CAS 20449-79-0|Melittin

Introduction：Basic information about CAS 20449-79-0|Melittin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Melittin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles59
8. Synonyms

Common Name	Melittin
CAS Number	20449-79-0	Molecular Weight	2846.463
Density	1.4±0.1 g/cm3	Boiling Point	/
Molecular Formula	C₁₃₁H₂₂₉N₃₉O₃₁	Melting Point	/
MSDS	ChineseUSA	Flash Point	/
Symbol	GHS06	Signal Word	Danger

Names

Name	melittin
Synonym	More Synonyms

Melittin BiologicalActivity

Description	Melittin is a PLA2 activator, stimulates the activity of the low molecular weight PLA2, while it does not the increase activity of the high molecular weight PLA2.
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>PhospholipaseResearch Areas >>Inflammation/ImmunologyPeptidesResearch Areas >>Cancer
Target	PLA2[1]
In Vitro	Melittin, an immunologically related PLA2 stimulating peptide from bee venom, increases the activity of the high molecular weight enzyme[1]. Melittin is a cytotoxic peptide from bee venom. Melittin exhibits toxicity against both A2780CR and A2780 cells, with IC50 values of 4.5 and 6.8 μg/mL, respectively. Melittin has natural anti-bacterial, anti-viral, and anti-inflammatory properties. It has also been shown to have diverse anticancer effects in several different cancer cell lines including those of gastric, breast, ovarian, liver, prostate, cervical, and lung origins. The mechanisms by which Melittin, an amphipathic haemolytic peptide, exerts its potential anticancer effects include inhibition of cell proliferation, induction of apoptosis, and direct necrosis. Melittin can also prevent EGF-induced cell invasion through its inhibition of the PI3K/Akt/mTOR signaling pathway, but this is primarily related to breast cancer cells[2].
Cell Assay	Melittin is purified from bee venom by reversed phase liquid chromatography and reconstituted in sterile water to form a stock solution of 1 mg/mL before storage at -20 °C until required for analysis. Cell viability is assessed by an Alamar Blue (AB) cell viability reagent. Both A2780 and A2780CR cells are seeded at 1×104 cells/well in 96-well plates and incubated at 37 °C and 5% CO2 in a humidified atmosphere for 24 h. After this incubation period, the cells are treated with various concentrations of Melittin ranging from 0.5 to 14 µg/mL in 100 μL of medium, and re-incubated at 37 °C and 5% CO2 for a further 24 h. Triton X at 1% (v/v) and cell culture media are used as positive and negative controls, respectively. After this, AB is added at a final concentration of 10% (v/v) and the resultant mixture is incubated for a further 4 h at 37 °C and 5% CO2. Then, the plates are read at an excitation wavelength of 560 nm and the emission at 590 nm is recorded on a SpectraMax M3 microplate reader . Background-corrected fluorescence readings are converted to cell viability data for each test well by expressing them as percentages relative to the mean negative control value[2].
References	[1]. Steiner MR, et al. Responses of purified phospholipases A2 to phospholipase A2 activating protein (PLAP) and Melittin. Biochim Biophys Acta. 1993 Feb 10;1166(1):124-30. [2]. Alonezi S, et al. Metabolomic Profiling of the Effects of Melittin on Cisplatin Resistant and Cisplatin Sensitive Ovarian Cancer Cells Using Mass Spectrometry and Biolog Microarray Technology. Metabolites. 2016 Oct 13;6(4). pii: E35.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Molecular Formula	C₁₃₁H₂₂₉N₃₉O₃₁
Molecular Weight	2846.463
Exact Mass	2844.754150
PSA	1152.34000
LogP	-1.32
Index of Refraction	1.635
InChIKey	VDXZNPDIRNWWCW-JFTDCZMZSA-N
SMILES	CCC(C)C(NC(=O)CN)C(=O)NCC(=O)NC(C)C(=O)NC(C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(C(=O)NC(CO)C(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCC(N)=O)C(=O)NC(CCC(N)=O)C(N)=O)C(C)CC)C(C)CC)C(C)O)C(C)O)C(C)C)C(C)C
Storage condition	2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OS3965000

CHEMICAL NAME :: Melittin (honeybee)

CAS REGISTRY NUMBER :: 20449-79-0

LAST UPDATED :: 199707

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C131-H229-N39-O31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17700 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,367,1974

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,367,1974

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,367,1974

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7040 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,367,1974

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 2750 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,367,1974

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301 + H311 + H331
Precautionary Statements	P261-P280-P301 + P310-P311
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	T: Toxic;
Risk Phrases	R23/24/25
Safety Phrases	36-45-36/37/39
RIDADR	UN 3462 6.1/PG 1
WGK Germany	3
RTECS	OS3965000
HS Code	2934999090

Customs

HS Code	2934999090
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Synonyms

Glycyl-L-isoleucylglycyl-L-alanyl-L-valyl-L-leucyl-L-lysyl-L-valyl-L-leucyl-L-threonyl-L-threonylglycyl-L-leucyl-L-prolyl-L-alanyl-L-leucyl-L-isoleucyl-L-seryl-L-tryptophyl-L-isoleucyl-L-lysyl-L-arginyl-L-lysyl-L-arginyl-L-glutaminyl-L-glutamamide

EINECS 253-417-7

Melittin

L-Glutamamide, glycyl-L-isoleucylglycyl-L-alanyl-L-valyl-L-leucyl-L-lysyl-L-valyl-L-leucyl-L-threonyl-L-threonylglycyl-L-leucyl-L-prolyl-L-alanyl-L-leucyl-L-isoleucyl-L-seryl-L-tryptophyl-L-isoleucyl-L-lysyl-L-arginyl-L-lysyl-L-arginyl-L-glutaminyl-

MFCD00076868

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