ALEXIS Biochemicals: Cyclosporin H

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ALX-350-128

Revised 03-Apr-08

Chetomin
SYNONYMS	Chaetomin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-128-M001		1 mg	185.00 USD
ALX-350-128-M005		5 mg	495.00 USD

Product Specification

FORMULA:	C₃₁H₃₀N₆O₆S₄
MW:	710.9
CAS NUMBER:	1403-36-7
SOURCE/HOST:	Isolated from Chaetomium species.
PURITY:	≥98% (HPLC)
APPEARANCE:	Off-white to fawn solid.
SOLUBILITY:	Soluble in DMSO, ethyl acetate or pyridine; fairly soluble in methanol, 100% ethanol; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	TOXIC.
IDENTITY:	Determined by ¹H-NMR.

Product Description

Dithiodiketopiperazine inhibitor of HIF-1 formation by disrupting the binding of p300 to both HIF-1α and HIF-2α. Inhibitor of tumor growth. Potent immunosuppressor. Antibacterial.

Product Specific Literature References

The structure of chetomin: A.G. McInnes, et al.; JACS 98, 6741 (1976) Abstract
Effects of chetomin on growth and acidic fermentation products of rumen bacteria: W.C. Jen and G.A. Jones; Can. J. Microbiol. 29, 1399 (1983) Abstract
Small molecule blockade of transcriptional coactivation of the hypoxia-inducible factor pathway: A.L. Kung, et al.; Cancer Cell 6, 33 (2004) Abstract
Immunomodulatory constituents from an Ascomycete, Chaetomium seminudum: H. Fujimoto, et al.; J. Nat. Prod. 67, 98 (2004) Abstract
Effects of HIF-1 inhibition by chetomin on hypoxia-related transcription and radiosensitivity in HT 1080 human fibrosarcoma cells: A. Staab, et al.; BMC Cancer 7, 213 (2007) Abstract; Full Text

Further Categories Containing This Product:

Hypoxia-inducible Factor [HIF] / Related Products • Antitumor Antibiotics • Immunomodulators Other Products • Antitumor Agents (Anti-proliferative)

ALX-350-239

Revised 22-Apr-08

Gliotoxin
SYNONYMS	[3R-(3α, 5aβ,6β,10aα)]-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epi-dithiopyrazino[1,2-a]indole-1,4-dione
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Apoptosis Inducers & Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-239-M001		1 mg	60.00 USD

Product Specification

FORMULA:	C₁₃H₁₄N₂O₄S₂
MW:	326.4
CAS NUMBER:	67-99-2
MERCK INDEX:	14: 4441
RTECS:	KB4725000
SOURCE/HOST:	Isolated from Gladiocladium fimbriatum.
PURITY:	≥98% (HPLC)
APPEARANCE:	White to light yellow solid.
SOLUBILITY:	Soluble in DMSO or methanol (10mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
USE/STABILITY:	Stock solutions are stable for up to 3 months when stored at -20°C.
HAZARD:	TOXIC.

Product Description

Immunomodulating mycotoxin which acts by blocking membrane thiol groups. Causes apoptotic cell death in macrophages and thymocytes. Induces Ca²⁺ release from intact rat liver mitochondria. Inhibits the activation of transcription factor NF-κB. Antioxidant.

Product Specific Literature References

Identification of an agent in cultures of Aspergillus fumigatus displaying anti-phagocytic and immunomodulating activity in vitro: A. Müllbacher, et al.; J. Gen. Microbiol. 131, 1251 (1985) Abstract
R.J. Jones & J.G. Hancock; J. Gen. Microbiol. 134, 2067 (1988)
Gliotoxin stimulates Ca2+ release from intact rat liver mitochondria: M. Schweizer & C. Richter; Biochemistry 33, 13401 (1994) Abstract
Extracellular calcium is not required for gliotoxin or dexamethasone- induced DNA fragmentation: a reappraisal of the use of EGTA: P. Waring & A. Sjaarda; Int. J. Immunopharmacol. 17, 403 (1995) Abstract
Gliotoxin and related epipolythiodioxopiperazines: P. Waring & J. Beaver; Gen. Pharmacol. 27, 1311 (1996), Review Abstract
The immunosuppressive fungal metabolite gliotoxin specifically inhibits transcription factor NF-kappaB: H.L. Pahl, et al.; J.Exp. Med. 183, 1829 (1996) Abstract
Aspergillus fumigatus suppresses the human cellular immune response via gliotoxin-mediated apoptosis of monocytes: M. Stanzani, et al.; Blood 105, 2258 (2005) Abstract
Discovery of gliotoxin as a new small molecule targeting thioredoxin redox system: H.S. Choi, et al.; BBRC 359, 523 (2007) Abstract

