Name: MC-Val-Cit-PAB-tubulysin5a
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

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.

Catalog	Product Name	CAS
BADC-01535	MC-VC-PAB-Tubulysin M	1639939-56-2
BADC-00625	Nitro-PDS-Tubulysin M	1941168-69-9
BADC-00184	Tubulysin A	205304-86-5
BADC-00345	Tubulysin B	205304-87-6
BADC-00360	Tubulysin M	936691-46-2
BADC-00719	Tubulysin IM-1
BADC-00720	Tubulysin IM-2
BADC-00721	Tubulysin IM-3