Category: 1395786-30-7

Marculescu, Cristina published the artcileProbing the limits of Q-tag bioconjugation of antibodies, Application of Dbco-maleimide, the publication is Chemical Communications (Cambridge, United Kingdom) (2019), 55(76), 11342-11345, database is CAplus and MEDLINE.

Site-selective labeling of antibodies (Abs) can circumvent problems from heterogeneity of conventional conjugation. Here, the authors evaluate the industrially-applied chemoenzymic ‘Q-tag’ strategy based on transglutaminase-mediated (TGase) amide-bond formation in the generation of ⁸⁹Zr-radiolabeled antibody conjugates. Despite previously suggested high regioselectivity of TGases, in the anti-Her2 Ab Herceptin more precise native MS indicates only 70-80% functionalization at the target site (Q298_H), in competition with modification at other sites, such as Q3_H critically close to the CDR1 region.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, Application of Dbco-maleimide.

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

Hirasawa, Shigeo published the artcileFacile and Efficient Chemoenzymatic Semisynthesis of Fc-Fusion Compounds for Half-Life Extension of Pharmaceutical Components, HPLC of Formula: 1395786-30-7, the publication is Bioconjugate Chemistry (2019), 30(9), 2323-2331, database is CAplus and MEDLINE.

The formation of Fc-fusions, in which biol. active mols. and the Fc fragment of antibodies are linked to each other, is one of the most efficient and successful half-life extension technologies to be developed and applied to peptide and protein pharmaceuticals thus far. Fc-fusion compounds are generally produced by recombinant methods. However, these cannot be applied to artificial middle mols., such as peptides with non-natural amino acids, unnatural cyclic peptides, or pharmaceutical oligonucleotides. Here, we developed a simple, efficient, semisynthetic method for Fc-fusion production involving our previously developed enzymic N-terminal extension reaction (i.e., NEXT-A reaction) and strain-promoted azide-alkyne cycloaddition, achieving quant. conversion and high selectivity for the N-terminus of the Fc protein. An Fc-fusion compound prepared by this method showed comparable biol. activity to that of the original peptide and a long-circulating plasma half-life. Thus, the proposed method is potentially applicable for the conjugation of a wide range of pharmaceutical components.

Bioconjugate Chemistry published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, HPLC of Formula: 1395786-30-7.

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

Chan, Leslie W. published the artcileSelective Permeabilization of Gram-Negative Bacterial Membranes Using Multivalent Peptide Constructs for Antibiotic Sensitization, Name: Dbco-maleimide, the publication is ACS Infectious Diseases (2021), 7(4), 721-732, database is CAplus and MEDLINE.

The drug-impermeable bacterial membrane in Gram-neg. pathogens limits antibiotic access to intracellular drug targets. To expand our rapidly waning antibiotic arsenal, one approach is to improve the intracellular delivery of drugs with historically poor accumulation in Gram-neg. bacteria. To do so, we engineered macromol. potentiators to permeabilize the Gram-neg. membrane to facilitate drug influx. Potentiators, known as WD40, were synthesized by grafting multiple copies of a cationic ¦Á-helical antimicrobial peptide, WLBU2, onto a dextran polymer scaffold. WD40 enabled drug uptake in the model pathogen P. aeruginosa, a capability that was not observed with unmodified WLBU2 peptide. WD40 was able to reduce min. inhibitory concentrations of a drug panel by up to 3 orders of magnitude. Hydrophobic and highly three-dimensional antibiotics exhibited the greatest potentiation. Antibiotic activity was potentiated in several clin. strains and resulted in sensitization of drug-resistant strains to rifampin, a drug not previously used for Gram-neg. infections.

ACS Infectious Diseases published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, Name: Dbco-maleimide.

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

Cheloha, Ross W. published the artcileImproved GPCR ligands from nanobody tethering, Name: Dbco-maleimide, the publication is Nature Communications (2020), 11(1), 2087, database is CAplus and MEDLINE.

Abstract: Antibodies conjugated to bioactive compounds allow targeted delivery of therapeutics to cell types of choice based on that antibody’s specificity. Here we develop a new type of conjugate that consists of a nanobody and a peptidic ligand for a G protein-coupled receptor (GPCR), fused via their C-termini. We address activation of parathyroid hormone receptor-1 (PTHR1) and improve the signaling activity and specificity of otherwise poorly active N-terminal peptide fragments of PTH by conjugating them to nanobodies (VHHs) that recognize PTHR1. These C-to-C conjugates show biol. activity superior to that of the parent fragment peptide in vitro. In an exploratory experiment in mice, a VHH-PTH peptide conjugate showed biol. activity, whereas the corresponding free peptide did not. The lead conjugate also possesses selectivity for PTHR1 superior to that of PTH(1-34). This design approach, dubbed “conjugation of ligands and antibodies for membrane proteins” (CLAMP), can yield ligands with high potency and specificity.

