webinar
Oct. 27-28, 2025, Boston, MA, USA - Booth 114.
Read More

Duocarmycin TM

  CAS No.: 157922-77-5   Cat No.: BADC-00605 4.5  

Duocarmycin TM is an exceptionally potent antitumor antibiotic. Duocarmycin TM is a DNA alkylator.

Duocarmycin TM

Structure of 157922-77-5

Quality
Assurance

Worldwide
Delivery

24/7 Customer
Support
Category
ADC Cytotoxin
Molecular Formula
C25H23ClN2O5
Molecular Weight
466.91
Target
DNA
Shipping
Room temperature, or blue ice upon request.

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

Size Price Stock Quantity
-- $-- In stock

Looking for different specifications? Click to request a custom quote!

Capabilities & Facilities

Popular Publications Citing BOC Sciences Products
Synonyms
[(1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydrobenzo[e]indol-3-yl]-(5,6,7-trimethoxy-1H-indol-2-yl)methanone
IUPAC Name
[(1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydrobenzo[e]indol-3-yl]-(5,6,7-trimethoxy-1H-indol-2-yl)methanone
Canonical SMILES
COC1=C(C(=C2C(=C1)C=C(N2)C(=O)N3CC(C4=C3C=C(C5=CC=CC=C54)O)CCl)OC)OC
InChI
InChI=1S/C25H23ClN2O5/c1-31-20-9-13-8-17(27-22(13)24(33-3)23(20)32-2)25(30)28-12-14(11-26)21-16-7-5-4-6-15(16)19(29)10-18(21)28/h4-10,14,27,29H,11-12H2,1-3H3/t14-/m1/s1
InChIKey
NRHDGIYFJJUFKN-CQSZACIVSA-N
Shipping
Room temperature, or blue ice upon request.
1.A novel achiral seco-amino-cyclopropylindoline (CI) analog of CC-1065 and the duocarmycins: design, synthesis and biological studies.
Toth JL, Trzupek JD, Flores LV, Kiakos K, Hartley JA, Pennington WT, Lee M
The design, synthesis and DNA binding properties of a novel achiral and amino-containing seco-cyclopropylindoline analog (seco-amino-CI-TMI, 1) of the duocarmycins are described. Thermal induced DNA cleavage studies on pUC18 DNA revealed compound 1 to preferentially bind in the minor groove and to covalently react with AT-rich sequences, particularly at the underlined adenine-N3 group of 5'-AAAAA(865)-3'. This sequence specificity is similar to adozelesin and CC-1065. Using a 4-day continuous exposure, compound 1 inhibited the growth of K562 human chronic myeloid leukemia cells in culture. Compound 1 has appreciable cytotoxicity (IC50 value of 1.30 microM) relative to compound 2 (0.15 microM), the corresponding racemic and hydroxy-seco-CI-TMI analog. These results indicate that the aminophenethyl chloride group present in compound 1 has similar sequence specific and cytotoxic properties to the hydroxy-containing seco-precursors of CC-1065 and the duocarmycins. Moreover, the results suggest that the chiral center present in the natural products is not absolutely necessary for biological activity. The novel aminophenethyl halide moiety is, therefore, a useful template from which to develop future achiral analogs of CC-1065 and the duocarmycins.
2.A novel class of achiral seco-analogs of CC-1065 and the duocarmycins: design, synthesis, DNA binding, and anticancer properties
Kupchinsky S, Centioni S, Howard T, Trzupek J, Roller S, Carnahan V, Townes H, Purnell B, Price C, Handl H, Summerville K, Johnson K, Toth J, Hudson S, Kiakos K, Hartley JA, Lee M
The synthesis, DNA binding properties, and in vitro and in vivo anticancer activity of fifteen achiral seco-cyclopropylindoline (or achiral seco-CI) analogs (5a-o) of CC-1065 and the duocarmycins are described. The achiral seco-CI analogs contain a 4-hydroxyphenethyl halide moiety that is attached to a wide range of indole, benzimidazole, pyrrole, and pyridyl-containing noncovalent binding components. The 4-hydroxyphenethyl halide moiety represents the simplest mimic of the seco-cyclopropylpyrroloindoline (seco-CPI) pharmacophore found in the natural products, and it lacks a chiral center. The sequence and minor groove specificity of the achiral compounds was ascertained using a Taq DNA polymerase stop assay and a thermal induced DNA cleavage experiment using either a fragment of pBR322 or pUC18 plasmid DNA. For example, seco-CI-InBf (5a) and seco-CI-TMI (5c) demonstrated specificity for AT-rich sequences, particularly by reacting with the underlined adenine-N3 position of 5'-AAAAA(865)-3'. This is also the sequence that CC-1065 and adozelesin prefer to alkylate. The achiral seco-CI compounds were subjected to cytotoxicity studies against several human (K562, LS174T, PC3, and MCF-7) and murine cancer cell lines (L1210 and P815). Following continuous drug exposure, the achiral compounds were found to be cytotoxic, with IC(50) values in the muM range. Interestingly, the carbamate protected compound 5p was significantly less cytotoxic than agent 5c, supporting the hypothesis that loss of HCl and formation of a spiro[2,5]cyclopropylcyclohexadienone intermediate is necessary for biological activity. The achiral seco-CI compounds 5a and 5c were submitted to the National Cancer Institute for further cytotoxicity screening against a panel of 60 different human cancer cell lines. Both compounds showed significant activity, particularly against several solid tumor cell lines. Flow cytometry studies of P815 cells that were incubated with compound 5c at its IC(50) concentration for 24h showed induction of apoptosis in a large percentage of cells. Compounds 5a and 5c were selected by the NCI for an in vivo anticancer hollow-fiber test, and received composite scores of 18 and 22, respectively. These two compounds were subsequently evaluated for in vivo anticancer activity against the growth of a human advanced stage SC UACC-257 melanoma in skid mice. At a dose of 134 mg/kg administered IP, compound 5c gave a T/C value of 40% (for day 51), and the median number of days of doubling tumor growth was 27.7, versus 15.8 for untreated animals. For compound 5a, at 200mg/kg, the T/C was 58% and the median number of days of doubling tumor growth was 20.0 versus 8.7 for untreated animals. At these doses no toxicity or weight loss was observed for either compound. Furthermore, compound 5c was not toxic to murine bone marrow cell growth in culture, at a dose that was toxic for the previously reported seco-CBI (cyclopropylbenzoindoline)-TMI (4).
3.A novel class of in vivo active anticancer agents: achiral seco-amino- and seco-hydroxycyclopropylbenz[e]indolone (seco-CBI) analogues of the duocarmycins and CC-1065.
Sato A, McNulty L, Cox K, Kim S, Scott A, Daniell K, Summerville K, Price C, Hudson S, Kiakos K, Hartley JA, Asao T, Lee M.
One achiral seco-hydroxycyclopropylbenz[e]indolone (seco-CBI) (12) and seven achiral seco-amino-CBI (11a-g) analogues of CC-1065 and the duocarmycins were designed, synthesized and evaluated for their DNA-binding and anticancer properties. These compounds contain a core 2-chloroethylnaphthalene structure and they do not have a stereocenter. From thermal cleavage gel analyses, compounds 11a-g and 12 demonstrated similar covalent sequence specificity to adozelesin 3 and the racemic seco-CBI-TMI 4 for binding to the 5'-AAAAA(865)-3' site. Continuous exposure of human (K562) and murine (B16, L1210 and P815) cancer cell lines to the compounds demonstrated their significant cytotoxicity, with IC50 values in the sub-micromolar range. Generally, a good leaving group on the ethyl moiety and a free amino or hydroxyl group on the naphthyl moiety are essential for activity. According to NCI's cytotoxicity screen, compounds 11a and 12 were active against human cancer cell lines derived from lung, colon, melanoma, renal system, and breast. At the respective doses of 15 and 20 mg/kg (administered via an ip route), compounds 11a and 12 inhibited the growth of murine B16-F0 melanoma in C57BL/6 mice, with minimal toxicity, and 11a gave a significant anticancer effect. The in vivo anticancer activity of compound 11a was confirmed in a human tumor xenograft study (advanced stage SC-OVCAR-3 ovarian cancer growing in scid mice). Finally, compound 11a was not toxic to murine bone marrow cell growth in culture at a dose that was toxic for the previously reported compound 4.

