Cephalochromin
| Code | Size | Price |
|---|
| BVT-0440-M001 | 1 mg | £160.00 |
Quantity:
| BVT-0440-M005 | 5 mg | £460.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
Cefalochromin; NSC201419; NSC627953; Antibiotic Sch45752; 2,2',3,3'-Tetrahydro-5,5',6,6',8,8'-hexahydroxy-2,2'-dimethyl-9,9'-bi[4H-naphtho[2,3-b]pyran]-4,4'-dione
Appearance:
Orange amorphous powder.
CAS:
25908-26-3
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light when in solution.
Hazards:
H302, H312, H319
InChi:
InChI=1S/C28H22O10/c1-9-4-15(30)25-19(37-9)6-12-11(5-18(33)26(34)23(12)28(25)36)21-13-7-20-24(14(29)3-10(2)38-20)27(35)22(13)17(32)8-16(21)31/h5-10,31-36H,3-4H2,1-2H3
InChiKey:
FCPNXYHPAIZMNJ-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 25908-26-3. Formula: C28H22O10. MW: 518.5. Isolated from Pseudoanguillospora sp. (strain 6577). Mycotoxin. Bis(naphtha-gamma-pyrone) derivative similar to chaetochromin and ustilaginoidin. Antibiotic. Antibacterial, antifungal and anti-algal compound. Antitumor and cytotoxic compound. Calmodulin-sensitive PDE activity inhibitor. Inhibits NO production by activated macrophages. Selective Fabl (bacterial enoyl-acyl carrier protein (ACP) reductase) inhibitor. Inducer of G0/G1 cell cycle arrest and apoptosis in human A549 cells.
Molecular Formula:
C28H22O10
Molecular Weight:
518.5
Package Type:
Plastic Vial
Precautions:
P270, P280, P301, P312, P302, P352, P312
Product Description:
Mycotoxin. Bis(naphtha-gamma-pyrone) derivative similar to chaetochromin and ustilaginoidin [1, 3]. Antibiotic [1]. Antibacterial, antifungal and anti-algal compound [1, 7]. Antitumor and cytotoxic compound [2]. Calmodulin-sensitive PDE activity inhibitor [4]. Inhibits NO production by activated macrophages [5]. Selective Fabl (bacterial enoyl-acyl carrier protein (ACP) reductase) inhibitor [6]. Inducer of G0/G1 cell cycle arrest and apoptosis in human A549 cells [8].
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
CC1CC(=O)C2=C(O)C3=C(C=C2O1)C(=CC(O)=C3O)C1=C(O)C=C(O)C2=C1C=C1OC(C)CC(=O)C1=C2O
Solubility Chemicals:
Soluble in DMSO, methanol, acetone or dichloromethane.
Source / Host:
Isolated from Pseudoanguillospora sp. (strain 6577).
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
References
Cephalochromin, dihydroiso-ustilaginoidin A and iso-ustilaginoidin A from Verticillium sp. K-113: M. Matsumoto, et al.; J. Antibiot. 28, 602 (1975) | Cytotoxicity and antitumor activities of fungal bis(naphtho-gamma-pyrone) derivatives: K. Koyama, et al.; J. Pharmacobiodyn. 11, 630 (1988) | The impairing effect of chaetochromin A and related mycotoxins on mitochondrial respiration: K. Kawai, et al.; Mycotoxins 33, 31-5 (1991) | Sch 45752, an inhibitor of calmodulin-sensitive cyclic nucleotide phosphodiesterase activity: V.R. Hedge, et al.; J. Antibiot. 46, 207 (1993) | Inhibitory effects of fungal bis(naphtho-gamma-pyrone) derivatives on nitric oxide production by a murine macrophage-like cell line, RAW 264.7, activated by lipopolysaccharide and interferon-gamma.: R. Ishii, et al.; Biol. Pharm. Bull. 28, 786 (2005) | Cephalochromin, a FabI-directed antibacterial of microbial origin: C.J. Zheng, et al.; BBRC 362, 1107 (2007) | Pseudoanguillosporin A and B: two new isochromans isolated from the edophytic fungus Pseudoanguillospora sp.: I. Kock, et al.; Eur. J. Org. Chem. 2009, 1427 (2009) | Cephalochromin induces G0/G1 cell cycle arrest and apoptosis in A549 human non-small-cell lung cancer cells by inflicting mitochondrial disruption: C.-J. Hsiao, et al.; J. Nat. Prod. 77, 758 (2014)