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Duocarmycin A

  CAS No.: 118292-34-5   Cat No.: BADC-00223   Purity: ≥95% 4.5  

It is produced by the strain of (Pyridamycin) Streptomyces sp. DO-88. It has strong antibacterial and antitumor activity. It can inhibit gram-positive bacteria such as Staphylococcus aureus and Streptococcus faecalis (MIC is less than 0.01 μg/mL), it can also inhibit klebsiella pneumoniae (MIC is 0.032 μg/mL), other bacteria and yeast (MIC is 1-10 μg/mL).

Duocarmycin A

Structure of 118292-34-5

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Category
ADC Cytotoxin
Molecular Formula
C26H25N3O8
Molecular Weight
507.49
Target
DNA
Shipping
Room temperature
Shipping
Store at -20°C

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

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Popular Publications Citing BOC Sciences Products
Synonyms
Antibiotic DC 88A; 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; Methyl (2R,3bR,4aS)-2-methyl-3,8-dioxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,4,4a,5,6,8-octahydrocyclopropa[c]pyrrolo[3,2-e]indole-2-carboxylate; DUMA; (+)-Dunnione; (+)-duocarmycin A
IUPAC Name
methyl (1R,4R,12S)-4-methyl-3,7-dioxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),8-diene-4-carboxylate
Canonical SMILES
CC1(C(=O)C2=C(N1)C(=O)C=C3C24CC4CN3C(=O)C5=CC6=CC(=C(C(=C6N5)OC)OC)OC)C(=O)OC
InChI
InChI=1S/C26H25N3O8/c1-25(24(33)37-5)22(31)17-19(28-25)14(30)8-16-26(17)9-12(26)10-29(16)23(32)13-6-11-7-15(34-2)20(35-3)21(36-4)18(11)27-13/h6-8,12,27-28H,9-10H2,1-5H3/t12-,25-,26+/m1/s1
InChIKey
AZVARJHZBXHUSO-DZQVEHCYSA-N
Density
1.5±0.1 g/cm3
Solubility
Soluble in general organic solvents, insoluble in hexane, water
Melting Point
147-148 °C
PSA
136.26000
Appearance
Yellow Powder
Shipping
Room temperature
Storage
Store at -20°C
Boiling Point
779.8±60.0°C at 760 mmHg
In Vitro
Duocarmycin A is an antitumour antibiotic that binds covalently to the minor groove N-3 position of adenine with sequence specificity for the 3'-adenine in a d(A-A-A-A) tract in duplex DNA. The adenine ring becomes protonated on duocarmycin adduct formation resulting in charge delocalization over the purine ring system. BMS-936561 (αCD70_MED-A) is an antibody-drug conjugate composed of a fully human anti-CD70 monoclonal antibody (αCD70) conjugated with a duocarmycin derivative, MED-A, through a maleimide-containing citrulline-valine dipeptide linker.
1. Distamycin A enhances the cytotoxicity of duocarmycin A and suppresses duocarmycin A-induced apoptosis in human lung carcinoma cells
Satoru Mineshita, Hiroshi Sugiyama, Hirobumi Teraoka, Mikako Hirota, Tsuyoshi Fujiwara Int J Biochem Cell Biol . 2007;39(5):988-96. doi: 10.1016/j.biocel.2007.01.019.
Duocarmycin A (Duo), which is one of well-known antitumor antibiotics, efficiently alkylates adenine N3 at the 3' end of AT-rich sequences in the DNA. The addition of a minor groove binder, distamycin A (Dist), not only accerelates the reactivity of Duo with oligonucleotide duplex but also switches the DNA-alkylation site to guanine in GC-rich sequences. Here we examined cytotoxic effect of Duo in the coexistence of Dist using human lung carcinoma (HLC-2) cells. The cytotoxicity of Duo to HLC-2 cells was enhanced 10 times by the addition of 0.5microg/ml Dist, which was much lower than the IC(50) value of 16microg/ml. Addition of Duo alone to HLC-2 cells resulted in typically apoptotic changes, including chromatin condensation, sub-G1 accumulation in DNA histogram pattern, and decrease in procaspase-3 and 9 levels. Interestingly, these apoptotic characteristics in Duo-treated cells were suppressed by the addition of 0.5microg/ml Dist, and the G2/M population in the cell cycle progression of HLC-2 cells was largely unchanged in the coexistence of Dist along with the extremely low accumulation of p53 and higher induction of p21. In contrast, the treatment of HLC-2 cells with Dist (16microg/ml) alone was observed to induce the accumulation of p53 and cell cycle arrest at the G1 phase. These results indicate that Dist suppresses apoptosis induced by Duo as well as enhances Duo-induced cytotoxicity in living cells, and may contribute to chemotherapy for tumors resistant to inducing apoptotic cell death.
