MC-Val-Cit-PAB-tubulysin5a - CAS 2055896-86-9

MC-Val-Cit-PAB-tubulysin5a - CAS 2055896-86-9 Catalog number: BADC-00631

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MC-Val-Cit-PAB-tubulysin5a is a drug-linker conjugate for ADC with potent antitumor activity by using tubulysin5a (a tubulin inhibitor), linked via the ADC linker MC-Val-Cit-PAB.

Category
ADCs Cytotoxin with Linkers
Product Name
MC-Val-Cit-PAB-tubulysin5a
CAS
2055896-86-9
Catalog Number
BADC-00631
Molecular Formula
C66H96N11O13S
Molecular Weight
1283.6
MC-Val-Cit-PAB-tubulysin5a

Ordering Information

Catalog Number Size Price Quantity
BADC-00631 -- $-- Inquiry
Description
MC-Val-Cit-PAB-tubulysin5a is a drug-linker conjugate for ADC with potent antitumor activity by using tubulysin5a (a tubulin inhibitor), linked via the ADC linker MC-Val-Cit-PAB.
Synonyms
MC Val Cit PAB tubulysin5a
IUPAC Name
(2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-3-[[(2S,3S)-2-[[(2R)-1-[[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl]-1-methylpiperidin-1-ium-2-carbonyl]amino]-3-methylpentanoyl]-methylamino]-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoic acid
Canonical SMILES
CC(O[C@@H](C1=NC(C(N[C@H](C[C@H](C)C(O)=O)CC2=CC=CC=C2)=O)=CS1)C[C@H](C(C)C)N(C)C([C@@]([C@@H](C)CC)([H])NC([C@@H]3[N+](C)(CCCC3)CC4=CC=C(NC([C@H](CCCNC(N)=O)NC([C@H](C(C)C)NC(CCCCCN5C(C=CC5=O)=O)=O)=O)=O)C=C4)=O)=O)=O
InChI
InChI=1S/C66H95N11O13S/c1-11-42(6)58(64(86)75(9)51(40(2)3)37-53(90-44(8)78)63-72-50(39-91-63)60(83)70-48(35-43(7)65(87)88)36-45-21-14-12-15-22-45)74-61(84)52-24-17-19-34-77(52,10)38-46-26-28-47(29-27-46)69-59(82)49(23-20-32-68-66(67)89)71-62(85)57(41(4)5)73-54(79)25-16-13-18-33-76-55(80)30-31-56(76)81/h12,14-15,21-22,26-31,39-43,48-49,51-53,57-58H,11,13,16-20,23-25,32-38H2,1-10H3,(H8-,67,68,69,70,71,73,74,79,82,83,84,85,87,88,89)/p+1/t42-,43-,48+,49-,51+,52+,53+,57-,58-,77?/m0/s1
Shipping
Room temperature, or blue ice upon request.

MC-Val-Cit-PAB-tubulysin5a is a potent targeted drug conjugate that combines the highly cytotoxic compound tubulysin5a with a peptide linker (MC-Val-Cit-PAB). Tubulysin5a is a member of the tubulysin class of antimitotic agents, which disrupt microtubule dynamics and prevent proper cell division, leading to cancer cell death. The MC-Val-Cit-PAB linker is designed to release tubulysin5a specifically at the tumor site, minimizing its systemic toxicity and enhancing its therapeutic potential in cancer treatment. This conjugate offers a targeted approach, improving the efficacy and safety of tubulysin-based therapies.

One key application of MC-Val-Cit-PAB-tubulysin5a is in the treatment of solid tumors. Tubulysin5a's mechanism of action involves inhibition of microtubule polymerization, which effectively halts cell division and induces apoptosis in rapidly dividing tumor cells. The MC-Val-Cit-PAB linker ensures that tubulysin5a is activated only in the tumor microenvironment, where specific proteases cleave the peptide linker, releasing the drug directly at the site of cancer cells. This targeted delivery reduces off-target effects on healthy tissues and enhances the drug's antitumor activity, making it a promising approach for the treatment of solid cancers such as breast, lung, and colon cancers.

MC-Val-Cit-PAB-tubulysin5a also holds promise for overcoming drug resistance in cancer therapy. Many cancers develop resistance to conventional chemotherapies, including those targeting microtubules, through various mechanisms such as drug efflux or changes in the microtubule network. By using a targeted drug delivery system, MC-Val-Cit-PAB-tubulysin5a ensures that the cytotoxic agent is specifically delivered to the tumor cells, even in cases of resistance. This approach allows for more effective treatment of resistant cancer strains, improving therapeutic outcomes and offering a potential solution for patients with limited treatment options.

In addition, MC-Val-Cit-PAB-tubulysin5a can be utilized in combination therapies to enhance treatment efficacy. By combining tubulysin5a with other targeted therapies, such as immune checkpoint inhibitors or other chemotherapy agents, the conjugate could improve the overall therapeutic response. The specificity of the MC-Val-Cit-PAB linker ensures that tubulysin5a is only released at the site of action, while combination therapies can work synergistically to attack tumors through multiple pathways. This combination approach may reduce the likelihood of tumor relapse and improve patient survival rates.

1.Targeted drug delivery through the traceless release of tertiary and heteroaryl amines from antibody-drug conjugates
Staben LR, et al.
The reversible attachment of a small-molecule drug to a carrier for targeted delivery can improve pharmacokinetics and the therapeutic index. Previous studies have reported the delivery of molecules that contain primary and secondary amines via an amide or carbamate bond; however, the ability to employ tertiary-amine-containing bioactive molecules has been elusive. Here we describe a bioreversible linkage based on a quaternary ammonium that can be used to connect a broad array of tertiary and heteroaryl amines to a carrier protein. Using a concise, protecting-group-free synthesis we demonstrate the chemoselective modification of 12 complex molecules that contain a range of reactive functional groups. We also show the utility of this connection with both protease-cleavable and reductively cleavable antibody-drug conjugates that were effective and stable in vitro and in vivo. Studies with a tertiary-amine-containing antibiotic show that the resulting antibody-antibiotic conjugate provided appropriate stability and release characteristics and led to an unexpected improvement in activity over the conjugates previously connected via a carbamate.
The molarity calculator equation

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The dilution calculator equation

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This equation is commonly abbreviated as: C1V1 = C2V2

Historical Records: MC-Val-Cit-PAB-tubulysin5a
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