BM-212
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Hodoodo CAT#: H522650

CAS#: 146204-42-4

Description: BM-212 is a potent antimycobacterial agent and MmpL3 inhibitor. BM-212 was shown to possess strong inhibitory activity against both Mycobacterium tuberculosis and some nontuberculosis mycobacteria. BM212 was inhibitory to drug-resistant mycobacteria and also exerted bactericidal activity against intracellular bacilli residing in the U937 human histiocytic lymphoma cell line.


Chemical Structure

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BM-212
CAS# 146204-42-4

Theoretical Analysis

Hodoodo Cat#: H522650
Name: BM-212
CAS#: 146204-42-4
Chemical Formula: C23H25Cl2N3
Exact Mass: 413.14
Molecular Weight: 414.374
Elemental Analysis: C, 66.67; H, 6.08; Cl, 17.11; N, 10.14

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 weeks
10mg USD 650 2 weeks
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Synonym: BM-212; BM 212; BM212.

IUPAC/Chemical Name: 1-((1,5-bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine

InChi Key: YWZIODCWLMCMMW-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H25Cl2N3/c1-17-19(16-27-13-11-26(2)12-14-27)15-23(18-3-5-20(24)6-4-18)28(17)22-9-7-21(25)8-10-22/h3-10,15H,11-14,16H2,1-2H3

SMILES Code: CN1CCN(CC2=C(C)N(C3=CC=C(Cl)C=C3)C(C4=CC=C(Cl)C=C4)=C2)CC1

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, not in water

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: BM212 is a potent Mycobacterial membrane protein Large 3 (MmpL3) inhibitor.
In vitro activity: The growth of cells expressing MmpL3V197M or MmpL3A326T variants is only fully inhibited in the presence of four- to eightfold the concentration of BM212 that inhibits wild-type growth (SI Appendix, Table S1). BM212 does not affect MmpL3 levels in wild-type spheroplasts (SI Appendix, Fig. S7); yet, it strongly inhibits TMM flipping in a dose-dependent manner (Fig. 5 A and D). Reference: Proc Natl Acad Sci U S A. 2017 Jul 25; 114(30): 7993–7998. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5544280/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.8 1.81
Ethanol 3.0 7.31

Preparing Stock Solutions

The following data is based on the product molecular weight 414.37 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: 1. Xu Z, Meshcheryakov VA, Poce G, Chng SS. MmpL3 is the flippase for mycolic acids in mycobacteria. Proc Natl Acad Sci U S A. 2017 Jul 25;114(30):7993-7998. doi: 10.1073/pnas.1700062114. Epub 2017 Jul 11. PMID: 28698380; PMCID: PMC5544280.
In vitro protocol: 1. Xu Z, Meshcheryakov VA, Poce G, Chng SS. MmpL3 is the flippase for mycolic acids in mycobacteria. Proc Natl Acad Sci U S A. 2017 Jul 25;114(30):7993-7998. doi: 10.1073/pnas.1700062114. Epub 2017 Jul 11. PMID: 28698380; PMCID: PMC5544280.
In vivo protocol: TBD

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1: Bhakta S, Scalacci N, Maitra A, Brown AK, Dasugari S, Evangelopoulos D, McHugh TD, Mortazavi PN, Twist A, Petricci E, Manetti F, Castagnolo D. Design and synthesis of 1-((1,5-bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and N-Adamantan-2-yl-N'-((E)-3,7-dimethyl-octa-2,6-dienyl)-ethane-1,2-diamine (SQ109) pyrrole hybrid derivatives: discovery of potent anti-tubercular agents effective against multi-drug resistant mycobacteria. J Med Chem. 2016 Feb 23. [Epub ahead of print] PubMed PMID: 26907951.

1: Li W, Upadhyay A, Fontes FL, North EJ, Wang Y, Crans DC, Grzegorzewicz AE, Jones V, Franzblau SG, Lee RE, Crick DC, Jackson M. Novel insights into the mechanism of inhibition of MmpL3, a target of multiple pharmacophores in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2014 Nov;58(11):6413-23. doi: 10.1128/AAC.03229-14. Epub 2014 Aug 18. PubMed PMID: 25136022; PubMed Central PMCID: PMC4249373.

2: Poce G, Bates RH, Alfonso S, Cocozza M, Porretta GC, Ballell L, Rullas J, Ortega F, De Logu A, Agus E, La Rosa V, Pasca MR, De Rossi E, Wae B, Franzblau SG, Manetti F, Botta M, Biava M. Improved BM212 MmpL3 inhibitor analogue shows efficacy in acute murine model of tuberculosis infection. PLoS One. 2013;8(2):e56980. doi: 10.1371/journal.pone.0056980. Epub 2013 Feb 21. PubMed PMID: 23437287; PubMed Central PMCID: PMC3578785.

