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Duocarmycin analog

  CAS No.:   Cat No.: BADC-00182 4.5  

Duocarmycin analog has cytotoxicity for solid tumor cells that can be used for antibody-drug conjugates (ADCs). Duocarmycins and the analogs acts via binding to the minor groove of DNA and alkylating the nucleobase adenine at the N3 position, which leads to DNA damage and cancer cell death.

Duocarmycin analog

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In Vitro
Duocarmycin analog natural products are promising anti-cancer cytotoxins but too potent for systemic use. Re-engineering of the duocarmycin scaffold has enabled the discovery of prodrugs designed for bioactivation by tissue-specific cytochrome P450 enzymes. Lead prodrugs bioactivated by both P450 isoforms CYP1A1 and CYP2W1 have shown promising results in xenograft studies.

Duocarmycin analogs are highly potent DNA minor-groove alkylating agents and promising ADC cytotoxins used as ADC payloads in antibody-drug conjugates. These compounds bind selectively to the minor groove of DNA, causing irreversible DNA alkylation, strand breaks, and apoptosis in rapidly dividing tumor cells. Their extreme cytotoxicity makes them ideal payload candidates for targeted oncology therapeutics.

Within antibody-drug conjugates, Duocarmycin analogs are conjugated to monoclonal antibodies via cleavable linkers that enable selective payload release inside tumor cells. The ADC remains stable in systemic circulation, reducing off-target toxicity, while intracellular enzymatic cleavage liberates the active cytotoxic agent. This mechanism ensures tumor-specific delivery, maximizing antitumor activity while preserving healthy tissues.

Applications of Duocarmycin analogs include their use in experimental ADCs targeting solid tumors and hematologic malignancies, such as breast cancer, lung cancer, ovarian cancer, and lymphomas. Their high potency allows therapeutic efficacy at low drug-to-antibody ratios (DARs), while chemical modifications enhance stability, linker compatibility, and conjugation efficiency. Researchers leverage Duocarmycin analogs to optimize ADC design, improve intracellular release, and achieve superior antitumor outcomes in next-generation antibody-drug conjugates.

1. A Short Review on the Synthetic Strategies of Duocarmycin Analogs that are Powerful DNA Alkylating Agents
Moses Lee, Vijay Satam, Pravin C Patil Anticancer Agents Med Chem . 2015;15(5):616-30. doi: 10.2174/1871520615666141216144116.
The duocarmycins and CC-1065 are members of a class of DNA minor groove, AT-sequence selective, and adenine-N3 alkylating agents, isolated from Streptomyces sp. that exhibit extremely potent cytotoxicity against the growth of cancer cells grown in culture. Initial synthesis and structural modification of the cyclopropa[c] pyrrolo[3,2-e]indole (CPI) DNA-alkylating motif as well as the indole non-covalent binding region in the 1980s have led to several compounds that entered clinical trials as potential anticancer drugs. However, due to significant systemic toxicity none of the analogs have passed clinical evaluation. As a result, the intensity in the design, synthesis, and development of novel analogs of the duocarmycins has continued. Accordingly, in this review, which covers a period from the 1990s through the present time, the design and synthesis of duocarmycin SA are described along with the synthesis of novel and highly cytotoxic analogs that lack the chiral center. Examples of achiral analogs of duocarmycin SA described in this review include seco-DUMSA (39 and 40), seco-amino-CBI-TMI (13, Centanamycin), and seco-hydroxy-CBI-TMI (14). In addition, another novel class of biologically active duocarmycin SA analogs that contained the seco-iso-cyclopropylfurano[2,3-e]indoline (seco-iso-CFI) and seco-cyclopropyltetrahydrofurano[2,3-f]quinoline (seco-CFQ) DNA alkylating submit was also designed and synthesized. The synthesis of seco-iso-CFI-TMI (10, Tafuramycin A) and seco-CFQ-TMI (11, Tafuramycin B) is included in this review.
2. Nitroreductase-based GDEPT
William A Denny Curr Pharm Des . 2002;8(15):1349-61. doi: 10.2174/1381612023394584.
Nitroreductases that metabolise aromatic nitro groups to hydroxylamines are attractive as enzymes for GDEPT because of the very large electronic change that this metabolism generates, providing an efficient switch that can be exploited to generate potent cytotoxins. While nitroreductase enzymes are widespread, nearly all the work using these in GDEPT has been with the nfsB gene product of Escherichia coli, an oxygen-insensitive flavin mononucleotide nitroreductase (NTR). Four classes of prodrugs for NTR have been described; dinitroaziridinylbenzamides, dinitrobenzamide mustards, 4-nitrobenzylcarbamates and nitroindolines. While some quinones are excellent substrates for NTR, none have been identified as potential GDEPT prodrugs. The most widely studied prodrug used for GDEPT in conjunction with NTR is the dinitroaziridinylbenzamide CB 1954. This shows high selectivity (>1000-fold) in cell lines transfected with NTR, has potent and long-lasting inhibition of NTR-transfected tumours in mice, and is in Phase I trial in conjunction with virally-delivered NTR enzyme. The related mustard SN 23862 has similar selectivity and superior bystander effects in animal models. Nitrobenzyl carbamates of a variety of cytotoxic amines (including aniline mustards, enediynes, duocarmycin analogues, pyrrolobenzodiazepines and the antitumour antibiotics doxorubicin, actinomycin D and mitomcyin C) are metabolised efficiently by NTR to the hydroxylamines, that fragment to release the amines. Nitroindoline derivatives of duocarmycins also show moderate selectivity for NTR-transfected cell lines in culture.
3. Duocarmycin-based antibody-drug conjugates as an emerging biotherapeutic entity for targeted cancer therapy: Pharmaceutical strategy and clinical progress
Hui Zhao, Rachel Hudson, Ming-Hai Wang, Xiang-Min Tong, Hang-Ping Yao Drug Discov Today . 2021 Aug;26(8):1857-1874. doi: 10.1016/j.drudis.2021.06.012.
Duocarmycins are a class of DNA minor-groove-binding alkylating molecules. For the past decade, various duocarmycin analogues have been used as payloads in the development of antibody-drug conjugates (ADCs). Currently, more than 15 duocarmycin-based ADCs have been studied preclinically, and some of them such as SYD985 have been granted Fast-Track Designation status. Nevertheless, progress in duocarmycin-based ADCs also faces challenges, with setbacks including the termination of BMS-936561/MDX-1203. In this review, we discuss issues associated with the efficacy, pharmacokinetic profile, and toxicological activity of these biotherapeutics. Furthermore, we summarize the latest advances in duocarmycin-based ADCs that have different target specificities and linker chemistries. Evidence from preclinical and clinical studies has indicated that duocarmycin-based ADCs are promising biotherapeutics for oncological application in the future.

