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ALX-380-058
Revised 03-Apr-08
Citrinin
SYNONYMS
Antimycin
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antibiotics Other Products
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
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ALX-380-058-M001
1 mg
15.00 USD
ALX-380-058-M005
5 mg
60.00 USD
ALX-380-058-M010
10 mg
105.00 USD
ALX-380-058-M025
25 mg
210.00 USD
Product Specification
FORMULA:
C
13
H
14
O
5
MW:
250.3
CAS NUMBER:
518-75-2
MERCK INDEX:
14:
2327
SOURCE/HOST:
Isolated from
Penicillium citrinum
.
PURITY:
≥98%
APPEARANCE:
Yellow crystals.
SOLUBILITY:
Soluble in 100% ethanol or dioxane. Insoluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
+4°C
USE/STABILITY:
Solutions change color with changes in pH from yellow (pH 4.6) to red (pH 9.9).
HAZARD:
TOXIC.
Product Description
Antibiotic. Induces mitochondrial permeability pore opening and inhibits respiration by interfering with complex I of the respiratory chain. Mycotoxin. Acts as nephrotoxin in all species in which it has been tested. Has been implicated as a cause of Balkan nephropathy and yellow rice fever in humans. Induces apoptosis.
Product Specific Literature References
Mechanism of citrinin-induced dysfunction of mitochondria. III. Effects on renal cortical and liver mitochondrial swelling:
G.M. Chagas, et al.; J. Appl. Toxicol.
15
, 91 (1995)
Abstract
Mycotoxins:
J.W. Bennett & M. Klich; Clin. Microbiol. Rev.
16
, 497 (2003)
Abstract
Citrinin induces apoptosis in HL-60 cells via activation of the mitochondrial pathway:
F.Y. Yu, et al.; Toxicol. Lett.
161
, 143 (2006)
Abstract
Citrinin induces apoptosis via a mitochondria-dependent pathway and inhibition of survival signals in embryonic stem cells, and causes developmental injury in blastocysts:
W.H. Chan; Biochem. J.
404
, 317 (2007)
Abstract
Further Categories Containing This Product:
Mycotoxins
•
Respiratory Chain Other Products
•
Antibiotics - Apoptosis Inducers & Inhibitors
ALX-380-075
Revised 03-Apr-08
Antimycin A
SYNONYMS
Antipiricullin
Virosin
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antibiotics - Apoptosis Inducers & Inhibitors
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
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ALX-380-075-M005
5 mg
20.00 USD
ALX-380-075-M010
10 mg
33.00 USD
Product Specification
CAS NUMBER:
1397-94-0
MERCK INDEX:
14:
714 (A1) & 715 (A3)
RTECS:
CD0350000
SOURCE/HOST:
Isolated from
Streptomyces sp
. Mixture of antimycin A's.
APPEARANCE:
White to faint yellow powder.
SOLUBILITY:
Soluble in 100% ethanol (50mg/ml).
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
HANDLING:
Protect from light.
HAZARD:
TOXIC.
Product Description
Antibiotic. Induces apoptosis, which is not prevented by the presence of Bcl-2. Inhibits mitochondrial electron transport specifically between cytochromes b and c1.
Product Specific Literature References
The isolation and properties of antimycin A:
B. R. Dunshee, et al.; J. Am. Chem. Soc.
71
, 2436 (1949)
The effect of antimycin A on mouse liver inner mitochondrial membrane channel activity:
M.L. Campo, et al.; J. Biol. Chem.
267
, 8123 (1992)
Abstract
;
Full Text
Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3:
S.P. Tzung, et al.; Nat. Cell Biol.
3
, 183 (2001)
Abstract
Biophysical characterization of recombinant human Bcl-2 and its interactions with an inhibitory ligand, antimycin A:
K.M. Kim, et al.; Biochemistry
40
, 4911 (2001)
Abstract
Synthetic peptides and non-peptidic molecules as probes of structure and function of Bcl-2 family proteins and modulators of apoptosis
:
D. Liu & Z. Huang; Apoptosis
6
, 453 (2001)
Abstract
Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3:
S.P. Tzung, et al.; Nat. Cell. Biol.
3
, 183 (2001)
Abstract
Oligomycin and antimycin A prevent nitric oxide-induced apoptosis by blocking cytochrome C leakage:
N. Dairaku, et al.; J. Lab. Clin. Med.
143
, 143 (2004)
Abstract
An ROS generator, antimycin A, inhibits the growth of HeLa cells via apoptosis:
W.H. Park, et al.; J. Cell. Biochem.
