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Dideoxy-amanitin

  CAS No.: 58255-46-2   Cat No.: BADC-01363 4.5  

Dideoxy-amanitin is an α-Amanitin derivative. α-Amanitin is an extremely toxic bicyclic octapeptide isolated from the death-cap mushroom, Amanita phalloides. As a potent inhibitor of RNA polymerase II, α-amanitin is toxic to eukaryotic cells.

Dideoxy-amanitin

Structure of 58255-46-2

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Category
ADC Cytotoxin
Molecular Formula
C39H54N10O12S
Molecular Weight
886.97
Storage
Store at 0-4°C for short term (days to weeks) or -20°C for long term (months to years)

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

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IUPAC Name
2-[(1R,4S,8R,10S,13S,16S,34S)-34-[(2S)-butan-2-yl]-13-[(2R,3R)-3,4-dihydroxybutan-2-yl]-8-hydroxy-2,5,11,14,30,33,36,39-octaoxo-27-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetamide
Canonical SMILES
CCC(C)C1C(=O)NCC(=O)NC2CSC3=C(CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)CC(=O)N)O)C(C)C(CO)O)C5=CC=CC=C5N3
InChI
InChI=1S/C39H54N10O12S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-62-38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)/t17-,18-,19+,23-,24-,25-,26-,27-,31-,32-/m0/s1
InChIKey
RXGJTYFDKOHJHK-KFGVHZSZSA-N
Storage
Store at 0-4°C for short term (days to weeks) or -20°C for long term (months to years)

Dideoxy-amanitin is a synthetic derivative of the naturally occurring amatoxin, alpha-amanitin. It functions as an ADC cytotoxin and is utilized as a payload in the development of antibody-drug conjugates for cancer therapy. This compound is engineered for efficient bioconjugation to antibodies, enabling the targeted delivery of its cytotoxic activity. As an ADC payload, Dideoxy-amanitin is incorporated into an ADC construct to achieve selective targeting of malignant cells while minimizing systemic exposure. Its properties support its use in the development of ADCs intended for precise tumor delivery.

The cytotoxic activity of Dideoxy-amanitin is attributed to its mechanism of action as an RNA polymerase II inhibitor. Upon internalization by the target cell via the antibody-drug conjugate, this ADC cytotoxin localizes to the nucleus, where it binds to and inhibits the function of RNA polymerase II. This inhibition leads to the subsequent shutdown of protein synthesis, ultimately resulting in cell cycle arrest and apoptosis. This cellular mechanism targets a process fundamental to cell function and proliferation, which is relevant in the context of pathways associated with multidrug resistance.

Dideoxy-amanitin is a compound used in bioconjugation research and tumor therapy. Its chemical structure provides stability and compatibility with various linker chemistries for creating payload-linker systems. For researchers and companies working on advancing the antibody-drug conjugate field, this compound serves as an alternative to other payloads. The compound's potency is a characteristic evaluated for its potential to improve the therapeutic efficacy of ADCs.

What is Dideoxy-amanitin?

Dideoxy-amanitin is a bicyclic peptide cytotoxin derived from Amanita species, used in ADC research. It selectively inhibits RNA polymerase II, preventing mRNA synthesis and leading to apoptosis. Its specificity makes it a valuable payload for targeted cancer therapy studies.

14/12/2018

We would like to know how Dideoxy-amanitin is used in ADC development.

Dideoxy-amanitin serves as a highly potent payload in ADCs. It is conjugated to antibodies targeting specific tumor antigens. After internalization, it inhibits transcription in cancer cells, inducing cell death while minimizing effects on non-target tissues.

12/4/2017

Could you share the main research applications of Dideoxy-amanitin?

Dideoxy-amanitin is employed in preclinical studies for oncology-focused ADCs. Researchers use it to evaluate the efficacy of transcription-inhibiting payloads, optimize linker chemistry, and study intracellular trafficking of conjugates for enhanced therapeutic outcomes.

22/12/2021

May I ask what the structural features of Dideoxy-amanitin are?

Dideoxy-amanitin is a bicyclic octapeptide lacking two hydroxyl groups, enhancing stability. Its structure allows selective binding to RNA polymerase II, making it suitable for incorporation into ADCs for precise delivery and controlled cytotoxic activity in cancer cells.

27/11/2020

Good afternoon! What safety considerations are required when working with Dideoxy-amanitin?

Due to its potent inhibitory effect on transcription, Dideoxy-amanitin requires careful handling. Laboratory personnel should follow biosafety guidelines, use appropriate protective equipment, and implement containment measures to prevent exposure during ADC synthesis and experimentation.

21/12/2020

— Dr. David Miller, Senior ADC Researcher (USA)

Dideoxy-amanitin delivered by BOC Sciences had excellent purity and stability. Technical guidance was very helpful.

22/12/2021

— Dr. Susan Mitchell, Oncology Scientist (USA)

Dideoxy-amanitin from BOC Sciences exhibited outstanding potency and reproducibility in our payload development assays.

21/12/2020

— Mr. Pierre Laurent, Research Scientist (France)

The compound was supplied with full analytical characterization, ensuring confidence in quality. Delivery of Dideoxy-amanitin was also prompt.

27/11/2020

— Ms. Linda Brown, Drug Development Manager (UK)

Dideoxy-amanitin’s performance was consistent across multiple studies, highlighting the reliability of BOC Sciences as a supplier.

14/12/2018

— Dr. Johannes Müller, Principal Investigator (Germany)

We appreciated the responsive support team when sourcing Dideoxy-amanitin. Their documentation simplified our internal review process.

— Dr. Matteo Ricci, Molecular Pharmacologist (Italy)

BOC Sciences provided Dideoxy-amanitin with excellent stability data, helping us evaluate long-term storage conditions effectively.

12/5/2017

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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