Antimycins

The antimycins are a group of several closely related antibiotics from streptomycetes . As antimycin A refers to a mixture of different antimycins, the main components of the antimycins A ₁ , A ₂ , A ₃ and A ₄ are.

The antimycins act as an inhibitor of the respiratory chain .

Extraction and presentation

Antimycin A can be extracted from Streptomyces antibioticus cultures which are cultivated with an initial pH of 6.8 to 7.1, without iron supplementation and with 2 g DL - tryptophan . The individual representatives can be isolated by HPLC .

Representative

Antimycins

Surname	Antimycin A 1	Antimycin A 2	Antimycin A 3	Antimycin A 4
Structural formula
IUPAC name	[(2 R , 3 S , 6 S , 7 R , 8 R ) -3 - [(3-Formamido-2-hydroxybenzoyl) amino] -8-hexyl-2,6-dimethyl-4,9-dioxo-1 , 5-dioxonan-7-yl] -3-methylbutanoate	[3 - [(3-Formamido-2-hydroxybenzoyl) amino] -8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] butanoate	[(2 R , 3 S , 6 S , 7 R , 8 R ) -8-butyl-3 - [(3-formamido-2-hydroxybenzoyl) amino] -2,6-dimethyl-4,9-dioxo-1 , 5-dioxonan-7-yl] -3-methylbutanoate	[8-Butyl-3 - [(3-formamido-2-hydroxybenzoyl) amino] -2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] butanoate
German name	3-methylbutanoic acid 3 - ((3- (formylamino) -2-hydroxybenzoyl) amino) -8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester
synonym	Fintrol		Blastmycin
CAS number	642-15-9	27220-57-1	522-70-3	27220-59-3
	1397-94-0
PubChem	12550	3084471	245869	3084472
Molecular formula	C 28 H 40 N 2 O 9	C 27 H 38 N 2 O 9	C 27 H 38 N 2 O 9	C 25 H 34 N 2 O 9
Molar mass	548.63 g mol −1	534.61 g mol −1	520.58 g mol −1	506.55 g mol −1
Melting point	149-150 ° C		174-175 ° C

Properties and effects

safety instructions
Surname	Antimycin A
CAS number	1397-94-0
GHS labeling of hazardous substances danger H and P phrases H: 300-400 P: 264-273-301 + 310
Toxicological data	2.9 mg kg −1 ( LD 50 ,  duck ,  oral ) 1.8 mg · kg -1 ( LD 50 ,  guinea pigs ,  oral ) 55 mg kg −1 ( LD 50 ,  mouse ,  oral ) 28 mg kg −1 ( LD 50 ,  rat ,  oral )

The antimycins form colorless crystals that are almost insoluble in water but soluble in ethanol , acetone and diethyl ether .

Antimycin A binds to the Q _i site in the cytochrome bc ₁ complex and thus prevents electron transfer from heme b _H to ubiquinone .

It binds to complex III and thus blocks the transfer of electrons from coenzyme Q to cytochrome c . The components of the respiratory chain that lie in front of the site of action of antimycin A in complex III remain reduced. All components behind it remain oxidized. Thus, the consumption of is oxygen in the complex IV and the synthesis of ATP in the complex V inhibited.

Individual evidence

1. ^ N. Neft, TM Farley: Conditions Influencing Antimycin Production by a Streptomyces Species Grown in Chemically Defined Medium . In: Antimicrobial Agents and Chemotherapy . tape 1 , no. 3 , March 1, 1972, p. 274 , doi : 10.1128 / aac.1.3.274 (English, PDF ).
2. ↑ Steven TK Ha, Charles L. Wilkins, Sharon L. Abidi: Analysis of antimycin A by reversed-phase liquid chromatography / nuclear magnetic resonance spectrometry . In: Analytical Chemistry . tape 61 , no. 5 , March 1989, pp. 404-408 , doi : 10.1021 / ac00180a005 .
3. ↑ ^{a b} Entry on Antimycin A in the GESTIS substance database of the IFA , accessed on February 6, 2017(JavaScript required) .
4. ↑ ^{a b c d} C. Vézina: Antimycin A, a teleocidal antibiotic. In: Antimicrobial Agents and Chemotherapy . Volume 6, 1966, pp. 757-766, PMID 5985309 .
5. ↑ ^{a b c} Entry on Antimycins. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.