Toyocamycin
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| Category | Antibiotics |
| Catalog number | BBF-03421 |
| CAS | 606-58-6 |
| Molecular Weight | 291.26 |
| Molecular Formula | C12H13N5O4 |
| Purity | >95% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-03421 | 100 mg | $499 | In stock |
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Add to cartDescription
Toyocamycin is a pyrrolopyrimidine nucleoside isolated from streptomyces toyocaensis, and also an adenosine nucleotide antimetabolite. It has a broad spectrum of action against bacteria, fungi, protozoans and mammalian cell lines.
Specification
| Synonyms | Vengicide; Siromycin; Cyanotubericidin; Ahygroscopin-B; Antibiotic 1037; Uramycin B; NSC 63701 |
| Storage | Store at-20°C |
| IUPAC Name | 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile |
| Canonical SMILES | C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)C#N |
| InChI | InChI=1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1 |
| InChI Key | XOKJUSAYZUAMGJ-WOUKDFQISA-N |
Properties
| Appearance | White to Fawn Solid |
| Application | Antimetabolites, Antineoplastic |
| Antibiotic Activity Spectrum | neoplastics (Tumor); fungi; mycobacteria |
| Boiling Point | 721.2°C at 760 mmHg |
| Melting Point | 266-286°C |
| Density | 1.9 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Substantial improvement of toyocamycin production in Streptomyces diastatochromogenes by cumulative drug-resistance mutations
Xiao-Ping Yu, Yin Xiao, Kozo Ochi, Gu Tang, Zhen-Yan Cao, Xu-Ping Shentu PLoS One . 2018 Aug 30;13(8):e0203006. doi: 10.1371/journal.pone.0203006.
Toyocamycin is a member of the nucleoside antibiotic family and has been recognized as a promising fungicide for the control of plant diseases. However, low productivity of toyocamycin remains an important bottleneck in its industrial production. Therefore, dramatic improvements of strains for overproduction of toyocamycin are of great interest in applied microbiology research. In this study, we sequentially selected for mutations for multiple drug resistance to promote the overproduction of toyocamycin by Streptomyces diastatochromogenes 1628. The triple mutant strain, SD3145 (str str par), was obtained through sequential screenings. This strain showed an enhanced capacity to produce toyocamycin (1500 mg/L), 24-fold higher than the wild type in GYM liquid medium. This dramatic overproduction was attributed at least partially to the acquisition of an rsmG mutation and increased gene expression of toyA, which encodes a LuxR-family transcriptional regulator for toyocamycin biosynthesis. The expression of toyF and toyG, probably directly involved in toyocamycin biosynthesis, was also enhanced, contributing to toyocamycin overproduction. By addition of a small amount of scandium (ScCl3·6H2O), the mutant strain, SD3145, produced more toyocamycin (2664 mg/L) in TPM medium, which was the highest toyocamycin level produced in shake-flask fermentation by a streptomycete so far. We demonstrated that introduction of combined drug resistance mutations into S. diastatochromogenes 1628 resulted in an obvious increase in the toyocamycin production. The triple mutant strain, SD3145, generated in our study could be useful for improvement of industrial production of toyocamycin.
2. Selective CDK9 Inhibition by Natural Compound Toyocamycin in Cancer Cells
Jean-Pierre J Issa, Gennaro Calendo, Hanghang Zhang, Somnath Pandey, Andrew J Andrews, Ryan A Henry, Stephen B Baylin, Jozef Madzo, Rahinatou Djibo, Noël J-M Raynal, Anaïs Darracq, Rafael Najmanovich Cancers (Basel) . 2022 Jul 8;14(14):3340. doi: 10.3390/cancers14143340.
Aberrant transcription in cancer cells involves the silencing of tumor suppressor genes (TSGs) and activation of oncogenes. Transcriptomic changes are associated with epigenomic alterations such as DNA-hypermethylation, histone deacetylation, and chromatin condensation in promoter regions of silenced TSGs. To discover novel drugs that trigger TSG reactivation in cancer cells, we used a GFP-reporter system whose expression is silenced by promoter DNA hypermethylation and histone deacetylation. After screening a natural product drug library, we identified that toyocamycin, an adenosine-analog, induces potent GFP reactivation and loss of clonogenicity in human colon cancer cells. Connectivity-mapping analysis revealed that toyocamycin produces a pharmacological signature mimicking cyclin-dependent kinase (CDK) inhibitors. RNA-sequencing revealed that the toyocamycin transcriptomic signature resembles that of a specific CDK9 inhibitor (HH1). Specific inhibition of RNA Pol II phosphorylation level and kinase assays confirmed that toyocamycin specifically inhibits CDK9 (IC50= 79 nM) with a greater efficacy than other CDKs (IC50values between 0.67 and 15 µM). Molecular docking showed that toyocamycin efficiently binds the CDK9 catalytic site in a conformation that differs from other CDKs, explained by the binding contribution of specific amino acids within the catalytic pocket and protein backbone. Altogether, we demonstrated that toyocamycin exhibits specific CDK9 inhibition in cancer cells, highlighting its potential for cancer chemotherapy.
3. Toyocamycin specifically inhibits auxin signaling mediated by SCFTIR1 pathway
Yutaka Oono, Leroy B Townsend, Ken-ichiro Hayashi, Shuichi Kamio, Hiroshi Nozaki Phytochemistry . 2009 Jan;70(2):190-7. doi: 10.1016/j.phytochem.2008.12.020.
The auxins, plant hormones, play a crucial role in many aspects of plant development by regulating cell division, elongation and differentiation. Toyocamycin, a nucleoside-type antibiotic, was identified as auxin signaling inhibitor in a screen of microbial extracts for inhibition of the auxin-inducible reporter gene assay. Toyocamycin specifically inhibited auxin-responsive gene expression, but did not affect other hormone-inducible gene expression. Toyocamycin also blocked auxin-enhanced degradation of the Aux/IAA repressor modulated by the SCF(TIR1) ubiquitin-proteasome pathway without inhibiting proteolytic activity of proteasome. Furthermore, toyocamycin inhibited auxin-induced lateral root formation and epinastic growth of cotyledon in the Arabidopsis thaliana plant. This evidence suggested that toyocamycin would act on the ubiquitination process regulated by SCF(TIR1) machineries. To address the structural requirements for the specific activity of toyocamycin on auxin signaling, the structure-activity relationships of nine toyocamycin-related compounds, including sangivamycin and tubercidin, were investigated.
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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 ╳
