Cylindramide | CAS:147362-39-8 | Manufacturer ChemFaces

Cylindramide

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Description:

Cylindramide is cytotoxic against B16 melanoma cells with an IC50 of 0.8 ug/m, it shows promising antiproliferative activity against several tumour cell lines. (+)-Cylindramide has anti-microbial properties.

Targets:

Antifection

In vitro:

Tetrahedron Lett., 1993, 34(6):1065-8.

Cylindramide: Cytotoxic tetramic acid lactam from the marine sponge Halichondria cylindrata Tanita & Hoshino[Reference: WebLink]

METHODS AND RESULTS:
A cytotoxic tetramic acid lactam named Cylindramide (1) has been isolated from the marine sponge Halichondria cylindrata. The structure was determined by interpretation of 2D NMR spectra as a macrocyclic lactam including an acyltetramic acid and a trisubstituted bicyclo[3. 3. 0]octene.
CONCLUSIONS:
This lactam was cytotoxic against B16 melanoma cells with an IC50 of 0.8 μg/mL.

Cylindramide Description

Source:	From Halichondria cylindrata.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

Chembiochem. 2008 Oct 13;9(15):2474-86.

Synthesis and biological properties of cylindramide derivatives: evidence for calcium-dependent cytotoxicity of tetramic acid lactams.[Pubmed: 18798209]

METHODS AND RESULTS:
To gain insight into the biological properties of tetramic acid lactam Cylindramide 1, the analogues 4 a-d bearing a cyclopentane ring instead of the pentalene unit were prepared by tandem conjugate addition/enolate trapping of cyclopentenone 10; a Sonogashira or Stille coupling, followed by a Julia-Kocienski olefination, macrolactamisation and Lacey-Dieckmann cyclisation were the key steps. The previous NMR structure of Cylindramide 1, which was based on NOE and J coupling restraints, could be refined by including residual dipolar coupling data measured for a sample of Cylindramide that was aligned in polyacrylonitrile (18 %). Biological screening of Cylindramide 1 and its analogues 2-epi-1, 20 and 4 revealed promising antiproliferative activity against several tumour cell lines. It turned out that the activity is strongly correlated to the functionalised pentalene system.
CONCLUSIONS:
The configuration of the cyclopentane ring and an intact tetramic acid lactam with the correct configuration seem to play an equal role in the cytotoxicity. The antiproliferative activity was found to be calcium dependent. Phenotypic characterisation of the mode of action showed vacuolisation and vesicle formation in the endoplasmic reticulum.

Chemistry. 2006 Mar 8;12(9):2488-503.

Total synthesis and NMR investigations of cylindramide.[Pubmed: 16389623]

METHODS AND RESULTS:
Cylindramide (1) was built up from three components: a hydroxyornithine derivative 7, a tetrazolylsulfone 8, and a substituted pentalene subunit 9. Derivative 7 was prepared in a six-step reaction sequence involving the Wittig reaction and a Sharpless asymmetric dihydroxylation starting from N-Boc-3-aminopropanal (12).
CONCLUSIONS:
As indicated by extensive 1H and 13C NMR spectroscopic investigations (DQF-COSY, ROESY spectra), the stereochemistry of synthetic Cylindramide (1) corresponds with that of the naturally occurring product. ROE data were used for molecular modeling of the lowest-energy structures for Cylindramide.

Product Name	Cylindramide
Price:
CAS No.:	147362-39-8
Catalog No.:	CFN00112
Molecular Formula:	C₂₇H₃₄N₂O₅
Molecular Weight:	466.57 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	From Halichondria cylindrata.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Anticancer Compound Library Cytotoxic Compound Library Antimicrobial Compound Library Alkaloids Compound Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.1433 mL	10.7165 mL	21.433 mL	42.866 mL	53.5825 mL
5 mM	0.4287 mL	2.1433 mL	4.2866 mL	8.5732 mL	10.7165 mL
10 mM	0.2143 mL	1.0717 mL	2.1433 mL	4.2866 mL	5.3583 mL
50 mM	0.0429 mL	0.2143 mL	0.4287 mL	0.8573 mL	1.0717 mL
100 mM	0.0214 mL	0.1072 mL	0.2143 mL	0.4287 mL	0.5358 mL

CFN00090	Panamycin 607	100905-89-3	607.86	C₃₅H₆₁NO₇
CFN00101	Aburatubolactam A	170894-24-3	508.66	C₃₀H₄₀N₂O₅
CFN00103	Altamycin A	60202-22-4	561.67	C₃₀H₄₃NO₉
CFN00112	Cylindramide	147362-39-8	466.57	C₂₇H₃₄N₂O₅
CFN00114	Discodermide	134458-00-7	482.58	C₂₇H₃₄N₂O₆
CFN00126	Antibiotic BU 2313A	69774-86-3	517.57	C₂₇H₃₅NO₉
CFN00144	Xanthobaccin A	227596-81-8	510.63	C₂₉H₃₈N₂O₆