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Tolytoxin

  CAS No.: 127999-44-4   Cat No.: BADC-01437 4.5  

Tolytoxin, a bioactive metabolite from cyanobacteria, is a potent antifungal antibiotic, exhibiting MICs of 0.25-8 nmol. Tolytoxin is a cyanobacterial macrolide that targets actin by inhibition of its polymerization. Tolytoxin has cytotoxic effects in cancer cells.

Tolytoxin

Structure of 127999-44-4

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Category
ADC Cytotoxin
Molecular Formula
C21H23NO6
Molecular Weight
385.410
Storage
-15°C

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

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Popular Publications Citing BOC Sciences Products
Synonyms
2,7,10-Trioxa-4-azadodecan-12-oic acid, 1-(9H-fluoren-9-yl)-3-oxo-; [2-[2-(Fmoc-Amino)ethoxy]ethoxy]acetic acid; [2-[2-[(Fmoc-amino)ethoxy]ethoxy]acetic Acid; 8-(Fmoc-amino)-3,6-dioxa-n-octanoic Acid; {2-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-ethoxy]-ethoxy}-acetic acid; Fmoc-NH-PEG2-CH2COOH; MFCD01321015; 1-(9H-Fluoren-9-yl)-3-oxo-2,7,10-trioxa-4-azadodecan-12-oic acid; [2-[2-[(9H-Fluoren-9-ylmethoxy)carbonylamino]ethoxy]ethoxy]acetic Acid; 2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]acetic acid; 8-[(9H-Fluoren-9-ylMethoxy)carbonylaMino]-3,6-dioxa-n-octanoic Acid; Fmoc-mini-PEG; Fmoc-AEEA
IUPAC Name
N-[(E,3R,4R,5R,9S,10S,11S)-10-hydroxy-11-[(1S,3S,4S,5S,7R,8S,9R,12E,14E,16S,17R,19R)-16-hydroxy-3,5,7,17-tetramethoxy-8,14-dimethyl-11-oxospiro[10,23-dioxabicyclo[17.3.1]tricosa-12,14,20-triene-4,2'-oxirane]-9-yl]-4-methoxy-3,5,9-trimethyl-6-oxododec-1-enyl]-N-methylformamide
Canonical SMILES
CC1C(CC(C2(CO2)C(CC3CC=CC(O3)CC(C(C=C(C=CC(=O)OC1C(C)C(C(C)CCC(=O)C(C)C(C(C)C=CN(C)C=O)OC)O)C)O)OC)OC)OC)OC
InChI
InChI=1S/C46H75NO13/c1-28-16-19-42(51)60-45(33(6)43(52)29(2)17-18-36(49)31(4)44(57-12)30(3)20-21-47(7)27-48)32(5)38(53-8)25-41(56-11)46(26-58-46)40(55-10)24-35-15-13-14-34(59-35)23-39(54-9)37(50)22-28/h13-14,16,19-22,27,29-35,37-41,43-45,50,52H,15,17-18,23-26H2,1-12H3/b19-16+,21-20+,28-22+/t29-,30+,31-,32-,33-,34-,35-,37-,38+,39+,40-,41-,43-,44+,45-,46-/m0/s1
InChIKey
FTGOWEQDZZMPNJ-GUMZKTDUSA-N
Density
1.3±0.1 g/cm3
Melting Point
90-92°C
Flash Point
335.6±28.7 °C
Index Of Refraction
1.580
PSA
94.09000
Vapor Pressure
0.0±1.9 mmHg at 25°C
Storage
-15°C
Boiling Point
631.4±45.0 °C at 760 mmHg
In Vivo
Tolytoxin is highly toxic to mice, exhibiting an LD50 (ip) of 1.5 mg/kg.

Tolytoxin is a macrocyclic polyether compound that functions as a highly potent ADC cytotoxin and is utilized as an ADC payload in antibody-drug conjugates. Its cytotoxic mechanism involves disruption of actin filament dynamics, leading to inhibition of cell division, cytoskeletal destabilization, and apoptosis in proliferating tumor cells. The molecular structure of Tolytoxin supports conjugation to monoclonal antibodies via cleavable or non-cleavable linkers, enabling precise intracellular delivery.

In antibody-drug conjugates, Tolytoxin is linked to antibodies through linker chemistries designed for systemic stability and selective release. The ADC remains stable in circulation, preventing premature payload activation, while intracellular enzymatic cleavage releases Tolytoxin within tumor cells. This targeted delivery ensures cytoskeletal disruption occurs selectively in tumor cells, enhancing the specificity and reproducibility of the cytotoxic effect.

Applications of Tolytoxin include its integration into ADCs targeting solid tumors and hematologic malignancies. Its chemical compatibility with various linker systems allows optimization of conjugation efficiency, intracellular release kinetics, and pharmacokinetic behavior. Tolytoxin exhibits defined cytotoxic activity in target-expressing cells and supports the development of ADCs with precise mechanism-of-action profiles, providing a mechanistically controlled approach for tumor-targeted therapy.

What is Tolytoxin?

Tolytoxin is a marine-derived cytotoxin that inhibits actin polymerization and disrupts the cytoskeleton. It is employed as a payload in ADC research for studying targeted cytotoxic effects and intracellular trafficking in cancer cell models.

29/7/2022

Dear team, how does Tolytoxin act as an ADC payload?

When conjugated to antibodies, Tolytoxin selectively enters target cells and disrupts actin dynamics, leading to cell cycle arrest and apoptosis. This mechanism allows researchers to evaluate cytoskeleton-targeting ADCs in preclinical studies.

20/3/2017

Could you kindly share what research applications Tolytoxin has?

Tolytoxin is used to study ADC delivery efficiency, intracellular cytotoxic mechanisms, and antibody-linker stability. It serves as a tool for designing and testing ADCs targeting actin-mediated cellular processes.

23/5/2022

Good afternoon! Could you please share what the chemical characteristics of Tolytoxin are?

Tolytoxin is a polyether macrolide with functional groups allowing stable conjugation to antibodies. Its structure maintains potent actin-disrupting activity after conjugation, enabling targeted ADC research.

4/4/2016

Good morning! What safety measures should be followed when handling Tolytoxin?

Tolytoxin is highly cytotoxic and requires strict lab safety measures, including PPE, fume hood use, and proper disposal procedures to ensure safe handling during ADC synthesis and experimental applications.

16/2/2016

— Dr. Peter Hall, Senior Scientist (USA)

Tolytoxin delivered by BOC Sciences had exceptional purity and stability.

23/5/2022

— Dr. Hannah White, Oncology Researcher (Canada)

Tolytoxin from BOC Sciences showed remarkable potency and stability in our early-stage studies, making it a solid candidate for further evaluation.

16/2/2016

— Mr. Patrick O’Neill, R&D Manager (Ireland)

The high-quality Tolytoxin product enabled us to generate consistent conjugates with minimal troubleshooting required.

4/4/2016

— Ms. Julia Becker, QA Specialist (Germany)

Batch records and analytical data for Tolytoxin were extremely thorough, which helped streamline our internal approval processes.

29/7/2022

— Dr. David Wilson, Principal Investigator (USA)

We appreciated the professional support provided alongside Tolytoxin. It was an excellent fit for our ADC pipeline development.

— Mr. Erik Svensson, Research Scientist (Sweden)

Tolytoxin demonstrated consistent bioactivity across our assays, and delivery timelines were always respected by BOC Sciences.

20/3/2017

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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