2,5-dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate - CAS 1214319-94-4

2,5-dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate - CAS 1214319-94-4 Catalog number: BADC-00429

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2,5-Dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate is a compound widely employed within the biomedical sector and exhibits promising implications for diverse maladies and ailments. Owing to its exceptional ability to target distinct drug receptors and pathways, this chemical entity unveils itself as a prospective therapeutic agent.

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Product Name
2,5-dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate
CAS
1214319-94-4
Catalog Number
BADC-00429
Molecular Formula
C16H24N2O7
Molecular Weight
356.37
2,5-dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate

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Description
2,5-Dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate is a compound widely employed within the biomedical sector and exhibits promising implications for diverse maladies and ailments. Owing to its exceptional ability to target distinct drug receptors and pathways, this chemical entity unveils itself as a prospective therapeutic agent.
Synonyms
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-(prop-2-ynylamino)ethoxy]ethoxy]ethoxy]propanoate;
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-(prop-2-ynylamino)ethoxy]ethoxy]ethoxy]propanoate
Canonical SMILES
C#CCNCCOCCOCCOCCC(=O)ON1C(=O)CCC1=O
InChI
InChI=1S/C16H24N2O7/c1-2-6-17-7-9-23-11-13-24-12-10-22-8-5-16(21)25-18-14(19)3-4-15(18)20/h1,17H,3-13H2
InChIKey
CHLIFODILFXXNH-UHFFFAOYSA-N
Appearance
Soild powder
Purity
≥98%
Shipping
Room temperature

2,5-Dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate, a synthetic compound with significant utility in biochemical and pharmaceutical research, finds diverse applications in the following realms characterized by high perplexity and burstiness:

Bioconjugation: Within bioconjugation reactions, this compound serves as a versatile tool for linking biomolecules, such as proteins and nucleic acids, to various surfaces or to each other. By establishing stable covalent bonds, it facilitates the exploration of protein interactions and the advancement of biosensor development, playing a pivotal role in diagnostic assays and targeted drug delivery systems.

Drug Development: In the realm of pharmaceutical research, 2,5-dioxopyrrolidin-1-yl 7,10,13-trioxa-4-azahexadec-1-yn-16-oate emerges as a crucial linker for synthesizing prodrugs and drug conjugates. Through the attachment of therapeutic agents to this linker, scientists enhance the bioavailability and precise delivery of drugs, leading to heightened efficacy and minimized side effects in treatment regimens.

Polymer Chemistry: This compound contributes significantly to the synthesis of functionalized polymers for diverse applications, including hydrogels and nanomaterials. Providing reactive sites that facilitate the grafting of biologically active components onto polymer frameworks, it proves essential in crafting responsive materials for medical devices and tissue engineering, showcasing its versatility and innovation potential.

Analytical Chemistry: In the realm of analytical biochemistry, this compound serves as a valuable tool for labeling biomolecules for detection and quantification purposes. By attaching fluorescent or other detectable markers, researchers can accurately monitor molecular interactions and reactions, enabling precise tracking in techniques such as fluorescence microscopy and mass spectrometry, highlighting its importance in advancing analytical methodologies.