102
, 98 (2007)
Abstract
Further Categories Containing This Product:
Bcl-2 Family Modulators
•
Respiratory Chain Other Products
ALX-380-108
Revised 03-Apr-08
Atpenin A5
SYNONYMS
3-[(2
S
,4
S
,5
R
)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1
H
)-pyridinone
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antibiotics - Antifungal
Ordering Information
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Format:
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ALX-380-108-C250
250 µg
90.00 USD
Product Specification
FORMULA:
C
15
H
21
Cl
2
NO
5
MW:
366.2
CAS NUMBER:
119509-24-9
RTECS:
CJ8800000
SOURCE/HOST:
Produced by
Penicillium
sp.
PURITY:
≥85% (HPLC)
APPEARANCE:
Colorless oil.
SOLUBILITY:
Soluble in DMSO, methanol or 100% ethanol; insoluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Antibiotic. Potent and specific inhibitor of mitochondrial complex II (succinate-ubiquinone oxidoreductase).
Product Specific Literature References
Atpenins, new antifungal antibiotics produced by Penicillium sp. Production, isolation, physico-chemical and biological properties:
S. Omura, et al.; J. Antibiot.
41
, 1769 (1988)
Abstract
The structures of atpenins A4, A5 and B, new antifungal antibiotics produced by Penicillium sp:
H. Kumagai, et al.; J. Antibiot.
43
, 1553 (1990)
Abstract
Mechanism of action of atpenin B on Raji cells:
K. Oshino, et al.; J. Antibiot.
43
, 1064 (1990)
Abstract
Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase):
H. Miyadera, et al.; PNAS
100
, 473 (2003)
Abstract
Structural and computational analysis of the quinone-binding site of complex II (succinate-ubiquinone oxidoreductase): a mechanism of electron transfer and proton conduction during ubiquinone reduction:
R. Horsefield, et al.; J. Biol. Chem.
281
, 7309 (2006)
Abstract
;
Full Text
General Information
MANUFACTURER
Fungal strain courtesy of the Kitasato Institute, Tokyo.
Further Categories Containing This Product:
Respiratory Chain Other Products
ALX-380-207
Revised 03-Apr-08
Apoptolidin
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antibiotics - Apoptosis Inducers & Inhibitors
Ordering Information
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ALX-380-207-MC01
0.1 mg
290.00 USD
Product Specification
FORMULA:
C
58
H
96
O
21
MW:
1129.4
CAS NUMBER:
194874-06-1
SOURCE/HOST:
Isolated from
Amicolatopsis
sp. MST-AS5912.
PURITY:
≥95% (HPLC)
APPEARANCE:
White to off-white solid.
SOLUBILITY:
Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
HAZARD:
HARMFUL.
Product Description
Originally isolated from
Nocardiopsis
sp. Antibiotic. Potent and highly selective apoptosis inducer in several cancer cell lines. F
0
F
1
-ATPase inhibitor.
Product Specific Literature References
Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp:
J.W. Kim, et al.; J. Antibiot. (Tokyo)
50
, 6628 (1997)
Abstract
Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F(0)F(1)-ATPase:
A.R. Salomon, et al.; PNAS
97
, 14766 (2000)
Abstract
;
Full Text
Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase:
A.R. Salomon, et al.; Chem. Biol.
8
, 71 (2001)
Abstract
;
Full Text
Apoptolidin: induction of apoptosis by a natural product:
P.T. Daniel, et al.; Angew. Chem. Int. Ed. Engl.
45
, 872 (2006)
Abstract
Correlation of F0F1-ATPase inhibition and antiproliferative activity of apoptolidin analogues:
P.A. Wender, et al.; Org. Lett.
8
, 589 (2006)
Abstract
Further Categories Containing This Product:
Natural Products - ATPase Inhibitors
•
Antitumor Agents (Apoptosis Inducers)
•
Antitumor Antibiotics
•
Respiratory Chain Other Products
ALX-380-211
Revised 19-Feb-08
Venturicidin A
SYNONYMS
Aabomycin A1
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antibiotics - Antifungal
Ordering Information
Product Numbers:
Format:
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ALX-380-211-M001
1 mg
170.00 USD
Product Specification
FORMULA:
C
41
H
67
NO
11
MW:
750.0
CAS NUMBER:
33538-71-5
MERCK INDEX:
14:
9947
RTECS:
YX4556000
SOURCE/HOST:
Isolated from
Streptomyces
sp. MST-117594.
