606-58-6 Usage
Description
Toyocamycin (606-58-6) is an adenosine analog which inhibits ribozyme self cleavage in mammalian cells, EC50?= 0.4 μM (for expression of a luciferase reporter).1?A potent inhibitor of ER stress-induced XBP1 mRNA splicing.2?It suppresses thapsigargin-, tunicamycin- and 2-deoxyglucose-induced XBP1 mRNA splicing in HeLa cells without affecting ATF6 and PERK activation. Although unable to inhibit IRE1α phosphorylation, toyocamycin prevented IRE1α-induced XBP1 mRNA cleavage in vitro.?It inhibits not only ER stress-induced but also constitutive activation of XBP1 expression in multiple myeloma cell lines as well as in primary patient samples.2?Displays synergistic effects with bortezomib. Toyocamycin inhibits unfolded protein response and induces apoptosis in pancreatic cancer cells.3
Uses
Different sources of media describe the Uses of 606-58-6 differently. You can refer to the following data:
1. Toyocamycin is a pyrrolopyrimidine nucleoside isolated from Streptomyces toyocaensis in 1956. Toyocamycin, like other members of pyrrolopyrimidine class, is an adenosine nucleotide antimetabolite, with a broad spectrum of action against bacteria, fungi, protozoans and mammalian cell lines.
2. Toyocamycin is a natural adenosine analog first isolated from Streptomyces and shown in early studies to be cytotoxic to bacteria, fungi, and cancer cells and to have antiviral activities. Toyocamycin prevents IRE1α-induced mRNA cleavage (IC50 = 80 nM) and inhibits constitutive activation of XBP1 in multiple myeloma cell lines. It is used to study IRE1α action in the endoplasmic reticulum stress response, particularly in the context of cancer. It also inhibits phosphatidylinositol kinase in vitro (IC50 = 3.3 μg/ml), but not in cells, and blocks the ribosomal RNA-processing kinase Rio1 (IC50 = ~30 nM).[Cayman Chemical]
3. Toyocamycin Improves antibiotic production and silent gene activation in streptomyces diastatochromogenes by ribosome engineering, Preparation of tricyclic chromenone-based inhibitors of IRE-1 RNase activity.
Biochem/physiol Actions
Studies have implicated that toyocamycin blocks the replication of fowl plague virus.
References
1) Yen?et al. (2006),?Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries; RNA,?12?797
2) Ri?et al.?(2012),?Identification of Toyocamycin, an agent cytotoxic for multiple myeloma cells, as a potent inhibitor of ER stress-induced XBP1 mRNA splicing; Blood Cancer J.,?2?e79
3) Chien?et al.?(2014),?Selective inhibition of unfolded protein response induces apoptosis in pancreatic cancer cells; Oncotarget,?5?4881
Check Digit Verification of cas no
The CAS Registry Mumber 606-58-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 6 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 606-58:
(5*6)+(4*0)+(3*6)+(2*5)+(1*8)=66
66 % 10 = 6
So 606-58-6 is a valid CAS Registry Number.
InChI:InChI=1/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
606-58-6Relevant articles and documents
New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms
Spurr, Sophie S.,Bayle, Elliott D.,Yu, Wenyu,Li, Fengling,Tempel, Wolfram,Vedadi, Masoud,Schapira, Matthieu,Fish, Paul V.
supporting information, p. 4518 - 4522 (2016/08/24)
A number of new nucleoside derivatives are disclosed as inhibitors of DOT1L activity. SARs established that DOT1L inhibition could be achieved through incorporation of polar groups and small heterocycles at the 5-position (5, 6, 12) or by the application of alternative nitrogenous bases (18). Based on these results, CN-SAH (19) was identified as a potent and selective inhibitor of DOT1L activity where the polar 5-nitrile group was shown by crystallography to bind in the hydrophobic pocket of DOT1L. In addition, we show that a polar nitrile group can be used as a non-traditional replacement for heavy halogen atoms.
Phosphazole compounds
-
, (2008/06/13)
A class of substituted and unsubstituted nucleo-base analogs and related azoles, designated as "phosphazoles," is disclosed, certain preferred embodiments having the basic structure of STR1 Also disclosed are methods of making and using the new compounds.
A SYNTHESIS AND AN X-RAY ANALYSIS OF 2'-C-, 3'-C- AND 5'-C-METHYLSANGIVAMYCINS
Murai, Yasushi,Shiroto, Hironori,Ishizaki, Tatsuya,Iimori, Takamasa,Kodama, Yoshio,et al.
, p. 391 - 404 (2007/10/02)
3'-C-, 5'(R)-C- and 5'(S)-C-Methylsangivamycins (3-5) were synthesized by the trimethylsilyl triflate mediated coupling reaction of the methyl substituted ribose derivatives (7), (9) and (10) with the base moiety (11) and the successive functional group m
