2503-26-6 Usage
Description
Destruxin B is a cyclic depsipeptide (2503-26-6) produced by various species of fungi. It has the ability to induce apoptosis in human non-small cell lung cancer cells, display selective cytotoxic effects on human oral cancer cell lines, and inhibit hepatocellular carcinoma cell growth via modulation of the Wnt/β-catenin pathway.
Uses
Used in Pest Control Industry:
Destruxin B is used as part of destruxin-clausenamide insecticide compounds for controlling pests. Its application in this industry is due to its effectiveness in managing pest populations and reducing crop damage.
Used in Pharmaceutical Industry:
Destruxin B is studied for its selective apoptotic cell death effects on oral cancer cells treated with the compound. This application is based on its potential to target and eliminate cancer cells while minimizing damage to healthy cells, making it a promising candidate for cancer treatment research.
in vitro
the results of a previous study showed that destruxin b exhibited selective and significant time- and dose-dependent inhibitory effects on the viabilities of gnm and tscca cells but not on gf cells. these findings indicated that destruxin b was able to induce tumor specific growth inhibition in cancer cells through bax/bcl-2-mediated intrinsic mitochondrial apoptotic pathway in both time- and dose-dependent manners [1].
in vivo
animal study found that the daily subcutaneously administered destruxin b at 0.6-15 mg/kg was safe and effective in inhibiting the growth of crc cells. in addition, the expression of cleaved poly (adp-ribose) polymerase, bax, as well as active caspase-3 were observed with destruxin b treatment. moreover, the increase in tumor volumes of destruxin b treated groups were significantly lower than those of the mock-treated group [2].
References
1) Pedras et al. (2002), The destruxins: synthesis, biosynthesis, biotransformation, and biological activity; Phytochemistry, 59 579
2) Wu et al. (2013), Destruxin B Isolated from Entomopathogenic Fungus Metarhizium anisopliae Induces Apoptosis via a Bcl-2 Family-Dependent Mitochondrial Pathway in Human Nonsmall Cell Lung Cancer Cells; Evid. Based Complement. Alternat. Med,, 2013 548929
3) Liu et al. (2014), Selective apoptotic cell death effects of oral cancer cells treated with destruxin B; BMC Complement. Altern. Med., 14 207
4) Liu et al. (2014), Destruxin B inhibits hepatocellular carcinoma cell growth through modulation of the Wnt/β catenin signaling pathway and epithelial-mesenchymal transition; Toxicol. In Vitro, 28 552
Check Digit Verification of cas no
The CAS Registry Mumber 2503-26-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,0 and 3 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2503-26:
(6*2)+(5*5)+(4*0)+(3*3)+(2*2)+(1*6)=56
56 % 10 = 6
So 2503-26-6 is a valid CAS Registry Number.
InChI:InChI=1/C30H51N5O7/c1-10-19(6)24-29(40)34(9)25(18(4)5)30(41)33(8)20(7)26(37)31-14-13-23(36)42-22(16-17(2)3)28(39)35-15-11-12-21(35)27(38)32-24/h17-22,24-25H,10-16H2,1-9H3,(H,31,37)(H,32,38)/t19-,20-,21-,22-,24-,25-/m0/s1
2503-26-6Relevant articles and documents
Combinatorial Solid-Phase Synthesis and Biological Evaluation of Cyclodepsipeptide Destruxin B as a Negative Regulator for Osteoclast Morphology
Sato, Hiroshi,Yoshida, Masahito,Murase, Hayato,Nakagawa, Hiroshi,Doi, Takayuki
supporting information, p. 590 - 595 (2016/11/03)
Combinatorial synthesis and biological evaluation of cyclodepsipeptide destruxin B have been achieved. The cyclization precursors were prepared by solid-phase peptide synthesis via a split and pool method utilizing SynPhase lanterns with colored tags and cogs, followed by cleavage from the polymer-support. Macrolactonization utilizing MNBA-DMAPO in solution-phase was successfully performed in parallel to afford the desired 64-member destruxin analogues in moderate to good yields. Biological evaluation of the synthesized analogues indicated that a MeAla residue for the building block A is required to induce the desired morphological changes in osteoclast-like multinuclear cells (OCLs), and introduction of the substituent at the R4 position of a proline moiety is tolerated by the morphology and may enable the preparation of a molecular probe for the target identification in the osteoclasts.
Synthesis of the host-selective phytotoxin destruxin B. Avoiding diketopiperazine formation from an N-methyl amino acid dipeptide by use of the Boc-hydrazide derivative
Ward, Dale E.,Lazny, Ryszard,Soledade,Pedras
, p. 339 - 342 (2007/10/03)
An efficient synthesis of the cyclic hexdepsipeptide destruxin B from its component residues is described that involves a [3+3] fragment coupling followed by cyclization via the azide method. A novel feature of the synthesis is the use of the Boc-hydrozide protecting group for the C-terminal N-methylalanine residue. This group serves bath to inhibit facile diketopiperazine formation from the N-methylvalyl-N-methylalanine dipeptide and as a latent activating group for hexadepsipeptide cyclization.