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

Related Products

Contact our experts today for pricing and comprehensive details on our ADC offerings.

You May Also Be Interested In

From cytotoxin synthesis to linker design, discover our specialized services that complement your ADC projects.

ADC Payload Development Biological Payload Chemical Payload Protein Toxin Nanocarrier Microtubule Inhibitors DNA Damaging Agents RNA Polymerase Inhibitors Protein Degraders

Unlock Deeper ADC Insights

Learn more about payload design, linker strategies, and integrated CDMO support through our curated ADC content.

Maytansine and Its Analogues Cytotoxic Agents Used in Antibody–Drug Conjugates Exatecan Mesylate in ADCs: A New Topo I Inhibitor What is Calicheamicin? What is Monomethyl Auristatin E (MMAE)? What is Monomethyl Auristatin F (MMAF)? What is Pyrrolobenzodiazepine (PBD)? Antiviral Potential of Thapsigargin in COVID-19 Research ADC Payloads Explained: Current Types and Cutting-Edge Research Progress Tubulin Inhibitors - Highly Potential ADC Payloads

Explore More ADC Products

Find exactly what your project needs from our expanded range of ADCs, offering flexible options to fit your timelines and goals.

ADC Cytotoxin

Powerful Targeted Cancer Solutions

ADC  Cytotoxin with Linker

Enhanced Stability And Efficacy

ADC Linker

Precise Conjugation For Success

Antibody-Drug  Conjugates (ADCs)

Maximized Therapeutic Performance

Auristatins

Next-Level Tubulin Inhibition

Calicheamicins

High-Impact DNA Targeting

Camptothecins

Advanced Topoisomerase Inhibition

Daunorubicins / Doxorubicins

Trusted Anthracycline Payloads

Duocarmycins

Potent DNA Alkylation Agents

Maytansinoids

Superior Microtubule Disruption

Pyrrolobenzodiazepines

Ultra-Potent DNA Crosslinkers

Traditional Cytotoxic Agents

Proven Chemotherapy Solutions

Cleavable Linker

Precise Intracellular Drug Release

Non-Cleavable Linker

Exceptional Long-Term Stability

Historical Records: Telomestatin | Paclitaxel D5 | Seco-Duocarmycin MB | Ungerine Nitrate | Galantamine hydrobromide | CBT-161 | Luteolin 7-O-glucoside | Seco-DuocarmycinDMG | Duocarmycin MB | Seco-Duocarmycin MA | Duocarmycin TM
Send Inquiry
Verification code
Inquiry Basket