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Mal-Phe-C4-VC-PAB-DMEA-PNU-159682

  CAS No.: 2259318-54-0   Cat No.: BADC-00867   Purity: ≥95% 4.5  

Mal-Phe-C4-VC-PAB-DMEA-PNU-159682, a drug-linker conjugate for ADC, consists the ADC linker Mal-Phe-C4-VC-PAB and a potent ADC cytotoxin DMEA-PNU-159682. DMEA-PNU-159682 includes metabolites of nemorubicin (MMDX) from liver microsomes and ADC cytotoxin PNU-159682.

Mal-Phe-C4-VC-PAB-DMEA-PNU-159682

Structure of 2259318-54-0

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Category
ADC Cytotoxin with Linker
Molecular Formula
C70H83N9O22
Molecular Weight
1402.46
Shipping
Room temperature
Storage
Store at -5°C,keep in dry and avoid sunlight.

* For research and manufacturing use only. We do not sell to patients.

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Synonyms
MPB-VC-PAB-DMEA-PNU159682; 4-((S)-2-((S)-2-(4-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)butanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl (2-oxo-2-((2S,4S)-2,5,12-trihydroxy-7-methoxy-4-(((1S,3R,4aS,9S,9aR,10aS)-9-methoxy-1-methyloctahydro-1H-pyrano[4',3':4,5]oxazolo[2,3-c][1,4]oxazin-3-yl)oxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)ethyl) ethane-1,2-diylbis(methylcarbamate); N-{4-[4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]butanoyl}-L-valyl-N5-carbamoyl-N-(4-{4,7-dimethyl-3,8,11-trioxo-11-[(2S,4S)-2,5,12-trihydroxy-7-methoxy-4-{[(1S,3R,4aS,9S,9aR,10aS)-9-methoxy-1-methyloctahydro-1H-pyrano[4',3':4,5][1,3]oxazolo[2,3-c][1,4]oxazin-3-yl]oxy}-6,11-dioxo-1,2,3,4,6,11-hexahydro-2-tetracenyl]-2,9-dioxa-4,7-diazaundec-1-yl}phenyl)-L-ornithinamide
IUPAC Name
[2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-7-methoxy-4-[[(2S,4R,6S,7S,9R,10S)-10-methoxy-6-methyl-5,8,11-trioxa-1-azatricyclo[7.4.0.02,7]tridecan-4-yl]oxy]-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl] N-[2-[[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[4-[4-(2,5-dioxopyrrol-1-yl)phenyl]butanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methoxycarbonyl-methylamino]ethyl]-N-methylcarbamate
Canonical SMILES
CC1C2C(CC(O1)OC3CC(CC4=C3C(=C5C(=C4O)C(=O)C6=C(C5=O)C(=CC=C6)OC)O)(C(=O)COC(=O)N(C)CCN(C)C(=O)OCC7=CC=C(C=C7)NC(=O)C(CCCNC(=O)N)NC(=O)C(C(C)C)NC(=O)CCCC8=CC=C(C=C8)N9C(=O)C=CC9=O)O)N1CCOC(C1O2)OC
InChI
InChI=1S/C70H83N9O22/c1-36(2)57(75-49(81)15-8-11-38-18-22-41(23-19-38)79-50(82)24-25-51(79)83)64(89)74-44(13-10-26-72-67(71)90)63(88)73-40-20-16-39(17-21-40)34-97-68(91)76(4)27-28-77(5)69(92)98-35-48(80)70(93)32-43-54(61(87)56-55(59(43)85)58(84)42-12-9-14-46(94-6)53(42)60(56)86)47(33-70)100-52-31-45-62(37(3)99-52)101-65-66(95-7)96-30-29-78(45)65/h9,12,14,16-25,36-37,44-45,47,52,57,62,65-66,85,87,93H,8,10-11,13,15,26-35H2,1-7H3,(H,73,88)(H,74,89)(H,75,81)(H3,71,72,90)/t37-,44-,45-,47-,52-,57-,62+,65+,66-,70-/m0/s1
InChIKey
MQEXMWGXCVPEOU-KYJWDNHDSA-N
Density
1.48±0.1 g/cm3
Solubility
Soluble in DMSO (10 mm)
Appearance
Solid
Shelf Life
0-4°C for short term (days to weeks), or -20°C for long term (months).
Shipping
Room temperature
Storage
Store at -5°C,keep in dry and avoid sunlight.
Form
Solid

Mal-Phe-C4-VC-PAB-DMEA-PNU-159682 is a highly specialized compound used primarily in the development of targeted drug delivery systems, including antibody-drug conjugates (ADCs) and peptide-drug conjugates (PDCs). The maleimide (Mal) group enables selective conjugation to thiol-containing molecules, such as antibodies or peptides, providing high specificity in bioconjugation. The Phe (phenylalanine) and VC (valine-citrulline) sequence acts as a cleavable linker, which is designed to release the cytotoxic payload only after reaching the target tissue, typically through enzymatic cleavage in the tumor microenvironment. The DMEA (dimethylaminoethyl) group enhances solubility and stability, ensuring better pharmacokinetics, while the PNU-159682 moiety represents a potent drug payload, further contributing to the effectiveness of the conjugate in targeted therapies.

One of the key applications of Mal-Phe-C4-VC-PAB-DMEA-PNU-159682 is in the creation of targeted antibody-drug conjugates (ADCs) for cancer treatment. The compound facilitates the attachment of cytotoxic drugs to monoclonal antibodies, which can specifically target tumor cells. The cleavable VC (valine-citrulline) linker ensures that the payload is released only within the tumor site, where enzymes present in the tumor microenvironment cleave the linker, activating the drug. This selective drug release minimizes systemic toxicity and increases the drug's therapeutic efficacy by directly targeting cancer cells. The DMEA group enhances solubility, improving the pharmacokinetics and circulation time of the ADC.

Mal-Phe-C4-VC-PAB-DMEA-PNU-159682 is also highly useful in the development of peptide-drug conjugates (PDCs), where peptide-based targeting agents are conjugated with cytotoxic drugs. In this application, the compound allows for precise drug delivery to specific tissues, such as tumors, by utilizing the tumor-targeting peptides. The cleavable VC linker ensures that the drug payload is selectively released at the target site, enhancing the precision of the treatment while reducing off-target effects. The DMEA group provides enhanced solubility, which aids in the stability and bioavailability of the conjugate, making it a highly efficient tool for targeted cancer therapy.

Additionally, Mal-Phe-C4-VC-PAB-DMEA-PNU-159682 can be employed in molecular imaging applications for disease diagnostics. By conjugating imaging agents, such as fluorescent dyes or radiolabels, to antibodies or peptides, the compound facilitates the targeted visualization of biomarkers associated with cancer or other diseases. The cleavable linker ensures that the imaging agent is only released at the target site, which improves the accuracy and sensitivity of the imaging process. The DMEA group further aids in ensuring the stability and prolonged circulation of the conjugate, making it a valuable tool for diagnostic imaging and precision medicine.

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

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Historical Records: m-PEG5-succinimidyl carbonate | Bis-PEG6-NHS ester | Bis-PEG17-NHS ester | Mal-PEG2-NHS ester | Mal-Phe-C4-VC-PAB-DMEA-PNU-159682
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