3: La Rosa V, Poce G, Canseco JO, Buroni S, Pasca MR, Biava M, Raju RM, Porretta GC, Alfonso S, Battilocchio C, Javid B, Sorrentino F, Ioerger TR, Sacchettini JC, Manetti F, Botta M, De Logu A, Rubin EJ, De Rossi E. MmpL3 is the cellular target of the antitubercular pyrrole derivative BM212. Antimicrob Agents Chemother. 2012 Jan;56(1):324-31. doi: 10.1128/AAC.05270-11. Epub 2011 Oct 24. PubMed PMID: 22024828; PubMed Central PMCID: PMC3256021.

4: Biava M, Porretta GC, Poce G, De Logu A, Meleddu R, De Rossi E, Manetti F, Botta M. 1,5-Diaryl-2-ethyl pyrrole derivatives as antimycobacterial agents: design, synthesis, and microbiological evaluation. Eur J Med Chem. 2009 Nov;44(11):4734-8. doi: 10.1016/j.ejmech.2009.06.005. Epub 2009 Jun 13. PubMed PMID: 19595488.

5: Biava M, Porretta GC, Poce G, De Logu A, Saddi M, Meleddu R, Manetti F, De Rossi E, Botta M. 1,5-Diphenylpyrrole derivatives as antimycobacterial agents. Probing the influence on antimycobacterial activity of lipophilic substituents at the phenyl rings. J Med Chem. 2008 Jun 26;51(12):3644-8. doi: 10.1021/jm701560p. PubMed PMID: 18494459.

6: Biava M, Porretta GC, Manetti F. New derivatives of BM212: A class of antimycobacterial compounds based on the pyrrole ring as a scaffold. Mini Rev Med Chem. 2007 Jan;7(1):65-78. Review. PubMed PMID: 17266639.

7: Biava M, Porretta GC, Poce G, Supino S, Deidda D, Pompei R, Molicotti P, Manetti F, Botta M. Antimycobacterial agents. Novel diarylpyrrole derivatives of BM212 endowed with high activity toward Mycobacterium tuberculosis and low cytotoxicity. J Med Chem. 2006 Aug 10;49(16):4946-52. PubMed PMID: 16884306.

8: Biava M, Porretta GC, Deidda D, Pompei R. New trends in development of antimycobacterial compounds. Infect Disord Drug Targets. 2006 Jun;6(2):159-72. Review. PubMed PMID: 16789877.

9: Biava M, Porretta GC, Poce G, Deidda D, Pompei R, Tafi A, Manetti F. Antimycobacterial compounds. Optimization of the BM 212 structure, the lead compound for a new pyrrole derivative class. Bioorg Med Chem. 2005 Feb 15;13(4):1221-30. PubMed PMID: 15670931.

10: Biava M, Porretta GC, Deidda D, Pompei R, Tafi A, Manetti F. Antimycobacterial compounds. New pyrrole derivatives of BM212. Bioorg Med Chem. 2004 Mar 15;12(6):1453-8. PubMed PMID: 15018918.

11: Biava M, Cesare Porretta G, Deidda D, Pompei R, Tafi A, Manetti F. Importance of the thiomorpholine introduction in new pyrrole derivatives as antimycobacterial agents analogues of BM 212. Bioorg Med Chem. 2003 Feb 20;11(4):515-20. PubMed PMID: 12538016.

12: Biava M. BM 212 and its derivatives as a new class of antimycobacterial active agents. Curr Med Chem. 2002 Nov;9(21):1859-69. Review. PubMed PMID: 12369872.

13: Biava M, Fioravanti R, Porretta GC, Deidda D, Maullu C, Pompei R. New pyrrole derivatives as antimycobacterial agents analogs of BM212. Bioorg Med Chem Lett. 1999 Oct 18;9(20):2983-8. PubMed PMID: 10571160.

14: Duchêne P, Laneury JP, Tran G, Ladure P, Ollivier R, Buzas A, Merour JY, Houin G. Pharmacokinetics, metabolism and bioavailability of the new anti-allergic drug BM 113. Part III: Pharmacokinetics, metabolism, dose dependency and gender effect after single or repeated administration to human healthy volunteers. Arzneimittelforschung. 1999 Aug;49(8):699-704. PubMed PMID: 10483517.

15: Duchêne P, Tran G, Ladure P, Ollivier R, Buzas A, Merour JY, Houin G. Pharmacokinetics, metabolism and bioavailability of the new anti-allergic drug BM 113. Part I: Pharmacokinetics and tissular distribution in Sprague-Dawley rats. Arzneimittelforschung. 1999 Jun;49(6):504-8. PubMed PMID: 10417866.

16: Deidda D, Lampis G, Fioravanti R, Biava M, Porretta GC, Zanetti S, Pompei R. Bactericidal activities of the pyrrole derivative BM212 against multidrug-resistant and intramacrophagic Mycobacterium tuberculosis strains. Antimicrob Agents Chemother. 1998 Nov;42(11):3035-7. PubMed PMID: 9797251; PubMed Central PMCID: PMC105991.