Boromycin

Structural formula
General
Surname	Boromycin
other names	[1 - {(1 R ) -1 - [(1 R , 2 R , 5 S , 6 R , 8 R , 12 R , 14 S , 17 R , 18 R , 22 S , 24 Z , 28 S , 30 S , 33 R ) -12,28-dihydroxy-1,2,18,19-tetra (hydroxy-κO) -6,13,13,17,29,29,33-heptamethyl-3,20-dioxo-4 , 7,21,34,35-pentaoxatetracyclo [28.3.1.1 5,8 .1 14,18 ] hexatriacont-24-en-22-yl] ethoxy} -3-methyl-1-oxo-2-butanaminiumato (4− )] boron ( IUPAC )
Molecular formula	C 45 H 74 BNO 15
Brief description	odorless solid
External identifiers / databases
PubChem	6436027
ChemSpider	16735705
Wikidata	Q4946240
properties
Molar mass	879.88 g mol −1
Physical state	firmly
Melting point	223–228 ° C (decomposition)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: 264-270-301 + 312-330-501
Toxicological data	180 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Boromycin is a bacteriocidal macrocyclic antibiotic that contains a borate complex in the center. Chemically, it is the D- valine ester of a Böeseken complex of boric acid with a macrodiolide . It was originally isolated from the Streptomyces strain Streptomyces antibioticus in 1967 and was the first organic natural product containing boron. The antibiotic effect exists against gram-positive , but not against gram-negative bacteria . It also inhibits the development of certain types of fungi and protozoa . Boromycin kills bacteria by affecting their cell membrane in such a way that the cell loses potassium , which ultimately leads to cell death .

Boromycin has shown strong inhibitory effects on the replication of HIV- 1 strains in laboratory studies . The mechanism of action seems to involve an interaction with later stages of HIV infection . In in vitro studies showed boromycin as a strong inhibitor of mycobacteria with a MIC ₅₀ of 80 n M against Mycobacterium tuberculosis .

Extraction and presentation

The total synthesis of the macrodiolide ionophore boromycin can take place via double ring contraction.

Individual evidence

↑ ^a ^b ^c SCBT: MSDS Boromycin (CAS 34524-20-4) , accessed May 14, 2020.
↑ ^a ^b ^c W. Kliegel: Boron in biology, medicine and pharmacy: Physiological effects and application of boron compounds . Springer-Verlag, 2013, ISBN 978-3-662-11266-3 , pp. 391 ( books.google.de ).
↑ Wilfried Moreira, Dinah B. Aziz, Thomas Dick: Boromycin Kills Mycobacterial Persisters without Detectable Resistance . In: Frontiers in Microbiology . tape 7 , 2016, doi : 10.3389 / fmicb.2016.00199 .
↑ JD Dunitz, DM Hawley, D. Mikloš, DNJ White, Yu Berlin, R. Marušić, V. Prelog: Structure of boromycin . In: Helvetica Chimica Acta . tape 54 , no. 6 , 1971, p. 1709–1713 , doi : 10.1002 / hlca.19710540624 .
↑ R. Hütter, W. Keller ‐ Schien, F. Knüsel, V. Prelog, GC Rodgers, P. Suter, G. Vogel, W. Voser, H. Zahner: Metabolic products of microorganisms. Part 57. Boromycin . In: Helvetica Chimica Acta . tape 50 , no. 6 , 1967, p. 1533–1539 , doi : 10.1002 / hlca.19670500612 .
↑ J. Kohno, T. Kawahata, T. Otake et al .: Boromycin, an anti-HIV Antibiotic . Ed .: Bioscience, Biotechnology and Biochemistry. tape 60 (1996) , pp. 1036-1037 , doi : 10.1271 / bbb.60.1036 .
↑ W. Moreira, DB Aziz, T. Dick: Boromycin Kills Mycobacterial Persisters without Detectable Resistance . In: Frontiers in Microbiology . tape 7 (2016) , pp. 199 , doi : 10.3389 / fmicb.2016.00199 .
↑ Mitchell A. Avery, Satish C. Choudhry, Om Prakash Dhingra, Brian D. Gray, Myung-chol Kang, Shen-chun Kuo, Thalathani R. Vedananda, James D. White, Alan J. Whittle: Total synthesis of macrodiolide ionophores aplasmomycin A and boromycin via double ring contraction . In: Organic & Biomolecular Chemistry . tape 12 , no. 45 , 2014, p. 9116-9132 , doi : 10.1039 / c4ob01017e , PMID 25096282 .
↑ John ApSimon: The Total Synthesis of Natural Products . John Wiley & Sons, 2009, ISBN 978-0-470-12953-1 , pp. 296 ( books.google.de ).

[SCBT-1] SCBT: MSDS Boromycin (CAS 34524-20-4) , accessed May 14, 2020.

[Kliegel-2] W. Kliegel: Boron in biology, medicine and pharmacy: Physiological effects and application of boron compounds . Springer-Verlag, 2013, ISBN 978-3-662-11266-3 , pp. 391 ( books.google.de ).

[3] Wilfried Moreira, Dinah B. Aziz, Thomas Dick: Boromycin Kills Mycobacterial Persisters without Detectable Resistance . In: Frontiers in Microbiology . tape 7 , 2016, doi : 10.3389 / fmicb.2016.00199 .

[4] JD Dunitz, DM Hawley, D. Mikloš, DNJ White, Yu Berlin, R. Marušić, V. Prelog: Structure of boromycin . In: Helvetica Chimica Acta . tape 54 , no. 6 , 1971, p. 1709–1713 , doi : 10.1002 / hlca.19710540624 .

[5] R. Hütter, W. Keller ‐ Schien, F. Knüsel, V. Prelog, GC Rodgers, P. Suter, G. Vogel, W. Voser, H. Zahner: Metabolic products of microorganisms. Part 57. Boromycin . In: Helvetica Chimica Acta . tape 50 , no. 6 , 1967, p. 1533–1539 , doi : 10.1002 / hlca.19670500612 .

[6] J. Kohno, T. Kawahata, T. Otake et al .: Boromycin, an anti-HIV Antibiotic . Ed .: Bioscience, Biotechnology and Biochemistry. tape 60 (1996) , pp. 1036-1037 , doi : 10.1271 / bbb.60.1036 .

[7] W. Moreira, DB Aziz, T. Dick: Boromycin Kills Mycobacterial Persisters without Detectable Resistance . In: Frontiers in Microbiology . tape 7 (2016) , pp. 199 , doi : 10.3389 / fmicb.2016.00199 .

[8] Mitchell A. Avery, Satish C. Choudhry, Om Prakash Dhingra, Brian D. Gray, Myung-chol Kang, Shen-chun Kuo, Thalathani R. Vedananda, James D. White, Alan J. Whittle: Total synthesis of macrodiolide ionophores aplasmomycin A and boromycin via double ring contraction . In: Organic & Biomolecular Chemistry . tape 12 , no. 45 , 2014, p. 9116-9132 , doi : 10.1039 / c4ob01017e , PMID 25096282 .

[9] John ApSimon: The Total Synthesis of Natural Products . John Wiley & Sons, 2009, ISBN 978-0-470-12953-1 , pp. 296 ( books.google.de ).