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PZ0182

Pactamycin

≥95% (HPLC)

Synonym(s):

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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About This Item

Empirical Formula (Hill Notation):
C28H38N4O8
CAS Number:
23668-11-3
Molecular Weight:
558.62
UNSPSC Code:
51101500
PubChem Substance ID:
329823756
MDL number:
MFCD00158126
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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

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

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

InChI key

WVIUOSJLUCTGFK-JUJPXXQGSA-N

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

Storage Class

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
081M4701V

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Total synthesis of pactamycin.
Stephen Hanessian et al.
Angewandte Chemie (International ed. in English), 50(15), 3497-3500 (2011-03-04)
George Dinos et al.
Molecular cell, 13(1), 113-124 (2004-01-21)
The crystal structures of the universal translation-initiation inhibitors edeine and pactamycin bound to ribosomal 30S subunit have revealed that edeine induces base pairing of G693:C795, residues that constitute the pactamycin binding site. Here, we show that base pair formation by
Hwei L Ong et al.
Pflugers Archiv : European journal of physiology, 453(6), 797-808 (2006-12-16)
Store-operated Ca(2+) entry (SOCE) is activated in response to depletion of intracellular Ca(2+) from the endoplasmic reticulum (ER). A variety of agonists stimulate SOCE via IP(3)-dependent Ca(2+) depletion. SOCE is also activated by thapsigargin, an inhibitor of Ca(2+) reuptake into
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