2. Concerted DNA recognition and novel site-specific alkylation by duocarmycin A with distamycin A
H Sugiyama, S Kawanishi, K Yamamoto Biochemistry . 1993 Feb 2;32(4):1059-66. doi: 10.1021/bi00055a010.
Duocarmycin A, a novel antitumor antibiotic, has a reactive cyclopropane ring, which has been reported to alkylate adenine at the 3' end of sequences of three or more consecutive A or T in DNA [Boger, D. L., et al. (1990) J. Am. Chem. Soc. 112, 8961-8971]. In order to study the DNA recognition, the reaction of DNA with duocarmycin A was performed in the presence of DNA ligands. Distamycin A, berenil, Hoechst 33258, and 4',6-diamidino-2-phenylindole (DAPI), which are minor-groove binders with affinity to A.T-rich sequences, were used. DNA-sequencing experiments showed that treatment of DNA with duocarmycin A plus distamycin A caused alkylation of guanine residues in G.C-rich sequences, which are not alkylated by duocarmycin A alone. Guanine alkylation by duocarmycin A was not observed with berenil, Hoechst 33258, or DAPI. HPLC product analysis showed that duocarmycin A reacted with a double-helical DNA octamer d(CCCCGGGG)2 in the presence of distamycin A to produce duocarmycin A-guanine adduct, while duocarmycin A alone did not react with the octamer. Chromomycin A3, which binds as a Mg(II)-coordinated dimer to G.C-rich sequences in the minor groove, inhibited the guanine alkylation by duocarmycin A in the presence of distamycin A. A footprinting experiment showed that there is a distamycin A-binding site close to the alkylated guanine residue. These results suggest that two different molecules, duocarmycin A and distamycin A, cooperatively recognize DNA sequences including consecutive G.C base pairs resulting in alkylation at the novel guanine sites. The cooperative drug recognition can be designated as "concerted DNA recognition".
3. Photoactivatable prodrugs of highly potent duocarmycin analogues for a selective cancer therapy
Lutz F Tietze, Svenia-C Duefert, Kianga Schmuck, Michael Müller, Ingrid Schuberth Chemistry . 2013 Jan 28;19(5):1726-31. doi: 10.1002/chem.201202773.
A main problem of common cancer chemotherapy is the occurrence of severe side effects caused by insufficient selectivity of the applied drugs. A possible concept to overcome this limitation is light-driven prodrug monotherapy. The synthesis as well as photochemical and biological evaluation of new photoactivatable prodrugs is described. Best results were obtained with prodrug (S,S)-7a. The photochemical labile protecting groups in (S,S)-7a can easily be removed by irradiation with UV-A light in 30 min with a power of only 2 J cm(-2). The determination of the in vitro cytotoxicity by using an HTCFA-test reveals a QIC(50) value of 8200 and the prodrug is more than two million times less cytotoxic than the corresponding seco-drug (-)-(S,S)-5 with an IC(50) value of about 110 fM. The big therapeutic window makes (S,S)-7a very suitable for its use in selective cancer therapy.

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This equation is commonly abbreviated as: C1V1 = C2V2

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Historical Records: Paclitaxel D5 | Seco-Duocarmycin MB | Ungerine Nitrate | Galantamine hydrobromide | CBT-161 | Luteolin 7-O-glucoside | Seco-DuocarmycinDMG | Duocarmycin MB | Seco-Duocarmycin MA | Duocarmycin TM | Duocarmycin A
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