ChemicalBook CAS DataBase List 11029-61-1

11029-61-1

Name	GRAMICIDIN A
CAS	11029-61-1
EINECS(EC#)	234-259-8
Molecular Formula	C99H140N20O17
MDL Number	MFCD00466944
Molecular Weight	1882.29
MOL File	11029-61-1.mol

Synonyms

GA GLS2 GRIMICIDIN A GRAMICIDIN A GRAMICIDIN A USP/EP/BP Alphafoetoprotein, Human Gramicidin A, High Purity, GRAMICIDIN A, BACILLUS BREVIS GRAMICIDIN A FROM BACILLUS BREVIS gramicidinafrombacillusbrevis95+% GrimicidinA(HighPurity),Bacillusbrevis Glutaminase liver isoform, mitochondrial ANTI-GLS2 (C-TERM E513) antibody produced in rabbit Gramicidin A, High Purity, Bacillus brevis - CAS 11029-61-1 - Calbiochem HCO-VAL-GLY-ALA-D-LEU-ALA-D-VAL-VAL-D-VAL-TRP-D-LEU-TRP-D-LEU-TRP-D-LEU-NHCH2CH2OH HCO-VAL-GLY-ALA-D-LEU-ALA-D-VAL-VAL-D-VAL-TRP-D-LEU-TRP-D-LEU-TRP-D-LEU-TRP-NHCH2CH2OH OHC-NH-VAL-GLY-ALA-D-LEU-ALA-D-VAL-VAL-D-VAL-TRP-D-LEU-TRP-D-LEU-TRP-D-LEU-TRP-CONCH2CH2OH HCO-X-GLY-L-ALA-D-LEU-L-ALA-D-VAL-L-VAL-D-VAL-L-TRP-D-LEU-L-TRP-D-LEU-L-TRP-D-LEU-L-TRP-NHCH2CH2OH OHC-NH-VAL-GLY-ALA-D-LEU-ALA-D-VAL-VAL-D-VAL-TRP-D-LEU-TRP-D-LEU-TRP-D-LEU-TRP-D-LEU-TRP-CONHCH2CH2OH

Chemical Properties

storage temp.	2-8°C
solubility	ethanol: soluble
form	White to off-white solid
color	colorless or white
BRN	6461131
Sequence	{For}-Val-Gly-Ala-{D-Leu}-Ala-{D-Val}-Val-{D-Val}-Trp-{D-Leu}-Trp-{D-Leu}-Trp-{D-Leu}-Trp-{NHCH2CH2OH}
InChIKey	ZWCXYZRRTRDGQE-LUPIJMBPSA-N

Safety Data

Hazard Codes	Xn
Risk Statements	22 less more
WGK Germany	3
RTECS	MD8230000
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral
Toxicity	mouse,LD50,intraperitoneal,60mg/kg (60mg/kg),"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 4(1), Pg. 240, 1980. less more

Hazard Information

Uses

Gramicidin A is an effective antibiotic against Gram positive organisms.

Biological Activity

Cell permeable: no''Primary Target
Causes the formation of a monovalent cation-selective ion channel''Product does not compete with ATP.''Reversible: no

in vivo

Gramicidin A (0.11 mg/kg; intratumoral injection; twice weekly for 14 days) inhibits the growth of RCC tumor xenografts^[2].
Gramicidin A (0.22 mg/kg; intratumoral injection; thrice weekly for 26 days) inhibits the growth and angiogenesis of VHL-expressing RCC tumor xenografts^[3].

Animal Model:	Female hairless Nu/J mice, 6- to 8-week old, injected subcutaneously with a suspension of SN12C cells (1.0 × 10⁶) in a 50% growth factor–reduced Matrigel solution^[2]
Dosage:	0.11 mg/kg body weight
Administration:	Intratumoral injection, twice weekly for 14 days
Result:	The average tumor mass was reduced by approximately 40% without significant toxicity.

Animal Model:	Female hairless 6- to 8-week-old Nu/J mice, injected subcutaneously with a suspension of Caki-1-td-Tomato cells (1.5 × 10⁶) in a 50% growth factor-reduced Matrigel solution^[3].
Dosage:	0.22 mg/kg
Administration:	Intratumoral injection, thrice weekly for 26 days
Result:	Inhibited tumor growth. HIF-2α and GAPDH protein expression was substantially reduced.

Purification Methods

Purify gramicidin A by countercurrent distribution from *C6H6/CHCl3, MeOH/H2O (15:15:23:7) with 5000 tubes. Fractions are examined by UV (280nm) of small aliquots. Separation from gramicidin C and other material occurred after 999 transfers. [Gross & Witkop Biochemistry 4 2495 1965, Bauer et al. Biochemistry 11 3266 1972.] Purify it finally by recrystallisation from EtOH/H2O and dry it at 100o/10-2mm over KOH. It forms platelets m 229-230o. It is almost insoluble in H2O (0.6%) but soluble in lower alcohols, dry Me2CO, dioxane, acetic acid and pyridine. The commercial material is more difficult to crystallise than the synthetic compound. [Sarges & Witkop J Am Chem Soc 86 1861 1964, 87 2011, 2020 1965.] It has characteristic [] D20 +27.3o (c 1.3, MeOH) and UV max at 282nm ( 22,100). The N-carbamoyldeformyl gramicidine A precipitates from EtOAc/pet ether (b 40-60o). [Beilstein 26 III/IV 4273.]

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