Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H13N5O4 |
Molecular Weight | 291.2627 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1C(=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C#N
InChI
InChIKey=XOKJUSAYZUAMGJ-WOUKDFQISA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16556935 | http://www.caymaneurope.com/pdfs/17371.pdfCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27909846
https://www.ncbi.nlm.nih.gov/pubmed/2177464
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16556935 | http://www.caymaneurope.com/pdfs/17371.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27909846
https://www.ncbi.nlm.nih.gov/pubmed/2177464
Toyocamycin is a nucleoside- type antibiotic analogue of adenosine, isolated from Streptomyces species. Toyocamycin is an antibiotic first isolated by Nishimura et al. from a new species of Streptomyces (St. toyocaensis), with a rather specific antibiotic spectrum. It strongly inhibits Candida albicans and Mycobacterium tuberculosis, without notable action on other microorganisms, such as many gram-positive and gramnegative bacteria, fungi, and yeast. Toyocamycin is an anti-tumor antibiotic with various target activities. Toyocamycin is a potent inhibitor of RNA self-cleavage in mammalian cells. It also inhibits phosphatidylinositol kinase, a cell proliferation regulator. Toyocamycin can suppress thapsigargin-, tunicamycin- and 2-deoxyglucose-induced XBP1 mRNA splicing in HeLa cells. This suppression doesn’t affect the activating of transcription factor 6 (ATF6) and PKR-like ER kinase (PERK)’s activation. Toyocamycin prevents IRE1a-induced XBP1 mRNA cleavage in vitro. In mammalian cells, toyocamycin inhibits RNA synthesis. Toyocamycin induces apoptosis of MM cells including bortezomib-resistant cells at nanomolar levels in a dose-dependent manner. It also inhibited growth of xenografts in an in vivo model of human multiple myeloma. It is also a lead compound for developing anti-MM therapy and XBP1 as an appropriate molecular target for anti-multiple myeloma therapy. Toyocamycin was the first identified small-molecule inhibitor of Rio1, showing mixed inhibition. This mode of action of toyocamycin results from its dual activity towards the Rio1 kinase. On the one hand, toyocamycin acts as an ATP-competitive inhibitor, and on the other hand, it stabilizes the less catalytically active oligomeric isoform of the Rio1 kinase.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13345725 | https://www.jstage.jst.go.jp/article/cancersci1959/56/2/56_2_219/_pdf
Curator's Comment: Toyocamycin is an antibiotic first isolated by Nishimura et al. from a new species of Streptomyces (St. toyocaens)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1163101 |
80.0 nM [IC50] | ||
Target ID: CHEMBL5975 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27909846 |
3.66 µM [IC50] | ||
Target ID: CHEMBL2096619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2177464 |
|||
Target ID: Ribozyme activity Sources: https://www.ncbi.nlm.nih.gov/pubmed/16556935 |
0.4 µM [IC50] | ||
Target ID: CHEMBL384 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2579317 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Xylotubercidin against herpes simplex virus type 2 in mice. | 1986 Nov |
|
Nucleic acid related compounds. 51. Synthesis and biological properties of sugar-modified analogues of the nucleoside antibiotics tubercidin, toyocamycin, sangivamycin, and formycin. | 1987 Mar |
|
Synthesis and evaluation of certain thiosangivamycin analogs as potential inhibitors of cell proliferation and human cytomegalovirus. | 1995 Sep 29 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22852048
Mice were treated by intraperitoneal injection of 0.5 mg/kg toyocamycin twice weekly, 1.0 mg/kg toyocamycin once weekly
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2579317
Exposure of human colon carcinoma cell line HT-29 for 24 hr to toyocamycin caused an exponential type of cell lethality resulting in a 4-log reduction of cell viability
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11824
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m10991
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134606
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99843
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300000039185
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63701
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DTXSID801031395
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L7995C4D7F
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DB13916
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606-58-6
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SUBSTANCE RECORD