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Duocarmycin B1

  CAS No.: 124325-93-5   Cat No.: BADC-00362   Purity: ≥95% 4.5  

It is produced by the strain of (Pyridamycin) Streptomyces sp. DO-88. It has anti-gram-positive bacteria, gram-negative bacteria and tumor activity.

Duocarmycin B1

Structure of 124325-93-5

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Category
ADC Cytotoxin
Molecular Formula
C26H26BrN3O8
Molecular Weight
588.40
Shipping
Room temperature

* 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 89B1; 1H-Pyrrolo3,2-fquinoline-2-carboxylic acid, 8-bromo-2,3,6,7,8,9-hexahydro-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl-, methyl ester, (2R,8S)-; Duocarmycin B(sub 1)
IUPAC Name
methyl (2R,8S)-8-bromo-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,7,8,9-tetrahydropyrrolo[3,2-f]quinoline-2-carboxylate
Canonical SMILES
N1(C[C@H](Cc2c3c(c(cc12)O)N[C@](C3=O)(C(=O)OC)C)Br)C(=O)c1[nH]c2c(c1)cc(c(c2OC)OC)OC
InChI
InChI=1S/C26H26BrN3O8/c1-26(25(34)38-5)23(32)18-13-8-12(27)10-30(15(13)9-16(31)20(18)29-26)24(33)14-6-11-7-17(35-2)21(36-3)22(37-4)19(11)28-14/h6-7,9,12,28-29,31H,8,10H2,1-5H3/t12-,26+/m0/s1
InChIKey
SUWUAMDOMCWKCL-GWQKEKGPSA-N
Solubility
Soluble in ethanol, methanol, chloroform, DMSO
Appearance
Yellow Powder
Shipping
Room temperature
In Vitro
Duocarmycin B1, B2, C1 and C2, from which the cyclopropane ring structure is absent. Duocarmycins were potent cytotoxic compounds to cells. The cytotoxic activity seen on Balb 3T3/H-ras cells after 72 h drug exposure was in the following order (IC50 (nM): concentration for 50% growth inhibition); SA (0.05) > A (0.3) > B2 (1.5) > B1 (3.0) > C2 (20) > C1 (40). Average minimum inhibitory concentrations (MICs) of duocarmycins against microorganisms showed essentially the same ranking order as that of cytotoxicity. There was a large difference between SA and A in their stability in aqueous solvents. For halogenated seco-compounds, a good correlation was found between their cytotoxicities in vitro and their conversion rate to duocarmycin A, suggesting that halogenated seco-compounds undergo closure to the spirocyclopropylhexadienone structure, the pertinent active form, in cells.
1. Synthesis and antitumor activity of duocarmycin derivatives: A-ring pyrrole compounds bearing beta-(5',6',7'-trimethoxy-2'-indolyl)acryloyl group
A Okamoto, S Nagamura, M Okabe, N Amishiro, E Kobayashi, H Saito, K Gomi Bioorg Med Chem . 2000 Jul;8(7):1637-43. doi: 10.1016/s0968-0896(00)00086-9.
A series of A-ring pyrrole derivatives of duocarmycin bearing beta-(5',6',7'-trimethoxy-2'-indolyl)acryloyl group were synthesized, and evaluated for in vitro anticellular activity against HeLa S3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. New Seg-B analogues bearing beta-(5',6',7'-trimethoxy-2'-indolyl)acryloyl group containing double bond as spacer had lower peripheral blood toxicity than the derivatives bearing 5',6',7'-trimethoxyindole-2'-carboxyl group in Seg-B of the natural type. Moreover, most of them exhibited potent antitumor activity against in vivo murine tumor models.
2. Synthesis and antitumor activity of water-soluble duocarmycin B1 prodrugs
A Asai, S Nagamura, E Kobayashi, H Saito, K Gomi Bioorg Med Chem Lett . 1999 Oct 18;9(20):2995-8. doi: 10.1016/s0960-894x(99)00518-1.
The water-soluble duocarmycin B1 prodrugs such as glycoside 3, phosphate 4 and carbamate 5 were synthesized for improving biological and pharmaceutical profiles of duocarmycin. Among these prodrugs, N-methylpiperazinylcarbamoyl derivative 5 exhibited potent antitumor activity against several human tumors in vivo.
3. Interconversion and stability of duocarmycins, a new family of antitumor antibiotics: correlation to their cytotoxic and antimicrobial activities in vitro
A Mihara, H Nakano, T Ogawa, I Takahashi, K Takahashi, M Ichimura Oncol Res . 1993;5(4-5):165-71.
Stability and interconversion of duocarmycins were studied in relation to their cytotoxicities and antimicrobial activities. The compounds studied included duocarmycin A and SA, which have a spirocyclopropylhexadienone moiety, and four halogenated seco-compounds of duocarmycin A: duocarmycin B1, B2, C1 and C2, from which the cyclopropane ring structure is absent. Duocarmycins were potent cytotoxic compounds to cells. The cytotoxic activity seen on Balb 3T3/H-ras cells after 72 h drug exposure was in the following order (IC50 (nM): concentration for 50% growth inhibition); SA (0.05) > A (0.3) > B2 (1.5) > B1 (3.0) > C2 (20) > C1 (40). Average minimum inhibitory concentrations (MICs) of duocarmycins against microorganisms showed essentially the same ranking order as that of cytotoxicity. There was a large difference between SA and A in their stability in aqueous solvents. For halogenated seco-compounds, a good correlation was found between their cytotoxicities in vitro and their conversion rate to duocarmycin A, suggesting that halogenated seco-compounds undergo closure to the spirocyclopropylhexadienone structure, the pertinent active form, in cells.

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

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