PURITY:
≥95% (HPLC)
APPEARANCE:
White to off-white solid.
SOLUBILITY:
Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Macrolide antibiotic. Potent inhibitor of mitochondrial ATP synthase complex, acting on the F
0
membrane sector. Shows antifungal activity.
Product Specific Literature References
Venturicidin: a new antifungal antibiotic of potential use in agriculture:
A. Rhodes, et al.; Nature
192
, 952 (1961)
Abstract
Inhibition of Escherichia coli H+-ATPase by venturicidin, oligomycin and ossamycin:
D.S. Perlin, et al.; Biochim. Biophys. Acta
807
, 238 (1985)
Abstract
Amino acid substitutions in mitochondrial ATP synthase subunit 9 of Saccharomyces cerevisiae leading to venturicidin or ossamycin resistance:
M. Galanis, et al.; FEBS Lett.
249
, 333 (1989)
Abstract
;
Full Text
Studies on the mechanism of oxidative phosphorylation. ATP synthesis by submitochondrial particles inhibited at F0 by venturicidin and organotin compounds:
A. Matsuno-Yagi and Y. Hatefi; J. Biol. Chem.
268
, 6168 (1993)
Abstract
;
Full Text
Potassium selective and venturicidin sensitive conductances of Fo purified from bovine heart mitochondria, reconstituted in planar lipid bilayers:
H. Miedema, et al.; BBRC
203
, 1005 (1994)
Abstract
Further Categories Containing This Product:
Respiratory Chain Other Products
ALX-380-223
Revised 19-Feb-08
Venturicidin B
SYNONYMS
Aabomycin A2
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antibiotics - Antifungal
Ordering Information
Product Numbers:
Format:
Size:
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ALX-380-223-MC25
0.25 mg
360.00 USD
Product Specification
FORMULA:
C
40
H
66
O
10
MW:
706.9
CAS NUMBER:
33538-72-6
MERCK INDEX:
14:
9947
SOURCE/HOST:
Isolated from
Streptomyces
sp. MST-117594.
PURITY:
≥95% (HPLC)
APPEARANCE:
White to off-white solid.
SOLUBILITY:
Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Macrolide antibiotic. Potent inhibitor of mitochondrial ATP synthase complex, acting on the F
0
membrane sector. Shows antifungal activity.
Product Specific Literature References
Venturicidin: a new antifungal antibiotic of potential use in agriculture:
A. Rhodes, et al.; Nature
192
, 952 (1961)
Abstract
Inhibition of Escherichia coli H+-ATPase by venturicidin, oligomycin and ossamycin:
D.S. Perlin, et al.; Biochim. Biophys. Acta
807
, 238 (1985)
Abstract
Amino acid substitutions in mitochondrial ATP synthase subunit 9 of Saccharomyces cerevisiae leading to venturicidin or ossamycin resistance:
M. Galanis, et al.; FEBS Lett.
249
, 333 (1989)
Abstract
;
Full Text
Studies on the mechanism of oxidative phosphorylation. ATP synthesis by submitochondrial particles inhibited at F0 by venturicidin and organotin compounds:
A. Matsuno-Yagi and Y. Hatefi; J. Biol. Chem.
268
, 6158 (1993)
Abstract
;
Full Text
Potassium selective and venturicidin sensitive conductances of Fo purified from bovine heart mitochondria, reconstituted in planar lipid bilayers:
H. Miedema, et al.; BBRC
203
, 1005 (1994)
Abstract
Further Categories Containing This Product:
Respiratory Chain Other Products
ALX-380-229
Revised 14-Jan-08
Isoapoptolidin
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antibiotics - Apoptosis Inducers & Inhibitors
Ordering Information
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ALX-380-229-MC01
0.1 mg
320.00 USD
Product Specification
FORMULA:
C
58
H
96
O
21
MW:
1129.4
CAS NUMBER:
476647-30-0
SOURCE/HOST:
Isolated from
Amycolatopsis
sp. MST-AS5912.
PURITY:
≥90% (HPLC)
APPEARANCE:
White to off-white powder.
SOLUBILITY:
Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Isomer of apoptolidin (Prod. No.
