TUNICAMYCIN VII

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C39H64N4O16
Molecular Weight	844.9427
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(O[C@H]([C@H](O)[C@@H]1O)N2C=CC(=O)NC2=O)[C@H](O)C[C@H]3O[C@@H](O[C@@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4NC(C)=O)[C@H](NC(=O)\C=C\CCCCCCCCCCC(C)C)[C@@H](O)[C@H]3O

InChI

InChIKey=ZOCXUHJGZXXIGQ-NPXWYGMKSA-N

InChI=1S/C39H64N4O16/c1-20(2)14-12-10-8-6-4-5-7-9-11-13-15-25(47)41-28-32(52)29(49)23(56-38(28)59-37-27(40-21(3)45)31(51)30(50)24(19-44)57-37)18-22(46)35-33(53)34(54)36(58-35)43-17-16-26(48)42-39(43)55/h13,15-17,20,22-24,27-38,44,46,49-54H,4-12,14,18-19H2,1-3H3,(H,40,45)(H,41,47)(H,42,48,55)/b15-13+/t22-,23-,24-,27-,28-,29+,30-,31-,32-,33+,34-,35-,36-,37-,38+/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17827659
Curator's Comment: he description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28978108

Tunicamycin VII is nucleotide sugar analogs produced by several Streptomyces species. In eukaryotes, Tunicamycin VII inhibit UDP-N-acetylglucosamine-dolichol phosphate GlcNAc-1-P transferase (GPT) that catalyzes the first step in protein glycosylation. In bacteria they inhibit UDP-N-acetylmuramoyl-pentapeptide: undecaprenol phosphate MurNAc-pentapeptide-1-P transtransferase (MraY) that catalyzes an early stage in peptidoglycan cell wall assembly. Tunicamycins are substrate analog of GPT and MraY, such that the alphabeta-1'',11'-linked GlcNAc residue of the tunicamycins mimics the transferred GlcNAc-1-phosphate. Tunicamycin VII impairs ALK phosphorylation and disrupts pro-survival signaling and cell viability in various neuroblastoma cell lines. A few studies suggest that tunicamycin may work as a therapeutic drug to cancer cells as it has been shown to sensitize human colon and prostate cancer cells to TRAIL-induced apoptosis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phospho-N-acetylmuramoyl-pentapeptide-transferase 1 Target ID: CHEMBL3559642 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17827659	Inhibitor 8297
UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase 1 Target ID: Q9H3H5 Gene ID: 1798.0 Gene Symbol: DPAGT1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17827659	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28978108	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tunicamycin induced endoplasmic reticulum stress promotes apoptosis of prostate cancer cells by activating mTORC1.	2017 Sep 15	28978108

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

PC-3 cells stably expressing LC3-GFP were plated onto 2 well chamber slides (BD) and subjected to treatment with tunicamycin (10 μg/ml) for 24, 48, 72, and 96 h. Cells were fixed in 3.7% formaldehyde (Sigma), examined by confocal microscopy (Olympus FV-1000) and digital images were obtained with CCD camera of the microscope software. More than 5 puncta per cell was considered autophagy. Cells were counted under in each field and 5 different fields were scored for statistical analysis.

Name

Type

Language

TUNICAMYCIN VII

Common Name

English

TUNICAMYCIN B

Common Name

English

CORYNETOXIN U-16I

Common Name

English

TUNICAMYCIN C1

Common Name

English

Code System Code Type Description

CHEBI

64256