Duocarmycin B1
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| Category | Antibiotics |
| Catalog number | BBF-01772 |
| CAS | 124325-93-5 |
| Molecular Weight | 588.40 |
| Molecular Formula | C26H26BrN3O8 |
| Purity | ≥95% |
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Description
It is produced by the strain of (Pyridamycin) Streptomyces sp. DO-88. It has anti-gram-positive bacteria, gram-negative bacteria and tumor activity.
Specification
| 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 |
| InChI Key | SUWUAMDOMCWKCL-GWQKEKGPSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor) |
| Solubility | Soluble in ethanol, methanol, chloroform, DMSO |
Reference Reading
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.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
