6-Maleimidocaproic acid - CAS 55750-53-3

6-Maleimidocaproic acid - CAS 55750-53-3 Catalog number: BADC-01624

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6-Maleimidocaproic acid can be used as a spacer group to construct drugs and other types of biological conjugals. 6-maleimide hexanoic acid and N-hydroxysuccinimide were used as bifunctional cross-linking reagent. It can also be used as a probe for mercaptan group (SH-group) in membrane protein.

Category
ADCs Linker
Product Name
6-Maleimidocaproic acid
CAS
55750-53-3
Catalog Number
BADC-01624
Molecular Formula
C10H13NO4
Molecular Weight
211.21
6-Maleimidocaproic acid

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Description
6-Maleimidocaproic acid can be used as a spacer group to construct drugs and other types of biological conjugals. 6-maleimide hexanoic acid and N-hydroxysuccinimide were used as bifunctional cross-linking reagent. It can also be used as a probe for mercaptan group (SH-group) in membrane protein.
Synonyms
2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic Acid; 6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic Acid; 6-Maleimidohexanoic Acid; N-(5-Carboxy-n-pentyl)maleimide; N-(5-Carboxypentyl)maleimide; ε-Maleimidocaproic Acid; ε-Maleimidohexanoic Acid; EMCA; Maleimide-(CH2)5-COOH; N-Maleoyl-6-aminocaproic acid; N-(6-oxo-6-hydroxyhexyl)maleimide; ZINC1542863; 6-maleimide hexanoic acid
IUPAC Name
6-(2,5-dioxopyrrol-1-yl)hexanoic acid
Canonical SMILES
C1=CC(=O)N(C1=O)CCCCCC(=O)O
InChI
InChI=1S/C10H13NO4/c12-8-5-6-9(13)11(8)7-3-1-2-4-10(14)15/h5-6H,1-4,7H2,(H,14,15)
InChIKey
WOJKKJKETHYEAC-UHFFFAOYSA-N
Density
1.285±0.06 g/cm3 (Predicted)
Solubility
Soluble in Water, Methanol, Ethanol, Dimethyl Sulfoxide; Insoluble in Ether; Slightly soluble in DMSO, Ethyl Acetate
Melting Point
86-91 °C
Flash Point
>230 °F
LogP
0.49430
Appearance
Off-white to white solid
Purity
98 % (HPLC)
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
2-8 °C
Signal Word
Danger
Boiling Point
407.3±28.0 °C (Predicted)

6-Maleimidocaproic acid is a versatile chemical compound mainly used in biochemical and biomedical applications. Here are some key applications of 6-Maleimidocaproic acid:

Protein Labeling: 6-Maleimidocaproic acid is widely used for labeling proteins with fluorescent dyes, enzymes, or other molecules. Its maleimide group reacts specifically with thiol groups on cysteine residues, forming stable thioether bonds. This allows researchers to track or quantify proteins in various biochemical assays and imaging studies.

Antibody-Drug Conjugates: In the development of antibody-drug conjugates (ADCs), 6-Maleimidocaproic acid serves as a linker molecule. It connects a potent cytotoxic drug to an antibody that targets cancer cells. This precise linkage ensures that the therapeutic payload is delivered specifically to cancer cells, minimizing side effects on healthy tissues.

Surface Modification: 6-Maleimidocaproic acid can be used to modify surfaces of biomaterials and nanomaterials with thiol-reactive groups. By functionalizing surfaces with specific proteins or ligands, it enhances their biocompatibility and specificity for biomedical applications such as biosensors, medical implants, and targeted drug delivery systems.

Peptide Synthesis: In peptide synthesis, 6-Maleimidocaproic acid is employed as a crosslinking agent to form stable peptide conjugates. By reacting with thiol groups in peptide chains, it helps in creating cyclic peptides or multidomain peptide structures. This is particularly useful in developing peptide-based therapeutics and studying protein-protein interactions.