What is Duocarmycin analog?

Duocarmycin analog refers to chemically modified derivatives of the natural cytotoxic Duocarmycin family. These analogs are designed for use in ADCs, retaining DNA-alkylating activity while offering improved conjugation properties and stability.

11/9/2022

Dear BOC Sciences, how is Duocarmycin analog used in ADCs?

In ADCs, Duocarmycin analogs are linked to targeting antibodies to deliver potent cytotoxic effects specifically to antigen-expressing cells. This targeted delivery enhances efficacy and reduces systemic toxicity.

5/12/2019

Could you provide guidance on which linker types suit Duocarmycin analogs?

Duocarmycin analogs are compatible with cleavable linkers, allowing controlled intracellular release, and non-cleavable linkers, which enhance circulation stability and pharmacokinetic properties of the ADC.

15/9/2021

Could you advise what handling precautions are needed for Duocarmycin analogs?

Due to their high cytotoxic potential, Duocarmycin analogs must be handled with strict laboratory safety measures, including personal protective equipment, proper containment, and adherence to regulatory guidelines during conjugation and experimental procedures.

5/11/2022

Dear BOC Sciences, what benefits do Duocarmycin analog ADCs provide?

Duocarmycin analog ADCs offer selective cell killing with reduced off-target effects, improving the therapeutic index. Their targeted delivery capability is instrumental for preclinical studies and the development of safer, more effective ADC therapies.

22/5/2022

— Dr. Peter Hall, Senior Scientist (USA)

Duocarmycin analog supplied by BOC Sciences had excellent purity and batch stability.

15/9/2021

— Prof. Isabelle Martin, Medicinal Chemistry Professor (France)

The Duocarmycin analog provided by BOC Sciences exceeded our expectations. Its exceptional purity and well-documented characterization data streamlined our cytotoxic payload development.

22/5/2022

— Dr. Thomas Weber, Medicinal Chemist (Germany)

Consistent Duocarmycin analog quality enabled smooth ADC development.

5/11/2022

— Mr. Thomas Meyer, Principal Investigator (Germany)

The Duocarmycin analog was supplied with comprehensive analytical documentation, which simplified our regulatory reporting. The compound’s strong cytotoxic activity was exactly what we needed.

11/9/2022

— Dr. Daniel Lewis, Principal Investigator (USA)

Excellent support and documentation. Duocarmycin analog facilitated our cytotoxicity assays.

— Ms. Julia Andersson, ADC Development Scientist (Sweden)

The Duocarmycin analog arrived with clear COA and MS data, which made our quality review process straightforward. Its cytotoxic strength matched the expected profile in conjugation experiments.

5/12/2019

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