Further Categories Containing This Product:

Antioxidants, Flavonoids & Free Radical Scavengers Other Products • Natural Products - NF-kB Pathway Inhibitors • Mycotoxins • Antibiotics - Immunomodulators

ALX-380-002

Revised 03-Apr-08

Cyclosporin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-002-M100		100 mg	46.00 USD
ALX-380-002-5100		5x100 mg	190.00 USD
ALX-380-002-G001		1 g	290.00 USD
ALX-380-002-5001		5x1 g	1'150.00 USD

Product Specification

FORMULA:	C₆₂H₁₁₁N₁₁O₁₂
MW:	1202.6
CAS NUMBER:	59865-13-3
MERCK INDEX:	14: 2752
RTECS:	GZ4120000
SOURCE/HOST:	Isolated from Fusarium solani.
PURITY:	≥99% (Assay)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in methanol, 100% ethanol, acetone or petroleum ether; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	MAY BE TERATOGENIC. TOXIC. MAY BE CARCINOGENIC.

Product Description

Antibiotic. Potent immunosuppressor. Widely used after organ transplantation. Binds to cytosolic proteins of the cyclophilin family. Cyclosporin A-cyclophilin complexes block protein phosphatase 2B (PP2B; calcineurin), a key enzyme in T cell activation. As a result of the calcineurin inhibition, cyclosporine A blocks various cellular processes such as activation of T cells and expression of several lymphokines (especially IL-2). Inhibits cytochrome c release from mitochondria. Inhibits nitric oxide (NO) synthesis.

Product Specific Literature References

Cyclosporin A and C-New metabolites from Trichodermapolysporum (Link ex Pers.) Rifai: Dreyfuss M., et al.; Europ. J. appl. Microbiol. 3, 125 (1976)
Immunosuppression for organ grafting - observations on cyclosporin A: R. Y. Calne; Immunol. Rev. 46, 113 (1976), Review Abstract
Immunological actions of cyclosporin A in rheumatoid arthritis: D. Yocum; Br. J. Rheumatol. 32, 38 (1993), Review Abstract
Cyclosporin A binding to mitochondrial cyclophilin inhibits the permeability transition pore and protects hearts from ischaemia/reperfusion injury: A.P. Halestrap, et al; Mol. Cell. Biochem. 174, 167 (1997), Review Abstract
New aspects of cyclosporin a mode of action: from gene silencing to gene up-regulation: L. Mascarell & P. Truffa-Bachi; Mini Rev. Med. Chem. 3, 205 (2003), Review Abstract
Rationale for T cell inhibition by cyclosporin A in major autoimmune diseases: G.F. Ferraccioli, et al.; Ann. N. Y. Acad. Sci. 1051, 658 (2005), Review Abstract

Further Categories Containing This Product:

MPTP [Mitochondrial Transition Pore] / Related Products • Antibiotics - Nitric Oxide Pathway Modulators • Antibiotics - Apoptosis Inducers & Inhibitors • Non-apoptotic Cell Death / Necrosis

ALX-380-004

Revised 21-Feb-08

Rapamycin
SYNONYMS	Sirolimus AY-22,989 RAPA Rapamune
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-004-C100		100 µg	35.00 USD
ALX-380-004-5100		5x100 µg	90.00 USD
ALX-380-004-M001		1 mg	120.00 USD
ALX-380-004-M005		5 mg	420.00 USD
ALX-380-004-M025		25 mg	950.00 USD

Product Specification

FORMULA:	C₅₁H₇₉NO₁₃
MW:	914.2
CAS NUMBER:	53123-88-9
MERCK INDEX:	14: 8114
RTECS:	VE6250000
SOURCE/HOST:	Isolated from Streptomyces hygroscopicus.
PURITY:	≥98% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in chloroform, DMSO or methanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	TOXIC.

