118292-34-5
Chemical Structure
Duocarmycin A
- CAS No.: 118292-34-5
- Formula:C26H25N3O8
- Molecular Weight:507.49
IUPAC Name: methyl (6R,7bR,8aS)-6-methyl-4,7-dioxo-2-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,4,5,6,7,8,8a-octahydrocyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate
InChIKey: AZVARJHZBXHUSO-DZQVEHCYSA-N
SMILES: O=C([C@@](N1)(C)C(C([C@@]23[C@@](C3)([H])CN(C(C(N4)=CC5=C4C(OC)=C(OC)C(OC)=C5)=O)C2=C6)=C1C6=O)=O)OC
Biological Activity: Duocarmycin A is an antitumor antibiotic and DNA alkylating agent with broad-spectrum antibacterial activity, which can serve as a payload for synthesizing antibody-drug conjugates (ADCs). Duocarmycin A selectively binds to the AT-rich minor groove of DNA, forms covalent adducts by alkylating the adenine N3 residue, thereby disrupting DNA structure and inhibiting its replication and transcription. Duocarmycin A induces apoptosis, sub-G1 phase accumulation and chromatin condensation, reduces the levels of pro-caspase-3/9, and induces p53-independent p21 expression. Duocarmycin A is widely used in the research of various malignancies, including leukemia, sarcoma, glioblastoma, as well as multiple solid tumor models such as lung cancer, breast cancer, and colorectal cancer[1][2][3].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
|
Duocarmycin A | Duocarmycin A is an antitumor antibiotic and DNA alkylating agent with broad-spectrum antibacterial activity, which can serve as a payload for synthesizing antibody-drug conjugates (ADCs). Duocarmycin A selectively binds to the AT-rich minor groove of DNA, forms covalent adducts by alkylating the adenine N3 residue, thereby disrupting DNA structure and inhibiting its replication and transcription. Duocarmycin A induces apoptosis, sub-G1 phase accumulation and chromatin condensation, reduces the levels of pro-caspase-3/9, and induces p53-independent p21 expression. Duocarmycin A is widely used in the research of various malignancies, including leukemia, sarcoma, glioblastoma, as well as multiple solid tumor models such as lung cancer, breast cancer, and colorectal cancer. | |||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
- [1]. TAKAHASHI I, et al. Duocarmycin A, a new antitumor antibiotic from Streptomyces[J]. The Journal of antibiotics, 1988, 41(12): 1915-1917.
- [2]. Morcos A, et al. A Comprehensive Review of the Antitumor Properties and Mechanistic Insights of Duocarmycin Analogs. Cancers (Basel). 2024;16(19):3293. Published 2024 Sep 27. [Content Brief]
- [3]. Hirota M, et al. Distamycin A enhances the cytotoxicity of duocarmycin A and suppresses duocarmycin A-induced apoptosis in human lung carcinoma cells. Int J Biochem Cell Biol. 2007;39(5):988-996. [Content Brief]
Keywords
