Alborixin

Alborixin

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Alborixin
Category Antibiotics
Catalog number BBF-00661
CAS 57760-36-8
Molecular Weight 885.17
Molecular Formula C48H84O14
Purity 95%

Online Inquiry

Description

It is produced by the strain of Streptomyces albus and Str. hygro-scowpicus. It has the function of ion carrier.

Specification

Synonyms Antibiotic S 14750A; 0I21L1W8NY; SCHEMBL2480082; CHEBI:77940; LS-16248; Q27147545; 2H-Pyran-2-acetic acid,6-[(2R,3S)-3-[(2R,5S,6R)-6-[[(2R,3S,5R,6R)-6-[(S)-[(2S,2'R,3'R,5S,5'S)-5'-[(2R,5R,6S)-6-ethyltetrahydro-5-hydroxy-5-methyl-2H-pyran-2-yl]octahydro-2'-hydroxy-2,3',5'-trimethyl[2,2'-bifuran]-5-yl]hydroxymethyl]tetrahydro-6-hydroxy-3,5-dimethyl-2H-pyran-2-yl]methyl]tetrahydro-6-hydroxy-5-methyl-2H-pyran-2-yl]-2-hydroxybutyl]tetrahydro-a,3,5-trimethyl-, (aR,2S,3S,5R,6S)-
IUPAC Name (2R)-2-[(2S,3S,5R,6S)-6-[(2R,3S)-3-[(2R,5S,6R)-6-[[(2R,3S,5R,6R)-6-[(R)-[(2S,5S)-5-[(2R,3R,5S)-5-[(2R,5R,6S)-6-ethyl-5-hydroxy-5-methyloxan-2-yl]-2-hydroxy-3,5-dimethyloxolan-2-yl]-5-methyloxolan-2-yl]-hydroxymethyl]-6-hydroxy-3,5-dimethyloxan-2-yl]methyl]-6-hydroxy-5-methyloxan-2-yl]-2-hydroxybutyl]-3,5-dimethyloxan-2-yl]propanoic acid
Canonical SMILES CCC1C(CCC(O1)C2(CC(C(O2)(C3(CCC(O3)C(C4(C(CC(C(O4)CC5(C(CCC(O5)C(C)C(CC6C(CC(C(O6)C(C)C(=O)O)C)C)O)C)O)C)C)O)O)C)O)C)C)(C)O
InChI InChI=1S/C48H84O14/c1-13-38-43(10,53)18-17-39(58-38)44(11)23-30(7)48(56,62-44)45(12)19-16-35(59-45)41(50)47(55)29(6)21-26(3)37(61-47)24-46(54)28(5)14-15-34(60-46)31(8)33(49)22-36-25(2)20-27(4)40(57-36)32(9)42(51)52/h25-41,49-50,53-56H,13-24H2,1-12H3,(H,51,52)/t25-,26+,27+,28+,29-,30-,31+,32-,33-,34-,35+,36+,37-,38+,39-,40+,41-,43-,44+,45+,46-,47-,48-/m1/s1
InChI Key WWDHGOLBPBWCNJ-GXXSWWTOSA-N

Properties

Appearance White Amorphous Powder
Boiling Point 929.8 °C at 760 mmHg
Melting Point 100-105 °C
Density 1.157 g/cm3
Solubility Soluble in Acetone, Methyl Ester

