Diazaborine

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MedKoo CAT#: 329608

CAS#: 22959-81-5

Description: Diazaborine, also known as SA 84474, is a chemical compound that inhibits maturation of rRNAs for the large ribosomal subunit. Diazaborine blocks ribosome biogenesis by inhibiting the AAA-ATPase Drg1. Diazaborine treatment causes, within minutes, a rapid redistribution of the protein from the nucleolus to the periphery of the nucleus, which provides a possible explanation for the effect of diazaborine on rRNA processing.

Chemical Structure

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Diazaborine
CAS# 22959-81-5
Instruction

Theoretical Analysis

MedKoo Cat#: 329608
Name: Diazaborine
CAS#: 22959-81-5
Chemical Formula: C14H13BN2O3S
Exact Mass: 300.07
Molecular Weight: 300.139
Elemental Analysis: C, 56.03; H, 4.37; B, 3.60; N, 9.33; O, 15.99; S, 10.68

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Diazaborine; Diazaborine compound 2b18; Pkf 84.474; Pkf-84474; Pkf 84474; SA-84474; SA84474; SA 84474.

IUPAC/Chemical Name: 1-Hydroxy-2-(4-methylphenyl)sulfonyl-2,3,1-benzodiazaborinine

InChi Key: UQIDNSKBUXCODH-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H13BN2O3S/c1-11-6-8-13(9-7-11)21(19,20)17-15(18)14-5-3-2-4-12(14)10-16-17/h2-10,18H,1H3

SMILES Code: O=S(N1B(O)C2=CC=CC=C2C=N1)(C3=CC=C(C)C=C3)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 300.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bandyopadhyay A, Cambray S, Gao J. Fast Diazaborine Formation of Semicarbazide Enables Facile Labeling of Bacterial Pathogens. J Am Chem Soc. 2017 Jan 18;139(2):871-878. doi: 10.1021/jacs.6b11115. PubMed PMID: 27992180.

2: Ward MS, Silva I, Martinez W, Jefferson J, Rahman S, Garcia JM, Kanichar D, Roppiyakuda L, Kosmowska E, Faust MA, Tran KP, Chow F, Buglo E, Zhou F, Groziak MP, Xu HH. Identification of cellular targets of a series of boron heterocycles using TIPA II-A sensitive target identification platform. Bioorg Med Chem. 2016 Aug 1;24(15):3267-75. doi: 10.1016/j.bmc.2016.05.058. PubMed PMID: 27301675; PubMed Central PMCID: PMC4992540.

3: Jordan CA, Sandoval BA, Serobyan MV, Gilling DH, Groziak MP, Xu HH, Vey JL. Crystallographic insights into the structure-activity relationships of diazaborine enoyl-ACP reductase inhibitors. Acta Crystallogr F Struct Biol Commun. 2015 Dec;71(Pt 12):1521-30. doi: 10.1107/S2053230X15022098. PubMed PMID: 26625295; PubMed Central PMCID: PMC4666481.

4: Kim EJ, Lee JK. Effect of changes in the composition of cellular fatty acids on membrane fluidity of Rhodobacter sphaeroides. J Microbiol Biotechnol. 2015 Feb;25(2):162-73. PubMed PMID: 25418478.

5: Kanichar D, Roppiyakuda L, Kosmowska E, Faust MA, Tran KP, Chow F, Buglo E, Groziak MP, Sarina EA, Olmstead MM, Silva I, Xu HH. Synthesis, characterization, and antibacterial activity of structurally complex 2-acylated 2,3,1-benzodiazaborines and related compounds. Chem Biodivers. 2014 Sep;11(9):1381-97. doi: 10.1002/cbdv.201400007. PubMed PMID: 25238079.

6: Silva I, Real LJ, Ward MS, Xu HH. A disk-diffusion-based target identification platform for antibacterials (TIPA): an inducible assay for profiling MOAs of antibacterial compounds. Appl Microbiol Biotechnol. 2014 Jun;98(12):5551-66. doi: 10.1007/s00253-014-5623-9. PubMed PMID: 24622888.

7: Loibl M, Klein I, Prattes M, Schmidt C, Kappel L, Zisser G, Gungl A, Krieger E, Pertschy B, Bergler H. The drug diazaborine blocks ribosome biogenesis by inhibiting the AAA-ATPase Drg1. J Biol Chem. 2014 Feb 14;289(7):3913-22. doi: 10.1074/jbc.M113.536110. PubMed PMID: 24371142; PubMed Central PMCID: PMC3924260.