ALX-380-207
). In water an equilibrium mixture of apoptolidin:isoapoptolidin (~1.5:1) is formed within hours. Less active F
0
F
1
-ATPase inhibitor (IC
50
=17µM) than apoptolidin (IC
50
=0.7µM).
Product Specific Literature References
Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin:
J.D. Pennington, et al.; Org. Lett.
4
, 3823 (2002)
Abstract
Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin:
P.A. Wender, et al.; Org. Lett.
4
, 3819 (2002)
Abstract
Further Categories Containing This Product:
Respiratory Chain Other Products
ALX-380-235
Revised 20-Jun-08
Piericidin A
SYNONYMS
Piericidin A1
Shaoguanmycin B
Antibiotic MT 1882-I
Antibiotic SN 198E
Antibiotic IT 143D
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Antitumor Antibiotics
Ordering Information
Product Numbers:
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ALX-380-235-M002
2 mg
140.00 USD
Product Specification
FORMULA:
C
25
H
37
NO
4
MW:
415.6
CAS NUMBER:
2738-64-9
RTECS:
YD4588000
SOURCE/HOST:
Isolated from
Streptomyces
sp. MST-AS5364.
PURITY:
≥95% (HPLC)
APPEARANCE:
Pale yellow oil.
SOLUBILITY:
Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
HAZARD:
VERY TOXIC.
Product Description
Antibiotic. Specific and potent inhibitor of NADH-ubiquinone oxidoreductase (complex I) that binds to ubiquinone binding site(s). Inhibits both mitochondrial and bacterial NADH ubiquinone oxidoreductase. Anticancer agent that prevents up-regulation of GRP78, and exhibits cytotoxic activity for etoposide resistant cancer cells under glucose-deprived conditions.
Product Specific Literature References
Piericidin A: a new inhibitor of mitochondrial electron transport:
C. Hall, et al.; BBRC
25
, 373 (1966)
Abstract
Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase:
T. Friedrich, et al.; Eur. J. Biochem.
219
, 691 (1994)
Abstract
The 49-kDa subunit of NADH-ubiquinone oxidoreductase (Complex I) is involved in the binding of piericidin and rotenone, two quinone-related inhibitors:
E. Darrouzet, et al.; FEBS Lett.
431
, 34 (1998)
Abstract
;
Full Text
Evidence for a quinone binding site close to the interface between NUOD and NUOB subunits of Complex I:
I. Prieur, et al.; Biochim. Biophys. Acta
1504
, 173 (2001)
Abstract
Etoposide-resistant HT-29 human colon carcinoma cells during glucose deprivation are sensitive to piericidin A, a GRP78 down-regulator:
J.H. Hwang, et al.; J. Cell. Physiol.
215
, 243 (2008)
Abstract
Further Categories Containing This Product:
Respiratory Chain Other Products
ALX-385-029
Revised 08-Apr-08
4’-Bromoflavone
SYNONYMS
4’-Bromo-2-phenylbenzopyran
4’-Bromo-2-phenyl-4
H
-1-benzopyran-4-one
PRODUCT LINE
Natural Products / Antibiotics
PRODUCT CATEGORY
Flavonoids/Related Products
Ordering Information
Product Numbers:
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ALX-385-029-G001
1 g
90.00 USD
Product Specification
FORMULA:
C
15
H
9
BrO
2
MW:
301.1
SOURCE/HOST:
Synthetic.
PURITY:
≥98%
APPEARANCE:
White to off-white solid.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
HAZARD:
IRRITANT.
Product Description
Chemopreventive compound. Potent inducer of phase II detoxifying enzymes. Quininone reductase and glutathione S-transferase in cell culture and different tissues of rats. Aryl hydrocarbon hydroxylase inducer.
Product Specific Literature References
Simple vs. complex inheritance of inducible aryl hydrocarbon hydroxylase in mouse tissues:
K. Burki, et al.; Biochem. Genet.
13
, 417 (1975)
Abstract
Cancer chemopreventive activity mediated by 4’-bromoflavone, a potent inducer of phase II detoxification enzymes:
L.L. Song, et al.; Cancer Res.
59
, 578 (1999)
Abstract
Further Categories Containing This Product:
Respiratory Chain Other Products
•
Natural Products - Chemopreventive Agents
ALX-430-130
Revised 09-Nov-06
HQNO
SYNONYMS
2-n-Heptyl-4-hydroxyquinoline N-oxide
PRODUCT LINE