1. MT477 acts in tumor cells as an AURKA inhibitor and strongly induces NRF-2 signaling
Kaoru Terai, Arkadiusz Z Dudek, Daniel Borja-Cacho, Piotr Jasinski, Rachel Isaksson Vogel, Pawel Zwolak Anticancer Res . 2011 Apr;31(4):1181-7.
Background:The novel compound thiopyrano [2,3-c]quinoline (MT477) has been shown to exhibit antitumor activity in both in vitro and in vivo studies. The present study examined the expression levels of 10,000 genes and how they changed after MT477 treatment in three cancer cell lines: H226, MDA231 and MiaPaCa-2. Materials and Methods/Results:Molecular function analysis revealed changes in genes involved in cell death, cell-cycle progression and cellular growth and proliferation in all three cancer cell lines. Canonical pathway analysis showed the involvement of the NRF2-mediated oxidative stress response, glucocorticoid, p53, RXR-VDR, G(1)/S checkpoint regulation, ERK, SAPK/JNK and JAS/Stat signaling. Analysis of 234 kinases and phosphatases using a kinase inhibition assay demonstrated a strong inhibitory effect for MAPK14 (104 ± 2%), AMPK A2/B1/G1 (89%) and FGR (83 ± 2%). AURKA was inhibited at 77 ± 1%. MiaPaCa-2 tumor xenograft studies showed a 49.5 ±1 4.8% inhibitory effect in mice treated with 100 μg/kg MT477 compared to untreated mice (p=0.0021).Conclusion:MT477 induces molecular mechanisms related to cell death, survival, and inhibition of cellular growth in vitro and in vivo.
2. Ultrasmall particles for Gd-MRI and (68) Ga-PET dual imaging
Vassilis Koutoulidis, Pascal Perriat, Penelope Bouziotis, Franck Denat, Olivier Tillement, Isabelle Bonnamour, Constantinos D Anagnostopoulos, Charles Truillet, Lucie Sancey, Frédéric Boschetti, François Lux, Thomas Brichart, Ulrich Darbost, Jérémy Brugière, Lia A Moulopoulos, Dimitris Stellas, Matteo Martini, Charalambos Tsoukalas Contrast Media Mol Imaging . 2015 Jul-Aug;10(4):309-19. doi: 10.1002/cmmi.1633.
Nanoparticles made of a polysiloxane matrix and surrounded by 1,4,7,10-tetraazacyclododecane-1-glutaric anhydride-4,7,10-triacetic acid (DOTAGA)[Gd(3+) ] and 2,2'-(7-(1-carboxy-4-((2,5-dioxopyrrolidin-1-yl)oxy)-4-oxobutyl)-1,4,7-triazonane-1,4-diyl)diacetic acid) NODAGA[(68) Ga(3+) ] have been synthesized for positron emission tomography/magnetic resonance (PET/MRI) dual imaging. Characterizations were carried out in order to determine the nature of the ligands available for radiolabelling and to quantify them. High radiolabelling purity (>95%) after (68) Ga labelling was obtained. The MR and PET images demonstrate the possibility of using the nanoparticles for a combined PET/MR imaging scanner. The images show fast renal elimination of the nanoparticles after intravenous injection.
3. Absolute quantification of peptides by isotope dilution liquid chromatography-inductively coupled plasma mass spectrometry and gas chromatography/mass spectrometry
Lu Yang, Xiandeng Hou, Rui Liu, Yi Lv, Margaret McCooeye, Zoltán Mester Anal Chem . 2013 Apr 16;85(8):4087-93. doi: 10.1021/ac400158u.
Absolute quantitation of peptides/proteins in dilute calibration solutions used in various diagnostic settings is a major challenge. Here we report the absolute quantitation of peptides by non-species-specific isotope dilution liquid chromatography-inductively coupled plasma mass spectrometry (ID LC-ICPMS) based on stoichiometric Eu tagging. The method was validated by species-specific isotope dilution gas chromatography/mass spectrometry (GC/MS) analysis of constituent amino acids of the target peptide. Quantitative labeling of bradykinin peptide was accomplished with a commercially available 2',2″-(10-(2-((2,5-dioxopyrrolidin-1-yl)oxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetic acid (DOTA-NHS-ester) and subsequently tagged with Eu. A (151)Eu-enriched spike was used for the non-species-specific ID LC-ICPMS determination of bradykinin. The non-species-specific ID LC-ICPMS method was cross-validated by a species-specific ID GC/MS approach, which is based on the determination of phenylalanine in bradykinin to derive the concentration of the peptide in the sample. The hydrolysis of the peptide into amino acids was achieved by microwave digestion with 4 M methanesulfonic acid, and derivatization of phenylalanine with methyl chloroformate (MCF) was performed prior to its detection by GC/MS based on a (13)C-enriched phenylalanine spike. The accuracy of the method was confirmed at various concentration levels with a typical precision of better than 5% relative standard deviation (RSD) at 20 pmol for non-species-specific ID LC-ICPMS and 500 pmol for species-specific ID GC/MS. A detection limit (3 SD) of 7.2 fmol estimated for ID LC-ICPMS with a 10 μL injection volume from three procedure blanks was obtained for bradykinin, confirming the suitability of the method for the direct determination of peptides at trace levels. To the best of our knowledge, the proposed method is the first ICPMS peptide quantification strategy which employs an independent validation strategy using species-specific ID GC/MS for amino acid quantitation.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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