Nature Communications published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, Name: Dbco-maleimide.

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

Evans, Helen L. published the artcileBioorthogonal chemistry for ⁶⁸Ga radiolabelling of DOTA-containing compounds, Formula: C25H21N3O4, the publication is Journal of Labelled Compounds and Radiopharmaceuticals (2014), 57(4), 291-297, database is CAplus and MEDLINE.

Copper-catalyzed ‘click’ chem. is a highly used technique for radiolabeling small mols. and peptides for imaging applications. The usefulness of these reactions falls short, however, when metal catalysis is not a practically viable route; such as when using metal chelates as radioligands. Here, the authors describe a method for carrying out ‘click-type’ radiochem. in the presence of DOTA chelates, by combining ⁶⁸Ga radiolabeling techniques with well-established bioorthogonal reactions, which do not rely upon metal catalysis.

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, Formula: C25H21N3O4.

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

Cordonnier, Axel published the artcileSynthesis and in vitro preliminary evaluation of prostate-specific membrane antigen targeted upconversion nanoparticles as a first step towards radio/fluorescence-guided surgery of prostate cancer, HPLC of Formula: 1395786-30-7, the publication is Journal of Materials Chemistry B: Materials for Biology and Medicine (2021), 9(36), 7423-7434, database is CAplus and MEDLINE.

Over the last decade, upconversion nanoparticles (UCNP) have been widely investigated in nanomedicine due to their high potential as imaging agents in the near-IR (NIR) optical window of biol. tissues. Here, we successfully develop active targeted UCNP as potential probes for dual NIR-NIR fluorescence and radioactive-guided surgery of prostate-specific membrane antigen (PSMA)(+) prostate cancers. We designed a one-pot thermolysis synthesis method to obtain oleic acid-coated spherical NaYF₄:Yb,Tm@NaYF₄ core/shell UCNP with narrow particle size distribution (30.0 ¡À 0.1 nm, as estimated by SAXS anal.) and efficient upconversion luminescence. Polyethylene glycol (PEG) ligands bearing different anchoring groups (phosphate, bis- and tetra-phosphonate-based) were synthesized and used to hydrophilize the UCNP. DLS studies led to the selection of a tetra-phosphonate PEG(2000) ligand affording water-dispersible UCNP with sustained colloidal stability in several aqueous media. PSMA-targeting ligands (i.e., glutamate-urea-lysine derivatives called KuEs) and fluorescent or radiolabeled prosthetic groups were grafted onto the UCNP surface by strain-promoted azide-alkyne cycloaddition (SPAAC). These UCNP, coated with 10 or 100% surface d. of KuE ligands, did not induce cytotoxicity over 24 h incubation in LNCaP-Luc or PC3-Luc prostate cancer cell lines or in human fibroblasts for any of the concentrations evaluated. Competitive binding assays and flow cytometry demonstrated the excellent affinity of UCNP@KuE for PSMA-pos. LNCaP-Luc cells compared with non-targeted UCNP@CO₂H. Furthermore, the binding of UCNP@KuE to prostate tumor cells was pos. correlated with the surface d. of PSMA-targeting ligands and maintained after ¹²⁵I-radiolabelling. Finally, a preliminary biodistribution study in LNCaP-Luc-bearing mice demonstrated the radiochem. stability of non-targeted [^125I]UCNP paving the way for future in vivo assessments.

Journal of Materials Chemistry B: Materials for Biology and Medicine published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, HPLC of Formula: 1395786-30-7.

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

Al Temimi, Abbas H. K. published the artcilePeptide-appended permethylated β-cyclodextrins with hydrophilic and hydrophobic spacers, Name: Dbco-maleimide, the publication is Bioconjugate Chemistry (2017), 28(8), 2160-2166, database is CAplus and MEDLINE.

A novel synthetic methodol., employing a combination of the strain-promoted azide-alkyne cycloaddition and maleimide-thiol reactions, for the preparation of permethylated β-cyclodextrin-linker-peptidyl conjugates is reported. Two different bifunctional maleimide crosslinking probes, the polyethylene glycol containing hydrophilic linker bicyclo[6.1.0] nonyne-maleimide and the hydrophobic 5′-dibenzoazacyclooctyne-maleimide, were attached to azide-appended permethylated β-cyclodextrin. The successfully introduced maleimide function was exploited to covalently graft a cysteine-containing peptide (Ac-Tyr-Arg-Cys-Amide) to produce the target conjugates. The final target compounds were isolated in high purity after purification by isocratic preparative reverse-phase high-performance liquid chromatog. This novel synthetic approach is expected to give access to many different cyclodextrin-linker peptides.