Product Description

Macrocyclic-triene antibiotic possessing potent immunosuppressant activity. It forms a complex with FKBP12 that binds to an effector, thus inhibiting IL-2 and other growth promoting lymphokines. The effectors were recently identified as FRAP (FKBP12 rapamycin-associated protein) and RAFT1 (rapamycin and KFBP12 target). Rapamycin induces inhibition of p70^s6k, p33^cdk2 and p34^cdc2. Enhances apoptosis.

Product Specific Literature References

Rapamycin (AY-22,989), a new antifungal antibiotic. I. Taxonomy of the producing streptomycete and isolation of the active principle: C. Vezina, et al.; J. Antibiot. (Tokyo) 28, 721 (1975) Abstract
Rapamycin (AY-22,989), a new antifungal antibiotic. II. Fermentation, isolation and characterization: S.N. Sehgal, et al.; J. Antibiot. (Tokyo) 28, 727 (1975) Abstract
Rapamycin-induced inhibition of the 70-kilodalton S6 protein kinase: D.J. Price, et al.; Science 257, 973 (1992) Abstract
Rapamycin: in vitro profile of a new immunosuppressive macrolide: S.N. Sehgal & C.C. Bansback; Ann. N. Y. Acad. Sci. 685, 58 (1993) Abstract
Rapamycin inhibition of interleukin-2-dependent p33cdk2 and p34cdc2 kinase activation in T lymphocytes: W.G. Morice, et al.; J. Biol. Chem. 268, 22737 (1993) Abstract; Full Text
A mammalian protein targeted by G1-arresting rapamycin-receptor complex: E.J. Brown, et al.; Nature 369, 756 (1994) Abstract
RAFT1: a mammalian protein that binds to FKBP12 in a rapamycin- dependent fashion and is homologous to yeast TORs: D.M. Sabatini, et al.; Cell 78, 35 (1994) Abstract
Rapamycin, a potent immunosuppressive drug, causes programmed cell death in B lymphoma cells: S. Muthukkumar, et al.; Transplantation 60, 264 (1995) Abstract
Rapamycin enhances apoptosis and increases sensitivity to cisplatin in vitro: Y. Shi, et al.; Cancer Res. 55, 1982 (1995) Abstract
Rapamycin potentiates dexamethasone-induced apoptosis and inhibits JNK activity in lymphoblastoid cells: T. Ishizuka, et al.; BBRC 230, 386 (1997) Abstract
Rapamycin and p53 act on different pathways to induce G1 arrest in mammalian cells: S.M. Metcalfe, et al.; Oncogene 15, 1635 (1997) Abstract
Rapamycin inhibition of the G1 to S transition is mediated by effects on cyclin D1 mRNA and protein stability: S. Hashemolhosseini, et al.; J. Biol. Chem. 273, 14424 (1998) Abstract; Full Text
Rapamycin causes poorly reversible inhibition of mTOR and induces p53- independent apoptosis in human rhabdomyosarcoma cells: H. Hosoi, et al.; Cancer Res. 59, 886 (1999) Abstract
Rapamycin: an anti-cancer immunosuppressant?: B.K. Law; Crit. Rev. Oncol. Hematol. 56, 47 (2005), Review Abstract
mTOR inhibitors (rapamycin and its derivatives) and nitrogen containing bisphosphonates: bi-functional compounds for the treatment of bone tumours: B. Ory, et al.; Curr. Med. Chem. 14, 1381 (2007), Review Abstract

Further Categories Containing This Product:

Mammalian Target of Rapamycin [mTOR] / Related Products • Antibiotics - Protein Kinase Inhibitors • Antibiotics - Antifungal

ALX-380-005

Revised 03-Apr-08

Ascomycin
SYNONYMS	Immunomycin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-005-M001		1 mg	125.00 USD
ALX-380-005-M005		5 mg	540.00 USD

Product Specification

FORMULA:	C₄₃H₆₉NO₁₂
MW:	792.0
CAS NUMBER:	11011-38-4
RTECS:	CI75700000
SOURCE/HOST:	Isolated from Streptomyces sp.
PURITY:	≥95%
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	HARMFUL.

