N-(Iodoacetamido)-Doxorubicin - CAS 114390-30-6

N-(Iodoacetamido)-Doxorubicin - CAS 114390-30-6 Catalog number: BADC-00892

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N-(Iodoacetamido)-Doxorubicin is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).

Category
ADCs Linker
Product Name
N-(Iodoacetamido)-Doxorubicin
CAS
114390-30-6
Catalog Number
BADC-00892
Molecular Formula
C29H30INO12
Molecular Weight
711.45
Purity
98.0%

Ordering Information

Catalog Number Size Price Quantity
BADC-00892 -- $-- Inquiry
Description
N-(Iodoacetamido)-Doxorubicin is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).
Synonyms
N-iodoacetyladriamycin
IUPAC Name
N-[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]-2-iodoacetamide
Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)NC(=O)CI)O
InChI
InChI=1S/C29H30INO12/c1-11-24(35)14(31-18(34)9-30)6-19(42-11)43-16-8-29(40,17(33)10-32)7-13-21(16)28(39)23-22(26(13)37)25(36)12-4-3-5-15(41-2)20(12)27(23)38/h3-5,11,14,16,19,24,32,35,37,39-40H,6-10H2,1-2H3,(H,31,34)/t11-,14-,16-,19-,24+,29-/m0/s1
InChIKey
SAGBOHNSGVDWII-MUTSDZRXSA-N
Solubility
10 mm in DMSO
Shelf Life
0-4 °C for short term (days to weeks), or -20 °C for long term (months).
Shipping
Room temperature
Storage
-20°C

N-(Iodoacetamido)-Doxorubicin is a conjugated molecule combining the well-known chemotherapeutic agent doxorubicin with an iodoacetamide functional group. The iodoacetamide group is a reactive electrophilic moiety that can form covalent bonds with thiol groups, such as those found on cysteine residues in proteins. This conjugation provides a unique approach for targeted drug delivery, enhancing the specificity and efficacy of doxorubicin in treating various cancers while minimizing its systemic toxicity. This compound offers important applications in cancer therapy, molecular biology, and targeted drug delivery systems.

One of the primary applications of N-(Iodoacetamido)-Doxorubicin is in the development of targeted cancer therapies. The iodoacetamido group allows the compound to form covalent bonds with thiol-containing proteins, including those on the surface of cancer cells or within their intracellular environment. By specifically attaching to proteins that are overexpressed or uniquely present in cancerous tissues, N-(Iodoacetamido)-Doxorubicin can deliver doxorubicin directly to the tumor site. This targeted delivery minimizes the off-target effects associated with traditional chemotherapy and improves the therapeutic index of doxorubicin, potentially leading to better clinical outcomes in cancer treatment.

In addition to its role in targeted cancer therapies, N-(Iodoacetamido)-Doxorubicin has applications in cancer cell research. Researchers can use this conjugated molecule to study the interactions between doxorubicin and specific cellular proteins. By labeling proteins with iodoacetamide, scientists can track how doxorubicin interacts with cellular components such as DNA, mitochondria, or specific protein targets involved in apoptosis. This makes N-(Iodoacetamido)-Doxorubicin an essential tool for understanding the molecular mechanisms of action of doxorubicin and for uncovering novel cancer drug targets.

N-(Iodoacetamido)-Doxorubicin can also be utilized in drug discovery and development. The ability to conjugate doxorubicin with a reactive functional group like iodoacetamide provides a valuable strategy for designing prodrugs or drug conjugates that can selectively release the active drug in response to specific biochemical conditions. This could lead to the creation of more effective drugs with reduced side effects. By attaching the iodoacetamide group to other therapeutic agents or nanoparticles, the compound could be used to create novel drug delivery systems that release doxorubicin in response to the presence of particular enzymes or other cellular markers, allowing for more precise treatment of various cancers.

Another important application of N-(Iodoacetamido)-Doxorubicin is in the development of bioconjugates for imaging and diagnostic purposes. The iodoacetamido group can facilitate the attachment of doxorubicin to imaging agents, such as fluorescent dyes or radiolabels. This enables the creation of dual-functional molecules that can be used for both therapeutic and diagnostic purposes, known as theranostic agents. By incorporating these molecules into imaging modalities like PET or MRI, clinicians can track the distribution of doxorubicin in the body and monitor the tumor response to treatment. This application has the potential to improve personalized cancer therapy by providing real-time insights into drug delivery and treatment effectiveness.

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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