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Merck
CN

PZ0182

Pactamycin

≥95% (HPLC)

别名:

2-Hydroxy-6-methylbenzoic acid [(1S,2R,3R,4S,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[[(dimethylamino)carbonyl]amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentyl]methyl ester, PNU-0015800, U-15800

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关于此项目

经验公式（希尔记法）:
C28H38N4O8
化学文摘社编号:
23668-11-3
分子量:
558.62
UNSPSC Code:
51101500
PubChem Substance ID:
329823756
MDL number:
MFCD00158126

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InChI

1S/C28H38N4O8/c1-15-9-7-12-20(35)21(15)24(36)40-14-27(39)23(30-19-11-8-10-18(13-19)16(2)33)22(29)28(17(3)34,26(27,4)38)31-25(37)32(5)6/h7-13,17,22-23,30,34-35,38-39H,14,29H2,1-6H3,(H,31,37)/t17-,22-,23-,26-,27+,28-/m0/s1

SMILES string

C[C@H](O)[C@]1(NC(=O)N(C)C)[C@@H](N)[C@H](Nc2cccc(c2)C(C)=O)[C@](O)(COC(=O)c3c(C)cccc3O)[C@]1(C)O

InChI key

WVIUOSJLUCTGFK-JUJPXXQGSA-N

assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +20 to +30° in 95% ethanol

color

white to tan

solubility

DMSO: ≥12 mg/mL

storage temp.

2-8°C

Biochem/physiol Actions

Antitumor antibiotic
Pactamycin is a potent protein synthesis inhibitor, inhibiting protein synthesis at the translocation step on the 70S ribosome. It has activity against Gram-positive and Gram-negative bacteria, and broad antitumor, antiviral, and antiplasmodial activity. Cytotoxicity limits it clinical use.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

存储类别

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
081M4701V

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Hai P Nguyen et al.
Biochemistry, 58(25), 2804-2808 (2019-06-13)
Mitomycins make up a group of antitumor natural products that are biosynthesized from aminohydroxybenzoic acid (AHBA) and N-acetylglucosamine (GlcNAc). While the biosynthetic gene cluster was reported two decades ago, the mechanism by which the two building blocks, AHBA and GlcNAc
Takuya Ito et al.
Chembiochem : a European journal of chemical biology, 10(13), 2253-2265 (2009-08-12)
Pactamycin is an aminocyclopentitol-derived natural product that has potent antibacterial and antitumor activities. Sequence analysis of an 86 kb continuous region of the chromosome from Streptomyces pactum ATCC 27456 revealed a gene cluster involved in the biosynthesis of pactamycin. Gene
M Saceda et al.
The Journal of steroid biochemistry and molecular biology, 66(3), 113-120 (1998-08-27)
Previous studies suggest that post-transcriptional events play an important role in estrogen-induced loss of estrogen receptor expression. The present study shows that treatment of MCF-7 cells with estradiol resulted in a six-fold decrease in estrogen receptor mRNA half-life from 4
J Cao et al.
RNA (New York, N.Y.), 4(2), 181-188 (1998-05-07)
A 22-codon upstream open reading frame (uORF2) in the human cytomegalovirus UL4 transcript leader inhibits downstream translation in cis. Previous studies revealed that the peptide product of uORF2 mediates this inhibitory effect by interfering with translation termination at its own
S Chiaberge et al.
The Journal of biological chemistry, 273(42), 27070-27075 (1998-10-09)
AC914 mRNA, a pre-spore-specific mRNA that accumulates only in the post-aggregation stage of development, is transcribed constitutively as shown by nuclear run-off experiments and by fusing its promoter to the luciferase reporter gene. The same mRNA disappears quickly from disaggregated
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