Product Description

Antibiotic. Ethyl analog of FK506 (Prod. No. ALX-380-008) with similar immunosuppressant properties. Inhibits calcineurin phosphatase.

Product Specific Literature References

Ascomycin, an antifungal antibiotic: T. Arai, et al.; J. Antibiot. (Tokyo) 15, 23 (1962) Abstract
NMR studies of an FK-506 analog, [U-13C]ascomycin, bound to FK-506-binding protein: A.M. Petros, et al.; J. Med. Chem. 35, 2467 (1992) Abstract
Structure-activity profiles of macrolactam immunosuppressant FK-506 analogues: M. Kawai, et al.; FEBS Lett. 316, 107 (1993) Abstract
Enzymatic synthesis and immunosuppressive activity of novel desmethylated immunomycins (ascomycins): A. Shafiee, et al.; J. Antibiot. (Tokyo) 46, 1397 (1993) Abstract

Further Categories Containing This Product:

PP2B [Calcineurin] / Related Products • Antibiotics - Other Signal Transduction Pathway Modulators

ALX-380-008

Revised 05-Apr-08

FK506
SYNONYMS	Tacrolimus
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-008-M001		1 mg	30.00 USD
ALX-380-008-M005		5 mg	60.00 USD
ALX-380-008-M025		25 mg	180.00 USD

Product Specification

FORMULA:	C₄₄H₆₉NO₁₂ . H₂O
MW:	804.0 . 18.0
CAS NUMBER:	104987-11-3
MERCK INDEX:	14: 9025
RTECS:	KD4200000
PURITY:	≥98%
APPEARANCE:	White to off-white crystalline powder.
SOLUBILITY:	Soluble in DMSO, 100% ethanol, methanol, ethyl acetate or acetone; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
HAZARD:	HARMFUL. MAY BE CARCINOGENIC. IRRITANT.

Product Description

Immunosuppressant that blocks T cell proliferation in vitro by inhibiting the generation of several lymphokines, especially IL-2. Shown to inhibit the activity of FK506 binding protein and to inhibit the Ca²⁺-dependent phosphatase and protein phosphatase 2B (PP2B; calcineurin). Activates NF-κB through phosphorylation and degradation of IκBα.

Product Specific Literature References

FK-506, a novel immunosuppressant isolated from a Streptomyces. I. Fermentation, isolation, and physico-chemical and biological characteristics: T. Kino, et al.; J. Antibiot. (Tokyo) 40, 1249 (1987) Abstract
Cyclosporin A and FK506: molecular mechanisms of immunosuppression and probes for transplantation biology: B.E. Bierer, et al.; Curr. Opin. Immunol. 5, 763 (1993) Abstract
Cyclosporin A, FK506 and rapamycin: more than just immunosuppression: J. Kunz and M.N. Hall; TIBS 18, 334 (1993) Abstract
Immunosuppressant FK506 activates NF-kappaB through the proteasome-mediated degradation of IkappaBalpha. Requirement for Ikappabalpha n-terminal phosphorylation but not ubiquitination sites: Y. Zhang, et al.; J. Biol. Chem. 274, 34657 (1999) Abstract; Full Text
FK506, an immunosuppressant targeting calcineurin function: F.J. Dumont; Curr. Med. Chem. 7, 731 (2000) Abstract
FK506 and its analogs - therapeutic potential for neurological disorders: A. Klettner and T. Herdegen; Curr. Drug Targets CNS Neurol. Disord. 2, 153 (2003), Review Abstract
A review of the action of tacrolimus (FK506) on experimental models of rheumatoid arthritis: S. Miyata, et al.; Inflamm. Res. 54, 1 (2005), Review Abstract

