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Purity: ≥98%
Toyocamycin (also known as Vengicide) is a derivative of adenosine isolated from Streptomyces toyocaensis. Toyocamycin blocks RNA synthesis and ribosome function.
| ln Vitro |
Inhibiting both IRE1α-XBP1 buffer activation caused below the endoplasmic reticulum and XBP1 mRNA splicing elicited above it, toyocamycin (0-0.3 μM; 4 h) blocks both processes concurrently [1]. In MM cell lines, constitutive activation of XBP1 is inhibited by toyocamycin (0-0.3 μM; 24 h) and toyocamycin (250 nM; 48 h) [1]. Toyocamycin (50 μM–0.05 nM; 48 and 72 hours). Toyocamycin (0-100 nM; 24 or 48 hours) did not immediately cause cytotoxicity against YB5 and HCT116 with cell survival above 50%; nevertheless, when treated with 10 nM for 24 hours, cancer cells are eradicated two weeks later [2]. By blocking p38 on ERK MAPK, toyocamycin (60 nM; 0-48 h) inhibits ROS-mediated cell fluorescence and enhances p38/ERK MAPK activation [3].
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| ln Vivo |
Fungamycin (0.5 mg/kg, 1.0 mg/kg; intraperitoneally; twice weekly; 2 weeks) exhibits anticancer activity in a human multiple myeloma (MM) xenograft model. Bortezomib This antitumor activity can be increased in
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| Cell Assay |
Western Blot analysis [1]
Cell Types: HeLa, HEK293 Tested Concentrations: 0, 0.03, 0.1, 0.3 μM Incubation Duration: 4 hrs (hours) Experimental Results: Neither inhibited tunicamycin-induced ATF6 nor PERK activation. Inhibited IRE1α-induced XBP1 mRNA cleavage without affecting phosphorylation on IRE1α Ser724. Western Blot Analysis[3] Cell Types: Human prostate cancer PC-3 cells Tested Concentrations: 60 nM Incubation Duration: 12, 24, 36, 48 hrs (hours) Experimental Results: Inhibited the phosphorylation level of AKA, while reducing the phosphorylation level of ERK and p38. Cell viability assay[3] Cell Types: PC-3 and RWPE-1 Cell Tested Concentrations: 0, 20, 40, 60, 80, 100 nM Incubation Duration: 24 or 48 hrs (hours) Experimental Results: Inhibited cell viability and induced apoptosis by 62%. |
| Animal Protocol |
Animal/Disease Models: SCID (severe combined immunodeficient) mouse are injected with human multiple myeloma (MM) cells [1].
Doses: 0.5 mg/kg, 1.0 mg/kg. Route of Administration: intraperitoneal (ip) injection; tumor activity [1]. Twice a week; 2-week Experimental Results: Tumor volume Dramatically diminished. Compared with bortezomib, the antitumor activity is enhanced, manifested by smaller tumor size. |
| References |
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| Additional Infomation |
Toyocamycin is an N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group. It has a role as an antimetabolite, an antineoplastic agent, a bacterial metabolite and an apoptosis inducer. It is a N-glycosylpyrrolopyrimidine, a nitrile, a ribonucleoside and an antibiotic antifungal agent.
4-Amino-5-cyano-7-(D-ribofuranosyl)-7H- pyrrolo(2,3-d)pyrimidine. Antibiotic antimetabolite isolated from Streptomyces toyocaensis cultures. It is an analog of adenosine, blocks RNA synthesis and ribosome function, and is used mainly as a tool in biochemistry. Toyocamycin has been reported in Streptomyces toyocaensis, Streptomyces diastatochromogenes, and other organisms with data available. 4-Amino-5-cyano-7-(D-ribofuranosyl)-7H- pyrrolo(2,3-d)pyrimidine. Antibiotic antimetabolite isolated from Streptomyces toyocaensis cultures. It is an analog of adenosine, blocks RNA synthesis and ribosome function, and is used mainly as a tool in biochemistry. |
| Molecular Formula |
C12H13N5O4
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|---|---|
| Molecular Weight |
291.26272
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| Exact Mass |
291.097
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| CAS # |
606-58-6
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| PubChem CID |
11824
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| Appearance |
White to off-white solid powder
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| Density |
1.91g/cm3
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| Boiling Point |
721.1ºC at 760 mmHg
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| Flash Point |
389.9ºC
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| Index of Refraction |
1.849
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| LogP |
-1.6
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
21
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| Complexity |
443
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1=C(C2=C(N=CN=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C#N
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| InChi Key |
XOKJUSAYZUAMGJ-WOUKDFQISA-N
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| InChi Code |
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
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| Chemical Name |
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~343.34 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4334 mL | 17.1668 mL | 34.3336 mL | |
| 5 mM | 0.6867 mL | 3.4334 mL | 6.8667 mL | |
| 10 mM | 0.3433 mL | 1.7167 mL | 3.4334 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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