Reference Reading

1. Isolation and characterization of alborixin from Streptomyces scabrisporus: A potent cytotoxic agent against human colon (HCT-116) cancer cells
Aabid Manzoor Shah, Abubakar Wani, Parvaiz H Qazi, Shakeel-U Rehman, Saleem Mushtaq, Shiekh Abid Ali, Aehtesham Hussain, Aiyatullah Shah, Asif Khurshid Qazi, Ubaid Sharif Makhdoomi, Abid Hamid, Ajay Kumar Chem Biol Interact. 2016 Aug 25;256:198-208. doi: 10.1016/j.cbi.2016.06.032. Epub 2016 Jul 1.
The ethyl acetate extract from the fermentation broth of an actinomycete strain, identified as Streptomyces scabrisporus isolated from soil of Kashmir Himalayas - India, exhibited significant cytotoxic activity against a panel of human cancer cell lines. The active fraction subjected to column chromatography led to the isolation of pharmacologically potent anticancer compound whose structure was established to be alborixin on the basis of spectral data analysis. The compound exhibited antiproliferative activity against panel of cell lines N2a, MCF-7, MiaPaca-2, PC-3, HCT-116, MDA-MB-231, HL-60 and A-549 cells with IC50 of 9.7, 15.4, 7.2, 8.1, 3.2, 9.7, 7.5 and 11.5 μM respectively. Alborixin displayed the maximum cytotoxic activity against HCT-116 human colon carcinoma cells and therefore further studies were carried on this cell line. Alborixin decreased the clonogenic potential of HCT-116 cells in a dose dependent manner. It induced apoptotic cell death in HCT116 cells that were confirmed by Flow cytometric analysis of Annexin V/PI staining and microscopic examination of cellular morphology through DAPI-stained cells. Biochemical evidence of apoptosis came from elevating the intracellular ROS level that was accompanied by mitochondrial membrane potential loss, decreasing the expression profile of anti-apoptotic protein Bcl-2, whereas it augments cleavage of caspase-3 and PARP-1, activates caspase-8 and 9 with concomitant increase in expression of proapoptotic protein Bax in a dose dependent manner. These results indicate that alborixin obtained from Streptomyces scabrisporus IIIM55 induces apoptotic cell death in colon cancer cells HCT-116 and can be further evaluated for its potential as an anticancer agent.
2. Alborixin clears amyloid-β by inducing autophagy through PTEN-mediated inhibition of the AKT pathway
Abubakar Wani, Mehak Gupta, Masroor Ahmad, Aabid M Shah, Aitizaz Ul Ahsan, Parvaiz H Qazi, Fayaz Malik, Gurdarshan Singh, Parduman R Sharma, Amal Kaddoumi, Sandip B Bharate, Ram A Vishwakarma, Ajay Kumar Autophagy. 2019 Oct;15(10):1810-1828. doi: 10.1080/15548627.2019.1596476. Epub 2019 Apr 2.
Imbalance in production and clearance of amyloid beta (Aβ) is the primary reason for its deposition in Alzheimer disease. Macroautophagy/autophagy is one of the important mechanisms for clearance of both intracellular and extracellular Aβ. Here, through screening, we identified alborixin, an ionophore, as a potent inducer of autophagy. We found that autophagy induced by alborixin substantially cleared Aβ in microglia and primary neuronal cells. Induction of autophagy was accompanied by up regulation of autophagy proteins BECN1/Beclin 1, ATG5, ATG7 and increased lysosomal activities. Autophagy induced by alborixin was associated with inhibition of the phosphoinositide 3-kinase (PI3K)-AKT pathway. A knock down of PTEN and consistent, constitutive activation of AKT inhibited alborixin-induced autophagy and consequent clearance of Aβ. Furthermore, clearance of Aβ by alborixin led to significant reduction of Aβ-mediated cytotoxicity in primary neurons and differentiated N2a cells. Thus, our findings put forward alborixin as a potential anti-Alzheimer therapeutic lead. Abbreviations: Aβ: amyloid beta; ALB: alborixin; ATG: autophagy-related; BECN1: beclin 1; DAPI: 4, 6-diamidino-2-phenylindole; DCFH-DA: 2,7-dichlorodihydrofluorescein diacetate; fAβ: fibrillary form of amyloid beta; GFAP: glial fibrillary acidic protein; MAP1LC3B/LC3B: microtubule-associated protein 1 light chain 3 beta; MAP2: microtubule-associated protein 2; MTOR: mechanistic target of rapamycin kinase; PTEN: phosphatase and tensin homolog; ROS: reactive oxygen species; SQSTM1: sequestosome 1; TMRE: tetramethylrhodamine, ethyl ester.
3. Differential in vitro activities of ionophore compounds against Plasmodium falciparum and mammalian cells
C Gumila, M L Ancelin, G Jeminet, A M Delort, G Miquel, H J Vial Antimicrob Agents Chemother. 1996 Mar;40(3):602-8. doi: 10.1128/AAC.40.3.602.
Twenty-two ionophore compounds were screened for their antimalarial activities. They consisted of true ionophores (mobile carriers) and channel-forming quasi-ionophores with different ionic specificities. Eleven of the compounds were found to be extremely efficient inhibitors of Plasmodium falciparum growth in vitro, with 50% inhibitory concentrations of less than 10 ng/ml. Gramicidin D was the most active compound tested, with 50% inhibitory concentration of 0.035 ng/ml. Compounds with identical ionic specificities generally had similar levels of antimalarial activity, and ionophores specific to monovalent cations were the most active. Compounds were further tested to determine their in vitro toxicities against mammalian lymphoblast and macrophage cell lines. Nine of the 22 compounds, i.e., alborixin, lonomycin, nigericin, narasin, monensin and its methylated derivative, lasalocid and its bromo derivative, and gramicidin D, most specific to monovalent cations, were at least 35-fold more active in vitro against P. falciparum than against the two other mammalian cell lines. The enhanced ability to penetrate the erythrocyte membrane after infection could be a factor that determines ionophore selectivity for infected erythrocytes.

Recommended Products

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* 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
g/mol
g

Recently viewed products

Online Inquiry

Verification code
cartIcon
Inquiry Basket