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| Targets |
(S)-Seco-Duocarmycin SA targets DNA, specifically binding to the minor groove. The compound induces sequence-specific alkylation of DNA, leading to irreversible DNA damage. This DNA damage inhibits DNA replication and transcription, ultimately resulting in cell death. As a DNA alkylating agent, it is a potent antitumor antibiotic with an IC50 of 10 pM.
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| ln Vitro |
In cell-free biochemical systems, (S)-Seco-Duocarmycin SA alkylates DNA, forming covalent bonds with DNA. The compound's DNA alkylation activity can be assessed using DNA binding assays, such as electrophoretic mobility shift assays (EMSA) or DNA melting temperature analysis. The compound's potent DNA alkylation activity contributes to its cytotoxic effects.
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| ln Vivo |
In cell-based assays, (S)-Seco-Duocarmycin SA exhibits potent cytotoxic activity against cancer cells. As an antitumor antibiotic with an IC50 of 10 pM, it is one of the most potent cytotoxic agents known. The compound's effects are evaluated in cancer cell lines by measuring cell viability, DNA damage, and apoptosis. It is used as an ADC cytotoxin for antibody-drug conjugates.
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| Enzyme Assay |
The cell-free assay for DNA alkylation involves incubating the compound with DNA and measuring the formation of DNA adducts. This can be assessed using mass spectrometry, radiolabeling, or HPLC analysis. The compound's DNA binding can be assessed using electrophoretic mobility shift assays (EMSA) or DNA melting temperature analysis. The compound's potent DNA alkylation activity is measured by determining the concentration required to induce DNA damage.
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| Cell Assay |
Cell-based assays for (S)-Seco-Duocarmycin SA involve culturing cancer cell lines and treating them with the compound at concentrations ranging from 0.001 to 10 nM. Cell viability is assessed using MTT or CCK-8 assays. DNA damage is assessed by measuring γ-H2AX foci or by comet assay. Apoptosis is evaluated by Annexin V staining or caspase activity assays. The compound's IC50 of 10 pM is determined from dose-response curves.
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| Animal Protocol |
In animal models, (S)-Seco-Duocarmycin SA has been evaluated as an ADC payload in tumor-bearing mice. Typical studies involve administration of the ADC to mice via intravenous routes. Tumor volumes are measured, and tissues are collected for analysis of DNA damage, apoptosis, and ADC distribution. The compound's potent cytotoxic activity contributes to the efficacy of the ADC.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (S)-Seco-Duocarmycin SA are typically evaluated as part of ADC development. As a small molecule DNA alkylating agent, it would be expected to have limited systemic exposure when administered as an ADC payload due to targeted delivery. The compound's stability and release kinetics from the ADC influence its pharmacokinetic and pharmacodynamic properties.
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| Toxicity/Toxicokinetics |
(S)-Seco-Duocarmycin SA is an extremely potent DNA alkylating agent and is expected to have significant toxicity if administered systemically. The compound is typically used as an ADC payload, where the antibody delivers the cytotoxic agent specifically to tumor cells, reducing systemic toxicity. Standard toxicity studies in animal models are conducted as part of ADC development to determine the safety profile and maximum tolerated dose.
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| References | |
| Additional Infomation |
(S)-Seco-Duocarmycin SA is a research-grade compound supplied for ADC development and cancer research. It is not an approved pharmaceutical and has no clinical trial history as a standalone compound. The compound is a DNA alkylating agent and antitumor antibiotic with an IC50 of 10 pM. It is used as an ADC payload. This product is intended for research use only.
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| Molecular Formula |
C25H24CLN3O7
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|---|---|
| Molecular Weight |
513.93
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| Exact Mass |
513.13
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| CAS # |
152785-82-5
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| Related CAS # |
Seco-Duocarmycin SA;144667-38-9
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| PubChem CID |
11005763
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
773.9±60.0 °C at 760 mmHg
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| Flash Point |
421.8±32.9 °C
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| Vapour Pressure |
0.0±2.7 mmHg at 25°C
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| Index of Refraction |
1.691
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| LogP |
1.54
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
36
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| Complexity |
836
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| Defined Atom Stereocenter Count |
1
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| SMILES |
COC1=C(C(=C2C(=C1)C=C(N2)C(=O)N3C[C@H](C4=C5C=C(NC5=C(C=C43)O)C(=O)OC)CCl)OC)OC
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| InChi Key |
SDJNZXKVYYJDDM-GFCCVEGCSA-N
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| InChi Code |
InChI=1S/C25H24ClN3O7/c1-33-18-6-11-5-14(27-20(11)23(35-3)22(18)34-2)24(31)29-10-12(9-26)19-13-7-15(25(32)36-4)28-21(13)17(30)8-16(19)29/h5-8,12,27-28,30H,9-10H2,1-4H3/t12-/m1/s1
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| Chemical Name |
methyl (8S)-8-(chloromethyl)-4-hydroxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9458 mL | 9.7290 mL | 19.4579 mL | |
| 5 mM | 0.3892 mL | 1.9458 mL | 3.8916 mL | |
| 10 mM | 0.1946 mL | 0.9729 mL | 1.9458 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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