1. Preparation, characterization and in vitro activity of a docetaxel-albumin conjugate
Jing Gao, Shougang Jiang, Xuewei Zhang, Yujie Fu, Zhiguo Liu Bioorg Chem. 2019 Mar;83:154-160. doi: 10.1016/j.bioorg.2018.10.032. Epub 2018 Oct 17.
Docetaxel is one of the most effective anticancer drugs. However, the current formulation of docetaxel contains Tween 80 and ethanol as the solvent, which can cause severe side effects. Consequently, the development of new type of formulation of docetaxel with high efficiency and low side effects is a very important issue. In this study, we explored the covalent linking of docetaxel and albumin via one organic linker. 6-Maleimidocaproic acid was applied to link the C2' hydroxyl group of docetaxel with the cysteine-34 of albumin to obtain 1:1 docetaxel-albumin conjugate. The synthesized conjugate can control the release of docetaxel in the bovine serum. Furthermore, in vitro cell cytotoxicity experiments indicated that the docetaxel-albumin conjugate have high activities for human prostate cancer cell line PC3 and human breast cancer cell line MCF-7. The present study provides a valuable strategy for further development of a new type of docetaxel-albumin prodrug.
2. iRGD-paclitaxel conjugate nanoparticles for targeted paclitaxel delivery
Hang Hu, Bin Wang, Chao Lai, Xiangjian Xu, Zihan Zhen, Huan Zhou, Defeng Xu Drug Dev Res. 2019 Dec;80(8):1080-1088. doi: 10.1002/ddr.21589. Epub 2019 Aug 14.
Paclitaxel (PTX) is a chemotherapeutic agent which shows antitumor activities against a broad spectrum of cancers. Yet, the current formulation of PTX used in clinic may cause a number of adverse reactions, which significantly limit its application. To obtain better clinical use of PTX, we report, for the first time, iRGD-PTX conjugate nanoparticles (NPs) for targeted PTX delivery. iRGD-PTX conjugate was synthesized from thiolated iRGD and 6-maleimidocaproic acid-PTX through Michael addition reaction. iRGD-PTX NPs with hydrodynamic diameter of ~110 nm were self-assembled from iRGD-PTX conjugate in deionized water. The as-prepared iRGD-PTX NPs exhibit good stability in phosphate buffered saline (PBS) buffer and fetal bovine serum containing PBS buffer. iRGD-PTX NPs exhibit sustained drug release behaviors. The in vitro studies show that iRGD-PTX NPs can be internalized by 4T1 cells by integrin αV-mediated endocytosis, resulting in better in vitro antitumor activity as compared to free PTX. The in vivo studies demonstrate that iRGD-PTX NPs exhibit enhanced tumor accumulation. The iRGD-PTX NPs reported here represent a novel PTX nanoplatform to achieve targeted PTX delivery.
3. Albumin-binding prodrugs of camptothecin and doxorubicin with an Ala-Leu-Ala-Leu-linker that are cleaved by cathepsin B: synthesis and antitumor efficacy
Björn Schmid, Da-Eun Chung, André Warnecke, Iduna Fichtner, Felix Kratz Bioconjug Chem. 2007 May-Jun;18(3):702-16. doi: 10.1021/bc0602735. Epub 2007 Mar 23.
We have recently validated a macromolecular prodrug strategy for improved cancer chemotherapy based on two features: (a) rapid and selective binding of thiol-reactive prodrugs to the cysteine-34 position of endogenous albumin and (b) acid-sensitive promoted or enzymatic release of the drug at the tumor site [Kratz, F., Warnecke, A., Scheuemann, K., Stockmar, C., Schwab, J., Lazar, P., Druckes, P., Esser, N., Drevs, J., Rognan, D., Bissantz, C., Hinderling, C., Folkers, G., Fichtner, I., and Unger, C. (2002) J. Med. Chem. 45, 5523-33]. In the present work, we developed water-soluble camptothecin (CPT) and doxorubicin (DOXO) prodrugs that incorporate the peptide linker Ala-Leu-Ala-Leu that serves as a substrate for the tumor-associated protease, cathepsin B, which is overexpressed in several solid tumors. Consequently, two albumin-binding prodrugs were synthesized [EMC-Arg-Arg-Ala-Leu-Ala-Leu-Ala-CPT (1) and EMC-Arg-Arg-Ala-Leu-Ala-Leu-DOXO (2) (EMC = 6-maleimidocaproic acid)]. Both prodrugs exhibited excellent water-solubility and bound rapidly and selectively to the cysteine-34 position of endogenous albumin. Further in vitro studies showed that the albumin-bound form of the prodrugs was cleaved specifically by cathepsin B as well as in human tumor homogenates. Major cleavage products were CPT-peptide derivatives and CPT for the CPT prodrug and H-Leu-Ala-Leu-DOXO, H-Leu-DOXO, and DOXO for the doxorubicin prodrug. In vivo, 1 was superior to free camptothecin in an HT-29 human colon xenograft model; the antitumor efficacy of prodrug 2 was comparable to that of free doxorubicin in the M-3366 mamma carcinoma xenograft model at equimolar doses.
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

Historical Records: 6-Maleimidocaproic acid
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