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Merck
CN

K1764

Sigma-Aldrich

Kazusamycin A

from Streptomyces sp., ≥95% (HPLC), aqueous methanol solution

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About This Item

Empirical Formula (Hill Notation):
C33H48O7
CAS Number:
92090-94-3
Molecular Weight:
556.73
MDL number:
MFCD03265635
UNSPSC Code:
12352200

Key Documents

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biological source

Streptomyces sp.

Assay

≥95% (HPLC)

form

aqueous methanol solution

solubility

methanol: water: soluble 7:3
DMSO: soluble
H2O: insoluble
chloroform: soluble
ethanol: soluble
hexane: insoluble
methanol: soluble

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCC(\C=C\C1OC(=O)C=CC1C)=C/C(C)C\C=C\C(C)=C\C(CO)C(=O)C(C)C(O)C(C)C\C(C)=C\C(O)=O

Biochem/physiol Actions

Kazusamycin A, an unsaturated branched chain fatty acid with a terminal lactone ring, is a hydroxy analog of Leptomycin B. It has significant in vitro cytotoxic activity against various human and mouse tumor lines encompassing a wide range of tissue types. Kazusamycin A exhibits in vivo antitumor activity against experimental murine tumors. It inhibits nuclear export and Rev translocation, a regulatory gene product in the HIV genome, at nanomolar concentrations.

Physical form

70% methanol solution.

Signal Word

Danger

Hazard Statements

H225,H301,H311,H331,H370

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

60.0 °F - closed cup

Flash Point(C)

15.56 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
035K4092

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I Umezawa et al.
Gan to kagaku ryoho. Cancer & chemotherapy, 14(3 Pt 2), 858-864 (1987-03-01)
Kazusamycins A and B and leptomycin B have a structure characteristic of an unsaturated, branched-chain fatty acid with a terminal delta-lactone ring, and show antibacterial activity on some kinds of fungi. Kazusamycin A (KZM-A) showed cytotoxic activity on mammalian cells
Ryoichi Ando et al.
Bioorganic & medicinal chemistry letters, 16(12), 3315-3318 (2006-04-18)
Novel kazusamycin A derivatives were designed in the viewpoint of decrease of reactivity at the alpha,beta-unsaturated delta-lactone moiety against Michael-type addition. Although 25-30 steps were required for the synthesis of each compound, their syntheses were achieved. Cytotoxicity against HPAC cell
I Umezawa
Gan to kagaku ryoho. Cancer & chemotherapy, 11(12 Pt 2), 2674-2680 (1984-12-01)
The antitumor antibiotic sporamycin is composed of polypeptide and non-chromophore subunits and shows remarkable antitumor activity against various animal tumors. The mechanism of action of this compound involves host-mediated antitumor activity as well as direct cytotoxic activity due to the
K Komiyama et al.
The Journal of antibiotics, 38(2), 224-229 (1985-02-01)
The antitumor activity of a new antibiotic, kazusamycin, against various murine tumors was studied by various treatment schedules. Single, intermittent, and successive injections of the antibiotic were almost equally effective against Ehrlich carcinoma, IMC carcinoma and sarcoma 180 tumor, but
K Komiyama et al.
The Journal of antibiotics, 38(2), 220-229 (1985-02-01)
The structure of a new antitumor antibiotic, kazusamycin produced by Streptomyces sp. No. 81-484, was determined on the basis of its spectral and chemical properties. Kazusamycin has a structure characteristic of an unsaturated, branched-chain fatty acid with a terminal delta-lactone
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