Name: Lys(MMT)-PAB-oxydiacetamide-PEG8-N3
Brand: BOC Sciences
Rating: 5 (1 reviews)

IUPAC Name

(2S)-2-[[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethoxy]acetyl]amino]-N-[4-(hydroxymethyl)phenyl]-6-[[(4-methoxyphenyl)-diphenylmethyl]amino]hexanamide

Canonical SMILES

COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)NCCCCC(C(=O)NC4=CC=C(C=C4)CO)NC(=O)COCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

InChI

InChI=1S/C55H77N7O14/c1-67-50-21-17-48(18-22-50)55(46-10-4-2-5-11-46,47-12-6-3-7-13-47)58-23-9-8-14-51(54(66)60-49-19-15-45(42-63)16-20-49)61-53(65)44-76-43-52(64)57-24-26-68-28-30-70-32-34-72-36-38-74-40-41-75-39-37-73-35-33-71-31-29-69-27-25-59-62-56/h2-7,10-13,15-22,51,58,63H,8-9,14,23-44H2,1H3,(H,57,64)(H,60,66)(H,61,65)/t51-/m0/s1

InChIKey

PKUIBTBLKQVEJS-XHIZWQFQSA-N

Appearance

Off-white to light yellow Oil

Lys(MMT)-PAB-oxydiacetamide-PEG8-N3 is a multifunctional compound designed for use in the development of advanced bioconjugation strategies. The compound incorporates several key components: lysine (Lys) as a reactive site, MMT (4-methyltriazolylmethoxy) as a protecting group, PAB (para-aminobenzyl) for linker chemistry, and PEG8 (a polyethylene glycol chain) to enhance solubility and improve pharmacokinetics. The compound also contains an azide group (N3), which enables click chemistry reactions for efficient conjugation to a wide range of biomolecules, such as proteins, peptides, or antibodies. This unique structure makes Lys(MMT)-PAB-oxydiacetamide-PEG8-N3 useful for creating targeted drug delivery systems and developing antibody-drug conjugates (ADCs).

One of the primary applications of Lys(MMT)-PAB-oxydiacetamide-PEG8-N3 is in the field of bioconjugation, particularly for the synthesis of antibody-drug conjugates (ADCs). The azide group allows for click chemistry-based attachment of drugs or other therapeutic agents to antibodies or other targeting molecules. The PEG8 spacer provides flexibility and steric shielding, which is crucial for reducing immunogenicity and enhancing the stability of the conjugate. By linking a cytotoxic payload or biologically active agent to the targeting antibody, Lys(MMT)-PAB-oxydiacetamide-PEG8-N3 can facilitate precise drug delivery to specific cells, such as cancer cells, reducing off-target effects and improving treatment efficacy.

Lys(MMT)-PAB-oxydiacetamide-PEG8-N3 also plays a significant role in the development of imaging agents for diagnostic purposes. The azide group is reactive in bioorthogonal reactions, allowing for the conjugation of imaging probes or fluorescent markers to targeting molecules. This enables the visualization of specific cells or tissues in vivo through non-invasive imaging techniques, such as positron emission tomography (PET) or fluorescence imaging. This application is especially valuable for studying disease progression, monitoring the effectiveness of therapies, or guiding surgical resection of tumors.

Another potential application of Lys(MMT)-PAB-oxydiacetamide-PEG8-N3 is in the creation of personalized medicine strategies. By using the click chemistry approach, drugs can be conjugated to a patient’s specific biomarkers or therapeutic targets, ensuring that the drug delivery is tailored to individual patients. This strategy can lead to more effective and safer treatments, particularly in oncology, where targeting specific tumor markers is crucial for improving outcomes. The versatility and efficiency of the compound make it a valuable tool in precision medicine and drug development.