Ansamitocin PDM-3
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| Category | Bioactive by-products |
| Catalog number | BBF-05710 |
| CAS | 77353-69-6 |
| Molecular Weight | 621.1 |
| Molecular Formula | C31H41ClN2O9 |
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Description
Ansamitocin PDM-3 is an ansamycin antibiotic isolated from Actinosynnema pretiosum, and exhibits antitumor activity.
Specification
| Synonyms | Ansamitocin P-3; N-Demethylansamitocin P 3; N-Demethylansamitocin P-3 |
| IUPAC Name | [(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-methylpropanoate |
| Canonical SMILES | CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)NC(=O)CC(C4(C1O4)C)OC(=O)C(C)C)C)OC)(NC(=O)O2)O |
| InChI | InChI=1S/C31H41ClN2O9/c1-16(2)28(36)42-24-14-25(35)33-20-12-19(13-21(39-6)26(20)32)11-17(3)9-8-10-23(40-7)31(38)15-22(41-29(37)34-31)18(4)27-30(24,5)43-27/h8-10,12-13,16,18,22-24,27,38H,11,14-15H2,1-7H3,(H,33,35)(H,34,37)/b10-8+,17-9+/t18-,22+,23-,24+,27+,30+,31+/m1/s1 |
| InChI Key | BOYNDXJJKZMFBK-PRWXLFGZSA-N |
Properties
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 833.1±65.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. A fluorescent probe and a photoaffinity labeling reagent to study the binding site of maytansine and rhizoxin on tubulin
T Sawada, Y Kato, H Kobayashi, Y Hashimoto, T Watanabe, Y Sugiyama, S Iwasaki Bioconjug Chem. 1993 Jul-Aug;4(4):284-9. doi: 10.1021/bc00022a006.
A fluorescent probe (20-demethoxy-20-[3-[[[5-(dimethylamino)naphthalen-1-yl]sulfonyl] amino]propyl]maytansinol 3-isobutyrate, Dan-PDM-3) and a photoaffinity labeling reagent (20-demethoxy-20-[(p-azidobenzoyl)oxy]maytansinol 3-isobutyrate, DABMI) were prepared by derivatization of ansamitocin P-3 (ASMP-3), a maytansinoid. Dan-PDM-3 consists of a tethered dansyl moiety and a maytansinoid moiety. DABMI contains a p-azidobenzoyl group instead of the tethered dansyl moiety of Dan-PDM-3. These compounds were synthesized by reacting 20-demethoxy-20-hydroxymaytansinol-3 isobutyrate (PDM-3) with the corresponding alkyl halide or benzoic acid. Both inhibit tubulin polymerization as potently as ASMP-3 and compete with ASMP-3 for binding to tubulin. The inhibition constants (Ki) of DABMI for the binding to tubulin of rhizoxin and ASMP-3 were 0.54 and 0.36 microM, respectively, which were nearly equal to the dissociation constant (Kd = 0.43 microM) of DABMI measured by the use of [14C]DABMI. The results suggest that Dan-PDM-3 and DABMI interacted with tubulin at the same site as rhizoxin and maytansine. DABMI is irreversibly bound to tubulin upon irradiation. Dan-PDM-3 and DABMI should be useful probes for studying the binding site.
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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 ╳