Bioconjugate Chemistry published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, Name: Dbco-maleimide.

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

Tamura, Ryo published the artcilePhotoactivatable Prodrug of Doxazolidine Targeting Exosomes, Quality Control of 1395786-30-7, the publication is Journal of Medicinal Chemistry (2019), 62(4), 1959-1970, database is CAplus and MEDLINE.

Natural lipid nanocarriers, exosomes, carry cell-signaling materials such as DNA and RNA for intercellular communications. Exosomes derived from cancer cells contribute to the progression and metastasis of cancer cells by transferring oncogenic signaling mols. to neighboring and remote premetastatic sites. Therefore, applying the unique properties of exosomes for cancer therapy has been expected in science, medicine, and drug discovery fields. Herein, we report that an exosome-targeting prodrug system, designated MARCKS-ED-photodoxaz, could spatiotemporally control the activation of an exquisitely cytotoxic agent, doxazolidine (doxaz), with UV light. The MARCKS-ED peptide enters a cell by forming a complex with the exosomes in situ at its plasma membrane and in the media. MARCKS-ED-photodoxaz releases doxaz under near-UV irradiation to inhibit cell growth with low nanomolar IC₅₀ values. The MARCKS-ED-photodoxaz system targeting exosomes and utilizing photochem. will potentially provide a new approach for the treatment of cancer, especially for highly progressive and invasive metastatic cancers.

Journal of Medicinal Chemistry published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C8H6F3NO, Quality Control of 1395786-30-7.

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

Wang, Tao published the artcileEngineering immunomodulatory and osteoinductive implant surfaces via mussel adhesion-mediated ion coordination and molecular clicking, Quality Control of 1395786-30-7, the publication is Nature Communications (2022), 13(1), 160, database is CAplus and MEDLINE.

Immune response and new tissue formation are important aspects of tissue repair. However, only a single aspect is generally considered in previous biomedical interventions, and the synergistic effect is unclear. Here, a dual-effect coating with immobilized immunomodulatory metal ions (e.g., Zn²⁺) and osteoinductive growth factors (e.g., BMP-2 peptide) is designed via mussel adhesion-mediated ion coordination and mol. clicking strategy. Compared to the bare TiO₂ group, Zn²⁺ can increase M2 macrophage recruitment by up to 92.5% in vivo and upregulate the expression of M2 cytokine IL-10 by 84.5%; while the dual-effect of Zn²⁺ and BMP-2 peptide can increase M2 macrophages recruitment by up to 124.7% in vivo and upregulate the expression of M2 cytokine IL-10 by 171%. These benefits eventually significantly enhance bone-implant mech. fixation (203.3 N) and new bone ingrowth (82.1%) compared to the bare TiO2 (98.6 N and 45.1%, resp.). Taken together, the dual-effect coating can be utilized to synergistically modulate the osteoimmune microenvironment at the bone-implant interface, enhancing bone regeneration for successful implantation.

Nature Communications published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C8H6ClF, Quality Control of 1395786-30-7.

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

Perols, Anna published the artcileSite-Specific Antibody Labeling by Covalent Photoconjugation of Z Domains Functionalized for Alkyne-Azide Cycloaddition Reactions, SDS of cas: 1395786-30-7, the publication is ChemBioChem (2015), 16(17), 2522-2529, database is CAplus and MEDLINE.

Antibodies are extensively used in research, diagnostics, and therapy, and for many applications the antibodies need to be labeled. Labeling is typically performed by using amine-reactive probes that target surface-exposed lysine residues, resulting in heterogeneously labeled antibodies. An alternative labeling strategy is based on the IgG (IgG)-binding protein domain Z, which binds to the Fc region of IgG. Introducing the photoactivable amino acid benzoylphenylalanine (BPA) into the Z domain makes it possible for a covalent bond to be be formed between the Z domain and the antibody on UV irradiation, to produce a site-specifically labeled product. Z₃₂BPA was synthesized by solid-phase peptide synthesis and further functionalized to give alkyne-Z₃₂BPA and azide-Z₃₂BPA for Cu^I-catalyzed cycloaddition, as well as DBCO-Z₃₂BPA for Cu-free strain-promoted cycloaddition The Z₃₂BPA variants were conjugated to the human IgG1 antibody trastuzumab and site-specifically labeled with biotin or fluorescein. The fluorescently labeled trastuzumab showed specific staining of the membranes of HER2-expressing cells in immunofluorescence microscopy.

ChemBioChem published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, SDS of cas: 1395786-30-7.

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