Name: Mal-PEG2-VCP-Eribulin
Brand: BOC Sciences
Rating: 5 (1 reviews)

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IUPAC Name

[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[3-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]propanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl N-[(2S)-2-hydroxy-3-[(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-21-methoxy-14-methyl-8,15-dimethylidene-24-oxo-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-20-yl]propyl]carbamate

Canonical SMILES

CC1CC2CCC3C(=C)CC(O3)CCC45CC6C(O4)C7C(O6)C(O5)C8C(O7)CCC(O8)CC(=O)CC9C(CC(C1=C)O2)OC(C9OC)CC(CNC(=O)OCC1=CC=C(C=C1)NC(=O)C(CCCNC(=O)N)NC(=O)C(C(C)C)NC(=O)CCOCCOCCN1C(=O)C=CC1=O)O

InChI

InChI=1S/C70H99N7O21/c1-37(2)59(76-56(80)20-24-88-26-27-89-25-23-77-57(81)17-18-58(77)82)67(84)75-49(8-7-22-72-68(71)85)66(83)74-42-11-9-41(10-12-42)36-90-69(86)73-35-44(79)32-54-60(87-6)48-31-43(78)30-46-14-16-51-61(93-46)65-64-63(95-51)62-55(96-64)34-70(97-62,98-65)21-19-47-29-39(4)50(91-47)15-13-45-28-38(3)40(5)52(92-45)33-53(48)94-54/h9-12,17-18,37-38,44-55,59-65,79H,4-5,7-8,13-16,19-36H2,1-3,6H3,(H,73,86)(H,74,83)(H,75,84)(H,76,80)(H3,71,72,85)/t38-,44+,45+,46-,47+,48+,49+,50+,51+,52-,53+,54-,55-,59+,60-,61+,62+,63+,64-,65+,70+/m1/s1

InChIKey

ODAGJGZILCZEBN-LHGNNKGASA-N

Solubility

10 mm in DMSO

Appearance

Solid

Shelf Life

0-4°C for short term (days to weeks), or -20°C for long term (months).

Shipping

Room temperature, or blue ice upon request.

Storage

Store at -20 °C, keep in dry and avoid sunlight.

Form

Solid

Biological Activity

Mal-PEG2-VCP-Eribulin consists the ADCs linker (Mal-PEG2-VCP) and Eribulin[1]. Eribulin is a mechanistically unique microtubule inhibitor for cancer[2]. Mal-PEG2-VCP-Eribulin is an Eribulin-based drug for antibody conjugates[1] .

Mal-PEG2-VCP-Eribulin is a sophisticated conjugate designed for targeted cancer therapy, combining the maleimide (Mal) group, a polyethylene glycol (PEG2) spacer, a VCP (Valine-Citrulline-PAB) linker, and the potent anticancer agent Eribulin. The maleimide group is highly reactive with thiol-containing molecules, such as antibodies, peptides, or proteins, enabling the stable conjugation of Eribulin to targeting biomolecules. The PEG2 spacer enhances the solubility, stability, and pharmacokinetics of the conjugate, facilitating efficient circulation and reducing non-specific interactions. The VCP linker is specifically cleaved by enzymes present in the tumor microenvironment, enabling controlled drug release at the target site. This targeted delivery of Eribulin improves therapeutic efficacy while minimizing systemic toxicity.

A key application of Mal-PEG2-VCP-Eribulin is in the development of antibody-drug conjugates (ADCs) for cancer treatment. Eribulin, a microtubule-targeting agent, is used in chemotherapy to inhibit cancer cell division, but its therapeutic potential can be limited by off-target toxicity and poor bioavailability. By conjugating Eribulin to monoclonal antibodies through the VCP linker, the drug can be specifically directed to tumor cells expressing certain surface antigens. The maleimide group ensures the stable attachment of the conjugate to the targeting antibody, while the PEG2 spacer provides improved solubility and circulation time. The VCP linker allows for selective cleavage at the tumor site, ensuring that Eribulin is released directly where it is needed, thereby enhancing therapeutic efficacy and reducing side effects.

Mal-PEG2-VCP-Eribulin is also used in the development of targeted therapies for drug-resistant cancers. Cancer cells can develop resistance to chemotherapies through mechanisms such as drug efflux or altered drug metabolism. By using a targeted delivery system like Mal-PEG2-VCP-Eribulin, it is possible to bypass some of these resistance mechanisms. The conjugate ensures that Eribulin is delivered specifically to the cancer cells, overcoming challenges such as poor cellular uptake or drug efflux pumps that typically limit chemotherapy effectiveness. This strategy enhances the cytotoxicity of Eribulin against resistant tumor cells, offering potential for more effective treatment of hard-to-treat cancers.

In addition to cancer therapy, Mal-PEG2-VCP-Eribulin can be applied in combination therapies to enhance the effectiveness of other anticancer treatments. The conjugate can be used alongside immunotherapies or targeted therapies to provide a multi-pronged approach to fighting cancer. For instance, Mal-PEG2-VCP-Eribulin can be combined with immune checkpoint inhibitors or other biological agents that enhance immune system recognition and destruction of tumor cells. This synergistic approach can potentially improve clinical outcomes by combining the benefits of targeted drug delivery with the immune system’s ability to fight cancer.