Further Categories Containing This Product:

NF-kB Pathway Inhibitors • PP2B [Calcineurin] / Related Products • Antibiotics - NF-kB Inhibitors

ALX-380-015

Revised 08-Oct-07

Mycophenolic acid
SYNONYMS	6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexanoic acid
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-015-M050		50 mg	30.00 USD
ALX-380-015-M250		250 mg	105.00 USD
ALX-380-015-G001		1 g	310.00 USD

Product Specification

FORMULA:	C₁₇H₂₀O₆
MW:	320.3
CAS NUMBER:	24280-93-1
MERCK INDEX:	14: 6327
SOURCE/HOST:	Isolated from Penicillium brevi-compactum.
PURITY:	≥98%
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in methanol or methylene chloride; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+20°C
HAZARD:	TOXIC.

Product Description

Immunosuppressive agent that inhibits de novo purine nucleotide synthesis via inhibition of inosine-5’-monophosphate (IMP). Prevents the formation of xanthosine-5’-monophosphate (XMP) and guanosine-5’-monophosphate (GMP). Depletes tetrahydrobiopterin and decreases nitric oxide (NO) production by iNOS (NOS II) without affecting nNOS (NOS I) activity. Suppresses cytokine-induced nitric oxide (NO) production in mouse and rat vascular endothelial cells.

Product Specific Literature References

Guanine nucleotide depletion and toxicity in mouse T lymphoma (S-49) cells: M.B. Cohen, et al.; J. Biol. Chem. 256, 8713 (1981) Abstract; Full Text
Pharmacodynamic assessment of mycophenolic acid-induced immunosuppression by measuring IMP dehydrogenase activity: L.J. Langman, et al.; Clin. Chem. 41, 295 (1995) Abstract
Mycophenolic acid, an inhibitor of IMP dehydrogenase that is also an immunosuppressive agent, suppresses the cytokine-induced nitric oxide production in mouse and rat vascular endothelial cells: M. Senda, et al.; Transplantation 60, 1143 (1995) Abstract
Mycophenolate mofetil and its mechanisms of action: A.C. Allison & E.M. Eugui; Immunopharmacology 47, 85 (2000) Abstract
Mycophenolic acid downregulates inducible nitric oxide synthase induction in astrocytes: D. Miljkovic, et al.; Glia 39, 247 (2002) Abstract
Mycophenolic acid inhibits inosine 5´-monophosphate dehydrogenase and suppresses production of pro-inflammatory cytokines, nitric oxide, and LDH in macrophages: C.A. Jonsson & H. Carlsten; Cell Immunol. 216, 93 (2002) Abstract
Inducible nitric oxide synthase inhibition by mycophenolic acid: D. Miljkovic, et al.; Mini Rev. Med. Chem. 4, 741 (2004), Review Abstract
Antifibrotic actions of mycophenolic acid: C. Morath, et al.; Clin. Transplant. 20, 25 (2006), Review Abstract

Further Categories Containing This Product:

Antibiotics - Nitric Oxide Pathway Modulators • Phenolic Acids

ALX-380-042

Revised 05-May-08

Doxorubicin . hydrochloride
SYNONYMS	DXR . HCl 14-Hydroxydaunomycin . HCl Adriamycin . HCl
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-042-M005		5 mg	60.00 USD
ALX-380-042-M010		10 mg	110.00 USD
ALX-380-042-M025		25 mg	250.00 USD

Product Specification

FORMULA:	C₂₇H₂₉NO₁₁ . HCl
MW:	543.5 . 36.5
CAS NUMBER:	25316-40-9
MERCK INDEX:	14: 3439
RTECS:	QI9295900
SOURCE/HOST:	Isolated from Streptomyces peucetius var. caesius.
PURITY:	≥98%
APPEARANCE:	Red solid.
SOLUBILITY:	Soluble in water.
SHIPPING:	AMBIENT