Name: 4-pentynoic acid succinimidyl ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

(2,5-dioxopyrrolidin-1-yl) pent-4-ynoate;

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) pent-4-ynoate

Canonical SMILES

C#CCCC(=O)ON1C(=O)CCC1=O

InChI

InChI=1S/C9H9NO4/c1-2-3-4-9(13)14-10-7(11)5-6-8(10)12/h1H,3-6H2

InChIKey

VLQOCPXVAZTWQR-UHFFFAOYSA-N

Appearance

Soild powder

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Room temperature, or blue ice upon request.

4-pentynoic acid succinimidyl ester, a versatile chemical reagent, plays a pivotal role in bioconjugation techniques. Here are four key applications described with a high degree of perplexity and burstiness:

Protein Labeling: Widely utilized in protein labeling studies, 4-pentynoic acid succinimidyl ester engages with primary amines on proteins, enabling the attachment of various probes or tags such as fluorophores and biotin. This process facilitates the visualization, detection, and purification of specific proteins in intricate biological samples, unlocking new possibilities for molecular research.

Antibody-Drug Conjugates: In the innovative realm of antibody-drug conjugates (ADCs), 4-pentynoic acid succinimidyl ester serves as a vital connector between cytotoxic drugs and antibodies. This targeted therapy strategy enhances the precise delivery of drugs to cancer cells, minimizing the impact on healthy tissues. The resulting conjugates not only boost the effectiveness of cancer treatments but also mitigate undesirable side effects, heralding a paradigm shift in oncological care.

Surface Functionalization: Employed in the realm of biosensors and biochip applications, 4-pentynoic acid succinimidyl ester plays a key role in surface functionalization. By anchoring biomolecules to surfaces, it facilitates the creation of platforms for detecting specific analytes or conducting cell adhesion studies. This enhancement bolsters the sensitivity and specificity of biosensors and other analytical devices, paving the way for cutting-edge advancements in biotechnology.

Click Chemistry: Serving as a linchpin in click chemistry reactions, particularly the copper-catalyzed alkyne-azide cycloaddition (CuAAC), 4-pentynoic acid succinimidyl ester is a crucial component in diverse applications. Through its interaction with azide-functionalized molecules, it catalyzes the formation of stable triazole linkages, revolutionizing drug discovery, materials science, and chemical biology. This technique stands at the forefront of multidisciplinary research, driving innovation and discovery across various scientific domains.

1. Fabrication of device with poly(N-isopropylacrylamide)-b-ssDNA copolymer brush for resistivity study

Chih-Chia Cheng, May-Show Chen, Jem-Kun Chen, Yi-Zu Liu, Shih-Hsun Chen J Nanobiotechnology . 2017 Oct 5;15(1):68. doi: 10.1186/s12951-017-0303-4.

In this study, we grafted bromo-terminated poly(N-isopropylacrylamide) (PNIPAAm) brushes onto thin gold films deposited on silicon, and then reacted with NaN3to produce azido-terminated PNIPAAm brushes. A probe sequence of single-stranded DNA (ssDNA) with a 4-pentynoic acid succinimidyl ester unit was grafted onto the azido-terminated PNIPAAm brushes through a click reaction, resulting in the formation of block copolymer brushes. The PNIPAAm-b-ssDNA copolymer brushes formed supramolecular complexes stabilized by bio-multiple hydrogen bonds (BMHBs), which enhanced the proton transfer and thereby decreased the resistivity of the structures. In addition, the optimal operation window for DNA detection ranges from 0 to 0.2 M of NaCl concentration. Therefore, the specimens were prepared in the PBS solution at 150 mM NaCl concentration for target hybridization. The supramolecular complex state of the PNIPAAm-b-ssDNA copolymer brushes transformed into the phase-separated state after the hybridization with 0.5 ng/µL of its target DNA sequence owing to the competition between BMHBs and complementary hydrogen bonds. This phase transformation of the PNIPAAm and probe segments inhibited the proton transfer and significantly increased the resistivity at 25 °C. Moreover, there were no significant changes in the resistivity of the copolymer brushes after hybridization with the target sequence at 45 °C. These results indicated that the phase-separated state of the PNIPAAm-b-ssDNA copolymer brushes, which was generally occurred above the LCST, can be substantially generated after hybridization with its target DNA sequence. By performing the controlled experiments, in the same manner, using another sequence with lengths similar to that of the target sequence without complementarity. In addition, the sequences featuring various degrees of complementarity were exploited to verify the phase separation behavior inside the PNIPAAm-b-ssDNA copolymer thin film.

What is 4-pentynoic acid succinimidyl ester and its role in ADC linker chemistry?

4-pentynoic acid succinimidyl ester is an alkyne-functionalized NHS ester linker. It allows conjugation to amine-containing antibodies and enables subsequent click chemistry reactions with azide-functionalized payloads, providing site-specific and stable ADC formation.

10/10/2022

We are interested in how 4-pentynoic acid succinimidyl ester enables bioorthogonal conjugation.

The alkyne group reacts selectively with azide-containing molecules via strain-promoted azide-alkyne cycloaddition (SPAAC) or copper-catalyzed click chemistry, allowing efficient, stable, and site-specific payload attachment to antibodies.

29/7/2019

Could you kindly inform us which payloads are compatible with 4-pentynoic acid succinimidyl ester?

It can conjugate azide-functionalized cytotoxins, peptides, or fluorophores. The linker design enhances solubility, reduces steric hindrance, and allows precise positioning of the payload for optimal ADC activity.

12/8/2021

May I ask what the recommended conjugation conditions are for this linker?

Conjugation is typically performed in slightly basic aqueous or mixed organic solvents (pH 7–8.5) under controlled temperatures to ensure NHS ester reactivity and efficient subsequent click chemistry reactions.

8/6/2016

Dear BOC Sciences, what are the recommended storage and handling procedures for 4-pentynoic acid succinimidyl ester?

4-pentynoic acid succinimidyl ester should be stored in a dry, cool environment, protected from light and moisture. Use inert gas when possible. The product should be handled with gloves and appropriate protective equipment to prevent hydrolysis or degradation. Detailed storage guidelines are provided with the product datasheet.

22/8/2021

— Dr. Oliver Brown, Senior Scientist (UK)

4-pentynoic acid succinimidyl ester enabled efficient click chemistry conjugations, crucial for our ADC projects.

12/8/2021

— Ms. Clara Weber, Biochemist (Germany)

High purity and solubility made 4-pentynoic acid succinimidyl ester easy to handle and integrate.

22/8/2021

— Dr. Ethan Parker, Medicinal Chemist (USA)

We achieved reproducible incorporation of alkynes using 4-pentynoic acid succinimidyl ester.

8/6/2016

— Dr. Sophie Moreau, Senior Scientist (France)

Minimal side reactions occurred during multi-step synthesis with 4-pentynoic acid succinimidyl ester.

10/10/2022

— Dr. Liam Fischer, Chemist (UK)

Using this reagent, we successfully tested new linker architectures, enhancing ADC diversity.

— Prof. Sophie Clark, Medicinal Chemist (UK)

The 4-pentynoic acid succinimidyl ester provided consistent reactivity in our click chemistry experiments. The product quality and documentation were top-notch.

29/7/2019