ALEXIS Biochemicals: Xanthohumol

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ALX-350-270

Revised 08-Feb-08

α-Amanitin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Natural Products - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-270-M001		1 mg	140.00 USD

Product Specification

FORMULA:	C₃₉H₅₄N₁₀O₁₄S
MW:	919.0
CAS NUMBER:	23109-05-9
MERCK INDEX:	14: 373
RTECS:	BD6195000
SOURCE/HOST:	Isolated from Amanita phalloides mushrooms.
PURITY:	≥90%
APPEARANCE:	White to light yellow powder.
SOLUBILITY:	Soluble in 100% ethanol (5mg/ml), DMSO, dimethyl formamide, methanol or water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Dilute with buffer immediately prior to use. Product is destroyed by concentrated acid or base.
HANDLING:	Protect from light.
HAZARD:	VERY TOXIC.

Product Description

Inhibits eukaryotic RNA-polymerase II with high efficiency, but not eukaryotic RNA-polymerase I, or bacterial or viral RNA-polymerases. Inhibits mammalian protein synthesis.

Product Specific Literature References

Effect of alpha-amanitin on ribonucleic acid synthesis and on ribonucleic acid polymerase in mouse liver: F. Stirpe & L. Fiume; Biochem. J. 103, 67P (1967) Abstract
Specific inhibition of nuclear RNA polymerase II by alpha-amanitin: T.J. Lindell, et al.; Science 170, 447 (1970) Abstract
Fifty years of amanitin: T. Wieland & H. Faulstich; Experientia 47, 1189 (1991), (Review) Abstract
Alpha-amanitin blocks translocation by human RNA polymerase II: X.Q. Gong, et al.; J. Biol. Chem. 279, 27422 (2004) Abstract

Further Categories Containing This Product:

Amanitins & Phalloidins / Related Products • RNA Polymerases / Related Products • Protein Synthesis Other Products

ALX-350-271

Revised 08-Oct-07

β-Amanitin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Natural Products - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-271-M001		1 mg	170.00 USD

Product Specification

FORMULA:	C₃₉H₅₃N₉O₁₅S
MW:	920.0
CAS NUMBER:	21150-22-1
MERCK INDEX:	14: 373
SOURCE/HOST:	Isolated from Amanita phalloides mushrooms.
PURITY:	≥90%
FORMULATION:	White to off-white powder.
SOLUBILITY:	Soluble in DMSO, dimethyl formamide, methanol or water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Dilute with buffer immediately prior to use. Product is destroyed by concentrated acid or base.
HANDLING:	Protect from light.
HAZARD:	VERY TOXIC.

Product Description

Biological activity like α-amanitin (Prod. No. ALX-350-270), but contains a carboxy group which is useful for coupling reactions.

Further Categories Containing This Product:

Amanitins & Phalloidins / Related Products • RNA Polymerases / Related Products • Protein Synthesis Other Products

ALX-350-272

Revised 17-Dec-07

γ-Amanitin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Natural Products - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-272-M001		1 mg	170.00 USD

Product Specification

FORMULA:	C₃₉H₅₄N₁₀O₁₃S
MW:	903.0
CAS NUMBER:	13567-11-8; 21150-23-2
MERCK INDEX:	14: 373
SOURCE/HOST:	Isolated from Amanita phalloides mushrooms.
PURITY:	≥90%
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in DMSO, dimethyl formamide or methanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Dilute with buffer immediately prior to use. Product is destroyed by concentrated acid or base.
HANDLING:	Protect from light.
HAZARD:	VERY TOXIC.

Product Description

Biological activity like α-amanitin (Prod. No. ALX-350-270).

Further Categories Containing This Product:

Amanitins & Phalloidins / Related Products • RNA Polymerases / Related Products • Protein Synthesis Other Products

ALX-350-095

Revised 03-Apr-08

Apicidin
SYNONYMS	cyclo-L-(2-Amino-8-oxodecanoyl)-L-(N-methoxy-tryptophan)-L-isoleucyl-D-pipecolinyl
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Natural Products - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-095-M001		1 mg	50.00 USD
ALX-350-095-M005		5 mg	200.00 USD

Product Specification

FORMULA:	C₃₄H₄₉N₅O₆
MW:	623.8
CAS NUMBER:	183506-66-3
SOURCE/HOST:	Isolated from Fusarium sp.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	VERY TOXIC.

