore system. As a result, by inducing strong electronic coupling between Tz and ¦Ð-conjugation systems of an indolizine core, the authors efficiently quench the fluorescence of SF-tetrazine conjugates (SF_Tzs) and achieved more than 1000-fold enhancement in fluorescence after iEDDA reaction with trans-cyclooctene (TCO). Importantly, the authors were able to develop a series of colorful SF_Tzs with a similar turn-on/off ratio regardless of their emission wavelength. The applicability as bioorthogonal probes was demonstrated with fluorescence bioimaging of innate microtubule and mitochondria using docetaxel-TCO and triphenylphosphonium-TCO in live cells without washing steps. The authors believe this study could provide new insight for the reliable and generally applicable mol. design strategy to develop bioorthogonal fluorogenic probes having an excellent turn-on ratio, regardless of their emission wavelength.

Journal of the American Chemical Society published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, Computed Properties of 1466420-02-9.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Allott, Louis published the artcileDetecting hypoxia in vitro using ¹⁸F-pretargeted IEDDA “click” chemistry in live cells, Related Products of catalysis-chemistry, the publication is RSC Advances (2021), 11(33), 20335-20341, database is CAplus and MEDLINE.

We have exemplified a pretargeted approach to interrogate hypoxia in live cells using radioactive bioorthogonal inverse electron demand Diels-Alder (IEDDA) “click” chem. Our novel ¹⁸F-tetrazine probe ([¹⁸F]FB-Tz) and 2-nitroimidazole-based TCO targeting mol. (8) showed statistically significant (P < 0.0001) uptake in hypoxic cells (ca. 90%ID per mg) vs. normoxic cells (<10%ID per mg) in a 60 min incubation of [¹⁸F]FB-Tz. This is the first time that an intracellularly targeted small-mol. for IEDDA “click” has been used in conjunction with a radioactive reporter mol. in live cells and may be a useful tool with far-reaching applicability for a variety of applications.

RSC Advances published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Wieczorek, Achim published the artcileRigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels-Alder reaction, Safety of (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, the publication is Organic & Biomolecular Chemistry (2014), 12(24), 4177-4185, database is CAplus and MEDLINE.

1,2,4,5-Tetrazine fluorophore derivatives with structurally rigid mol. designs were synthesized using Sonogashira and Stille cross-coupling as well as copper-catalyzed azide-alkyne cycloaddition The synthesized bichromophoric systems exhibit low fluorescence quantum yields due to quenching by the tetrazine. The extent of fluorescence quenching observed for those systems depends on the distance between the fluorophore and the tetrazine. The decreased fluorescence is “turned on” by conversion of the tetrazine in the inverse electron demand Diels-Alder cycloaddition Time resolved spectroscopy indicated resonance energy transfer between BODIPY and the tetrazine as the underlying quenching mechanism. The synthesized conjugates were successfully applied in protein labeling experiments

Organic & Biomolecular Chemistry published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C10H6Br2, Safety of (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Allott, Louis published the artcileRadiolabelling an ¹⁸F biologic via facile IEDDA “click” chemistry on the GE FASTLab platform, Recommanded Product: (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, the publication is Reaction Chemistry & Engineering (2021), 6(6), 1070-1078, database is CAplus and MEDLINE.

The use of biologics in positron emission tomog. (PET) imaging is an important area of radiopharmaceutical development and new automated methods are required to facilitate their production We report an automated radiosynthesis method to produce a radiolabeled biol. via facile inverse electron demand Diels-Alder (IEDDA) “click” chem. on a single GE FASTLab cassette. We exemplified the method by producing a fluorine-18 radiolabeled interleukin-2 (IL2) radioconjugate from a trans-cyclooctene (TCO) modified IL2 precursor. The radioconjugate was produced using a fully automated radiosynthesis on a single FASTLab cassette in a decay-corrected radiochem. yield (RCY, d.c.) of 19.8 ± 2.6% in 110 min (from start of synthesis); the molar activity was 132.3 ± 14.6 GBq μmol^-1. The in vitro uptake of [¹⁸F]TTCO-IL2 correlated with the differential receptor expression (CD25, CD122, CD132) in PC3, NK-92 and activated human PBMCs. The automated method may be adapted for the radiosynthesis of any TCO-modified protein via IEDDA chem.

Reaction Chemistry & Engineering published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, Recommanded Product: (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Asare-Okai, P. N. published the artcileSite-specific fluorescence labelling of RNA using bio-orthogonal reaction of trans-cyclooctene and tetrazine, SDS of cas: 1466420-02-9, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(58), 7844-7847, database is CAplus and MEDLINE.

This communication describes a general approach for site-specific fluorescence labeling of RNA using a cytidine triphosphate (CTP) analog derivatized with a trans-cyclooctene group. The analog was efficiently incorporated into a model RNA strand using in vitro transcription. Bio-orthogonal reaction with fluorescein-labeled tetrazine was utilized to fluorescently tag the synthetic RNA strand.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, SDS of cas: 1466420-02-9.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia