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4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE

4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE structure

CAS No.: 606-58-6

Chemical Name:: 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE

Synonyms: e-212;e-212-1;a-399-y4;NSC 99843;NSC 63701;siromycin;uramycinb;vengicide;unamycin-b;fungamycin

CBNumber:: CB0235800

Molecular Formula:: C12H13N5O4

Molecular Weight:: 291.26

MDL Number:: MFCD00866513

MOL File:: 606-58-6.mol

MSDS File:: SDS

Last updated:2023-06-30 15:45:59

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4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Properties

Melting point	243°; mp 239-243°
alpha	D16 -45.7° (c = 1.05 in 0.1N HCl)
Boiling point	433.28°C (rough estimate)
Density	1.3067 (rough estimate)
refractive index	1.7000 (estimate)
storage temp.	2-8°C
solubility	DMSO: soluble0.90 - 1.10mg/mL, clear, colorless
form	solid
pka	12.31±0.70(Predicted)
color	White or off-white
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
FDA UNII	L7995C4D7F

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H335
Precautionary statements	P261-P305+P351+P338
WGK Germany	3
Toxicity	LD100 s.c. in mice: 10-20 mg/kg (Nishimura)

4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE price More Price(24)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	T3580	Toyocamycin ≥98% (HPLC), from Streptomyces rimosus	606-58-6	10mg	$82.8	2024-03-01	Buy
Cayman Chemical	17371	Toyocamycin ≥98%	606-58-6	1mg	$25	2021-12-16	Buy
Cayman Chemical	17371	Toyocamycin ≥98%	606-58-6	5mg	$56	2021-12-16	Buy
Cayman Chemical	17371	Toyocamycin ≥98%	606-58-6	10mg	$63	2021-12-16	Buy
Cayman Chemical	17371	Toyocamycin ≥98%	606-58-6	25mg	$125	2021-12-16	Buy

Product number	Packaging	Price	Buy
T3580	10mg	$82.8	Buy
17371	1mg	$25	Buy
17371	5mg	$56	Buy
17371	10mg	$63	Buy
17371	25mg	$125	Buy

4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Chemical Properties,Uses,Production

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

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.

Uses

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]

Uses

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.

Definition

ChEBI: 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.

Biochem/physiol Actions

Studies have implicated that toyocamycin blocks the replication of fowl plague virus.

storage

Store at +4°C

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

4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

Jaspamycin

4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Suppliers

Global( 69)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Beijing Ribio Biotech Co.,Ltd	010-62664360 +8613328773880	wucy@ribio.com.cn	China	117	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
TargetMol Chemicals Inc.	+1-781-999-5354 +1-00000000000	marketing@targetmol.com	United States	19892	58
NewCan Biotech Limited	+86-0571-86912261 +8613735419629	sales@newcanbio.com	China	10026	58
Alfa Chemistry	+1-5166625404	Info@alfa-chemistry.com	United States	21317	58
Hangzhou MolCore BioPharmatech Co.,Ltd.	+86-057181025280; +8617767106207	sales@molcore.com	China	49739	58
Nantong HI-FUTURE Biology Co., Ltd.	+undefined18051384581	sales@chemhifuture.com	China	3136	58
ZHEJIANG JIUZHOU CHEM CO., LTD	+86-0576225566889 +86-13454675544	admin@jiuzhou-chem.com；jamie@jiuzhou-chem.com；alice@jiuzhou-chem.com	China	20000	58
LEAPCHEM CO., LTD.	+86-852-30606658	market18@leapchem.com	China	43348	58
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd	+86-19164747840 +86-13119157289	13119157289@163.com	China	2971	58

Supplier	Advantage
Beijing Ribio Biotech Co.,Ltd	58
BOC Sciences	58
TargetMol Chemicals Inc.	58
NewCan Biotech Limited	58
Alfa Chemistry	58
Hangzhou MolCore BioPharmatech Co.,Ltd.	58
Nantong HI-FUTURE Biology Co., Ltd.	58
ZHEJIANG JIUZHOU CHEM CO., LTD	58
LEAPCHEM CO., LTD.	58
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd	58

4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE Spectrum

4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE(606-58-6)¹HNMR

606-58-6(4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE)Related Search:

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4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE

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NSC 63701 NSC 99843 TOYOCAMYCIN 3-d)pyrimidine-5-carbonitrile,4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo( 4-amino-5-cyano-7-(d-ribofuranosyl)-7h-pyrrolo(2,3-d)pyrimidine 4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine-5-carbonitrile a-399-y4 ahygroscopin-b antibiotic1037 antibiotica-399-y4 antibiotice212 cyanotubericidin e-212 e-212-1 naritheracin siromycin toyocamycinnucleoside unamycin-b uramycinb vengicide 7-CYANO-7-DEZXAADENOSINE 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE 4-AMINO-7-SS-D-RIBOFURANOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE Cyanotubercidin, UnaMycin B, Vengicide, E 212, 1037, E 212, Anhygroscopin B, Naritheracin 4-Aminopyrrolo[2,3-d]pyrimidine-5-carbonitrile 7-(β-D-ribofuranoside) 7-Deaza-7-cyanoadenosine Neuro 000027 4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 7H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 4-amino-7-β-D-ribofuranosyl- TOYOCAMYCIN (VENGICIDE) 4-Amino-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 4-Amino-5-cyano-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2.3-d]pyrimidine Toyacamycin RNA synthesis,CDK,mRNA cleavage,epigenetics,Toyocamycin,IRE1,CDK9 inhibitor,Cyclin dependent kinase,molecular docking,reactive oxygen species,CDKs,RNA Pol II phosphorylation,Inositol requiring enzyme 1,Fungal,Inhibitor,adenosine analog,Antibiotic,drug screening,ribosome function,inhibit,Apoptosis,extracellular signal-regulated kinases,cancer 7H-Pyrrolo[2,3-D]pyrimidine-5-carbonitrile,4-amino-7-b-d-ribofuranosyl- fungamycin 7-Cyano-7-deoxyadenosine 606-58-6 C12H13N5O4 C12H13N5O4H2O