Product Description

Potent inhibitor of histone deacetylase (HDAC). Inhibits proliferation. Induces cell cycle arrest. Stimulates apoptosis of cancer cells. Antiprotozoal.

Product Specific Literature References

Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase: S.J. Darkin-Rattray, et al.; PNAS 93, 13143 (1996) Abstract
Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin: J.W. Han, et al.; Cancer Res. 60, 6068 (2000) Abstract
Transcriptional activation of p21(WAF1/CIP1) by apicidin, a novel histone deacetylase inhibitor: J.S. Kim, et al.; BBRC 281, 866 (2001) Abstract
Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure-activity relationships of apicidin. Part 1: S.L. Colletti, et al.; Bioorg. Med. Chem. Lett. 11, 107 (2001) Abstract
Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure-activity relationships of apicidin. Part 2: S.L. Colletti, et al.; Bioorg. Med. Chem. Lett. 11, 113 (2001) Abstract
Structure and chemistry of apicidins, a class of novel cyclic tetrapeptides without a terminal alpha-keto epoxide as inhibitors of histone deacetylase with potent antiprotozoal activities: S.B. Singh, et al.; J. Org. Chem. 67, 815 (2002) Abstract
Apicidin, a histone deacetylase inhibitor, induces differentiation of HL-60 cells: J. Hong, et al.; Cancer Lett. 189, 197 (2003) Abstract
Activation of NF-kappaB by HDAC inhibitor apicidin through Sp1-dependent de novo protein synthesis: its implication for resistance to apoptosis: Y.K. Kim, et al.; Cell Death Differ. 13, 2033 (2006) Abstract
Apicidin, a novel histone deacetylase inhibitor, has profound anti-growth activity in human endometrial and ovarian cancer cells: T. Ueda, et al.; Int. J. Mol. Med. 19, 301 (2007) Abstract

Further Categories Containing This Product:

Cell Cycle Blockers & Inhibitors / Related Products • HDAC Inhibitors • Natural Products for Cell Cycle Research • Natural Products - Other Anti-infective Agents • Parasitic Diseases Other Products • Natural Products - Apoptosis Inducers & Inhibitors

ALX-350-277

Revised 03-Apr-08

Betulinic acid (high purity)
SYNONYMS	3β-Hydroxy-20(29)-lupaene-28-oic acid
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-277-M005		5 mg	32.00 USD
ALX-350-277-M025		25 mg	95.00 USD
ALX-350-277-M100		100 mg	290.00 USD

Product Specification

FORMULA:	C₃₀H₄₈O₃
MW:	456.7
CAS NUMBER:	472-15-1
SOURCE/HOST:	Isolated from Platanus acerifolia (plane) tree bark.
PURITY:	≥99%
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	Keep cool and dry.
HAZARD:	IRRITANT.

Product Description

Antitumor and anti-HIV agent. Induces apoptosis by activating mitochondrial permeability transition (MPT). Inhibits NF-κB activation and NF-κB-regulated gene expression induced by carcinogens and inflammatory stimuli. Decreases expression of Bcl-2 and cyclin D1. Potent proteasome activator.

Product Specific Literature References

Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids: T. Fujioka, et al.; J. Nat. Prod. 57, 243 (1994) Abstract
Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis: E. Pisha, et al.; Nat. Med. 1, 1046 (1995) Abstract
Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents: Y. Kashiwada, et al.; J. Med. Chem. 39, 1016 (1996) Abstract
Betulinic acid triggers CD95 (APO-1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors: S. Fulda, et al.; Cancer Res. 57, 4956 (1997) Abstract
Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives: F. Hashimoto, et al.; Bioorg. Med. Chem. 5, 2133 (1997) Abstract
Induction of p53 without increase in p21WAF1 in betulinic acid-mediated cell death is preferential for human metastatic melanoma: M. Rieber & M. Strasberg Rieber; DNA Cell Biol. 17, 399 (1998) Abstract
Betulinic acid induces apoptosis in human neuroblastoma cell lines: M.L. Schmidt, et al.; Eur. J. Cancer 33, 2007 (1997) Abstract
Activation of mitochondria and release of mitochondrial apoptogenic factors by betulinic acid: S. Fulda, et al.; J. Biol. Chem. 273, 33942 (1998) Abstract; Full Text
Betulinic acid inhibits aminopeptidase N activity: M.F. Melzig & H. Bormann; Planta Med. 64, 655 (1998) Abstract
Correspondence re: S. Fulda et al., Betulinic acid triggers CD95 (Apo1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors. Cancer Res., 57: 4956, 1997: M. Rieber & M. Strasberg Rieber; Cancer. Res. 58, 5876 (1998) Abstract
Betulinic acid: a new cytotoxic agent against malignant brain-tumor cells: S. Fulda, et al.; Int. J. Cancer 82, 435 (1999) Abstract
Betulinic acid-induced apoptosis in glioma cells: A sequential requirement for new protein synthesis, formation of reactive oxygen species, and caspase processing: W. Wick, et al.; J Pharmacol. Exp. Ther. 289, 1306 (1999) Abstract; Full Text
Effects of betulinic acid alone and in combination with irradiation in human melanoma cells: E. Selzer, et al.; J. Invest. Dermatol. 114, 935 (2000) Abstract
Betulinic acid suppresses carcinogen-induced NF-kappa B activation through inhibition of I kappa B alpha kinase and p65 phosphorylation: abrogation of cyclooxygenase-2 and matrix metalloprotease-9: Y. Takada & B.B. Aggarwal; J. Immunol. 171, 3278 (2003) Abstract
Inhibition of IkappaB kinase activity by acetyl-boswellic acids promotes apoptosis in androgen-independent PC-3 prostate cancer cells in vitro and in vivo: T. Syrovets, et al.; J. Biol. Chem. 280, 6170 (2005) Abstract
Induction of central signalling pathways and select functional effects in human platelets by beta-boswellic acid: D. Poeckel, et al.; Br. J. Pharmacol. 146, 514 (2005) Abstract
Betulinic acid and its derivatives: a review on their biological properties: P. Yogeeswari and D. Sriram; Curr. Med. Chem. 12, 657 (2005), Review Abstract
Betulinic acid and its derivatives, potent DNA topoisomerase II inhibitors, from the bark of Bischofia javanica: S. Wada & R. Tanaka; Chem. Biodivers. 2, 689 (2005) Abstract
Betulinic acid as new activator of NF-kappaB: molecular mechanisms and implications for cancer therapy: H. Kasperczyk, et al.; Oncogene 24, 6945 (2005) Abstract
Activation and inhibition of the proteasome by betulinic acid and its derivatives: L. Huang, et al.; FEBS Lett. 581, 4955 (2007) Abstract

Further Categories Containing This Product:

Other Natural Products - DNA Regulation / Transcription • Natural Products - NF-kB Pathway Inhibitors • MPTP [Mitochondrial Transition Pore] / Related Products • Natural Products - Anti-inflammatory Agents • NF-kB Pathway Inhibitors • Antitumor Agents (Apoptosis Inducers) • Natural Products - Antiviral / anti-HIV Agents • Natural Products - Apoptosis Inducers & Inhibitors • HIV / AIDS / Related Products

ALX-350-298

Revised 03-Apr-08

Betulinic acid (~95%)
SYNONYMS	3β-Hydroxy-20(29)-lupaene-28-oic acid
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-298-M100		100 mg	55.00 USD
ALX-350-298-M500		500 mg	180.00 USD
ALX-350-298-G001		1 g	290.00 USD

Product Specification

FORMULA:	C₃₀H₄₈O₃
MW:	456.7
CAS NUMBER:	472-15-1
SOURCE/HOST:	Isolated from Platanus acerifolia (plane tree) bark.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Product Specific Literature References

Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids: T. Fujioka, et al.; J. Nat. Prod. 57, 243 (1994) Abstract
Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis: E. Pisha, et al.; Nat. Med. 1, 1046 (1995) Abstract
Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents: Y. Kashiwada, et al.; J. Med. Chem. 39, 1016 (1996) Abstract
Betulinic acid triggers CD95 (APO-1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors: S. Fulda, et al.; Cancer Res. 57, 4956 (1997) Abstract
Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives: F. Hashimoto, et al.; Bioorg. Med. Chem. 5, 2133 (1997) Abstract
Betulinic acid induces apoptosis in human neuroblastoma cell lines: M.L. Schmidt, et al.; Eur. J. Cancer 33, 2007 (1997) Abstract
Induction of p53 without increase in p21WAF1 in betulinic acid-mediated cell death is preferential for human metastatic melanoma: M. Rieber & M. Strasberg Rieber; DNA Cell Biol. 17, 399 (1998) Abstract
Activation of mitochondria and release of mitochondrial apoptogenic factors by betulinic acid: S. Fulda, et al.; J. Biol. Chem. 273, 33942 (1998) Abstract; Full Text
Betulinic acid inhibits aminopeptidase N activity: M.F. Melzig & H. Bormann; Planta Med. 64, 655 (1998) Abstract
Correspondence re: S. Fulda et al., Betulinic acid triggers CD95 (Apo1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors. Cancer Res., 57: 4956, 1997: M. Rieber & M. Strasberg Rieber; Cancer. Res. 58, 5876 (1998) Abstract
Betulinic acid: a new cytotoxic agent against malignant brain-tumor cells: S. Fulda, et al.; Int. J. Cancer 82, 435 (1999) Abstract
Betulinic acid-induced apoptosis in glioma cells: A sequential requirement for new protein synthesis, formation of reactive oxygen species, and caspase processing: W. Wick, et al.; J Pharmacol. Exp. Ther. 289, 1306 (1999) Abstract; Full Text
Effects of betulinic acid alone and in combination with irradiation in human melanoma cells: E. Selzer, et al.; J. Invest. Dermatol. 114, 935 (2000) Abstract
Betulinic acid suppresses carcinogen-induced NF-kappa B activation through inhibition of I kappa B alpha kinase and p65 phosphorylation: abrogation of cyclooxygenase-2 and matrix metalloprotease-9: Y. Takada & B.B. Aggarwal; J. Immunol. 171, 3278 (2003) Abstract
Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection: R.H. Cichewicz & S.A. Kouzi; Med. Res. Rev. 24, 90 (2004), Review Abstract
Betulinic acid-induced apoptosis in leukemia cells: H. Ehrhardt, et al.; Leukemia 18, 1406 (2004) Abstract
Betulinic acid and its derivatives: a review on their biological properties: P. Yogeeswari & D. Sriram; Curr. Med. Chem. 12, 657 (2005), Review Abstract
Betulinic acid decreases expression of bcl-2 and cyclin D1, inhibits proliferation, migration and induces apoptosis in cancer cells: W. Rzeski, et al.; Naunyn Schmiedebergs Arch. Pharmacol. 374, 11 (2006) Abstract
Activation and inhibition of the proteasome by betulinic acid and its derivatives: L. Huang, et al.; FEBS Lett. 581, 4955 (2007) Abstract

Further Categories Containing This Product:

CDK & Cyclin Inhibitors • NF-kB Pathway Inhibitors • Other Natural Products - DNA Regulation / Transcription • Natural Products - NF-kB Pathway Inhibitors • MPTP [Mitochondrial Transition Pore] / Related Products • Natural Products - Anti-inflammatory Agents • Natural Products - Antiviral / anti-HIV Agents • Antitumor Agents (Apoptosis Inducers) • Ubiquitin & Proteasome Other Products • Natural Products - Apoptosis Inducers & Inhibitors • HIV / AIDS / Related Products

ALX-550-322

Revised 11-Nov-08

Caffeine
SYNONYMS	1,3,7-Trimethylxanthine 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products for Neurological Research

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-550-322-G005		5 g	10.00 USD

Product Specification

FORMULA:	C₈H₁₀N₄O₂
MW:	194.2
CAS NUMBER:	58-08-2
MERCK INDEX:	14: 1636
SOURCE/HOST:	Found in tea leaves, coffee beans, cocoa beans, maté leaves, guarana paste and kola nuts.
PURITY:	≥99%
APPEARANCE:	White to colorless powder.
SOLUBILITY:	Soluble in chloroform, 100% alcohol or hot water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+20°C
HAZARD:	HARMFUL.
IDENTITY:	Identity determined by NIR.