8: Pertschy B, Saveanu C, Zisser G, Lebreton A, Tengg M, Jacquier A, Liebminger E, Nobis B, Kappel L, van der Klei I, Högenauer G, Fromont-Racine M, Bergler H. Cytoplasmic recycling of 60S preribosomal factors depends on the AAA protein Drg1. Mol Cell Biol. 2007 Oct;27(19):6581-92. PubMed PMID: 17646390; PubMed Central PMCID: PMC2099225.

9: Pertschy B, Zisser G, Schein H, Köffel R, Rauch G, Grillitsch K, Morgenstern C, Durchschlag M, Högenauer G, Bergler H. Diazaborine treatment of yeast cells inhibits maturation of the 60S ribosomal subunit. Mol Cell Biol. 2004 Jul;24(14):6476-87. PubMed PMID: 15226447; PubMed Central PMCID: PMC434233.

10: Wehrschütz-Sigl E, Jungwirth H, Bergler H, Högenauer G. The transporters Pdr5p and Snq2p mediate diazaborine resistance and are under the control of the gain-of-function allele PDR1-12. Eur J Biochem. 2004 Mar;271(6):1145-52. PubMed PMID: 15009193.

11: Johnson-Restrepo B, Pacheco-Londoño L, Olivero-Verbel J. Molecular parameters responsible for the melting point of 1,2,3-diazaborine compounds. J Chem Inf Comput Sci. 2003 Sep-Oct;43(5):1513-9. PubMed PMID: 14502485.

12: Kremer L, Dover LG, Morbidoni HR, Vilchèze C, Maughan WN, Baulard A, Tu SC, Honoré N, Deretic V, Sacchettini JC, Locht C, Jacobs WR Jr, Besra GS. Inhibition of InhA activity, but not KasA activity, induces formation of a KasA-containing complex in mycobacteria. J Biol Chem. 2003 Jun 6;278(23):20547-54. PubMed PMID: 12654922.

13: Gilbert P, Allison DG, McBain AJ. Biofilms in vitro and in vivo: do singular mechanisms imply cross-resistance? Symp Ser Soc Appl Microbiol. 2002;(31):98S-110S. Review. PubMed PMID: 12481835.

14: Lee IH, Kim EJ, Cho YH, Lee JK. Characterization of a novel enoyl-acyl carrier protein reductase of diazaborine-resistant Rhodobacter sphaeroides mutant. Biochem Biophys Res Commun. 2002 Dec 13;299(4):621-7. PubMed PMID: 12459184.

15: Gilbert P, Allison DG, McBain AJ. Biofilms in vitro and in vivo: do singular mechanisms imply cross-resistance? J Appl Microbiol. 2002;92 Suppl:98S-110S. Review. PubMed PMID: 12000619.

16: Levy CW, Baldock C, Wallace AJ, Sedelnikova S, Viner RC, Clough JM, Stuitje AR, Slabas AR, Rice DW, Rafferty JB. A study of the structure-activity relationship for diazaborine inhibition of Escherichia coli enoyl-ACP reductase. J Mol Biol. 2001 May 25;309(1):171-80. PubMed PMID: 11491286.

17: Jungwirth H, Bergler H, Högenauer G. Diazaborine treatment of Baker's yeast results in stabilization of aberrant mRNAs. J Biol Chem. 2001 Sep 28;276(39):36419-24. PubMed PMID: 11477081.

18: Jungwirth H, Wendler F, Platzer B, Bergler H, Högenauer G. Diazaborine resistance in yeast involves the efflux pumps Ycf1p and Flr1p and is enhanced by a gain-of-function allele of gene YAP1. Eur J Biochem. 2000 Aug;267(15):4809-16. PubMed PMID: 10903515.

19: Roujeinikova A, Levy CW, Rowsell S, Sedelnikova S, Baker PJ, Minshull CA, Mistry A, Colls JG, Camble R, Stuitje AR, Slabas AR, Rafferty JB, Pauptit RA, Viner R, Rice DW. Crystallographic analysis of triclosan bound to enoyl reductase. J Mol Biol. 1999 Nov 26;294(2):527-35. PubMed PMID: 10610777.

20: Roujeinikova A, Sedelnikova S, de Boer GJ, Stuitje AR, Slabas AR, Rafferty JB, Rice DW. Inhibitor binding studies on enoyl reductase reveal conformational changes related to substrate recognition. J Biol Chem. 1999 Oct 22;274(43):30811-7. PubMed PMID: 10521472.