Product Description

CNS stimulant. Blocks adenosine A1 and A2A receptors. cAMP phosphodiesterase inhibitor. Interferes with the uptake and storage of Ca2+ by the sarcoplasmic reticulum in skeletal muscle. Prevents apoptosis and cell cycle effects induced by various chemicals. Inhibits cellular DNA repair mechanisms. Anti-inflammatory.

Product Specific Literature References

Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors: J.W. Daly, et al.; J. Med. Chem. 29, 1305 (1986) Abstract
Caffeine as an analgesic adjuvant: a review of pharmacology and mechanisms of action: J. Sawynok & T.L. Yaksh; Pharmacol. Rev. 45, 43 (1993) Abstract
Caffeine prevents apoptosis and cell cycle effects induced by camptothecin or topotecan in HL-60 cells: F. Traganos, et al.; Cancer Res. 53, 4613 (1993) Abstract
Multiple effects of caffeine on calcium current in rat ventricular myocytes: I. Zahradnik & P. Palade; Pfluegers Arch. 424, 129 (1993) Abstract
Acute effects of caffeine on arterial stiffness, wave reflections, and central aortic pressures: T.G. Papaioannou, et al.; Am. J. Hypertens. 18, 129 (2005), (Review) Abstract
Caffeine and the dopaminergic system: O. Cauli & M. Morelli; Behav. Pharmacol. 16, 63 (2005), (Review) Abstract
Immunomodulatory effects of caffeine: friend or foe: L. A. Horrigan, et al.; Pharmacol. Ther. 111, 877 (2006), (Review) Abstract
Novel neuroprotection by caffeine and adenosine A(2A) receptor antagonists in animal models of Parkinson’s disease: A. Kalda, et al.; J. Neurol. Sci. 248, 9 (2006), (Review) Abstract
The enigmatic effects of caffeine in cell cycle and cancer: A. M. & Bode and Z. Dong; Cancer Lett. 247, 26 (2007), (Review) Abstract

Further Categories Containing This Product:

Natural Products - Other Signal Transduction Pathway Modulators • Ca2+ Modulators • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Chemopreventive Agents • Neuroactive Agents Other Products • Active Substances from Fruit and Vegetables • Natural Products - Anti-inflammatory Agents • DNA Repair Other Products • Alkaloids • Other Natural Products - DNA Regulation / Transcription • Natural Products for Cell Cycle Research • Phosphodiesterases / Related Products

ALX-550-516

Revised 21-May-08

Compound A
SYNONYMS	CpdA 2-((4-Acetophenyl)-2-chloro-N-methyl)ethylammonium chloride
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Anti-inflammatory Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-550-516-M005		5 mg	40.00 USD
ALX-550-516-M025		25 mg	120.00 USD

Product Specification

FORMULA:	C₁₁H₁₄ClNO₂ . HCl
MW:	227.7 . 36.5
PURITY:	≥98% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO, 100% ethanol or water.
SHIPPING:	SHIPPED ON DRY ICE
LONG TERM STORAGE:	-80°C
USE/STABILITY:	Stock solutions in ethanol are stable for up to 1 month when stored at -80°C.
HANDLING:	Protect from moisture. After reconstitution, prepare aliquots and store at -80°C.

Product Description

Cell permeable, nonsteroidal glucocorticoid receptor modulator with high binding affinity. Exerts anti-inflammatory potential by down-modulating TNF-induced pro-inflammatory gene expression, such as IL-6 and E-selectin. Unlike dexamethasone (Prod. No. ALX-370-002) it does not enhance glucocorticoid response element (GRE)-driven gene expression or induce glucocorticoid receptor (GR) binding to GRE-dependent genes in vivo.

Product Specific Literature References

A fully dissociated compound of plant origin for inflammatory gen