INF55 | CAS#4993-87-7

MedKoo Cat#: 525207 | Name: INF55

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

INF55 is a NorA efflux pump inhibitor.

Chemical Structure

INF55

CAS#4993-87-7

Theoretical Analysis

MedKoo Cat#: 525207

Name: INF55

CAS#: 4993-87-7

Chemical Formula: C14H10N2O2

Exact Mass: 238.0742

Molecular Weight: 238.25

Elemental Analysis: Chemical Formula: C14H10N2O2 Exact Mass: 238.0742 Molecular Weight: 238.2460 Elemental Analysis: C, 70.58; H, 4.23; N, 11.76; O, 13.43

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 500.00	2 Weeks
500mg	USD 850.00	2 Weeks
1g	USD 1,450.00	2 Weeks

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Synonym

INF55; INF-55; INF 55;

IUPAC/Chemical Name

5-Nitro-2-phenyl-1H-indole

InChi Key

UNJRQDPTLDVHOR-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H10N2O2/c17-16(18)12-6-7-13-11(8-12)9-14(15-13)10-4-2-1-3-5-10/h1-9,15H

SMILES Code

O=[N+](C1=CC2=C(NC(C3=CC=CC=C3)=C2)C=C1)[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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

INF55 is a NorA efflux pump inhibitor.

In vitro activity:

This study hypothesised that if the proposed mechanism is correct, then hybrids carrying more potent INF55 pump inhibitor structures should show enhanced antibacterial effects relative to those bearing weaker inhibitors. Two INF55 analogues showing graded reductions in NorA inhibitory activity compared with INF55 were identified and their corresponding berberine-INF55 hybrids carrying equivalent INF55 inhibitor structures synthesised. Multiple assays comparing the antibacterial effects of the hybrids and their corresponding berberine-INF55 analogue combinations showed that the three hybrids all show very similar activities, leading this study to conclude that the antibacterial mechanism(s) of berberine-INF55 hybrids is different from berberine-INF55 combinations. Reference: Aust J Chem. 2015;67:1471-1480. https://pubmed.ncbi.nlm.nih.gov/26806960/

In vivo activity:

In conclusion, this study demonstrates that attaching NorA EPIs to MB can increase aPDI effectiveness against the Gram-negative pathogens E. coli and A. baumannii in vitro and in vivo. Reference: Bioorg Med Chem Lett. 2018 Sep 1;28(16):2736-2740. https://pubmed.ncbi.nlm.nih.gov/29519734/

Preparing Stock Solutions

The following data is based on the product molecular weight 238.25 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.

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. Dolla NK, Chen C, Larkins-Ford J, Rajamuthiah R, Jagadeesan S, Conery AL, Ausubel FM, Mylonakis E, Bremner JB, Lewis K, Kelso MJ. On the Mechanism of Berberine-INF55 (5-Nitro-2-phenylindole) Hybrid Antibacterials. Aust J Chem. 2015;67:1471-1480. doi: 10.1071/CH14426. PMID: 26806960; PMCID: PMC4720975. 2. Bremner JB, Kelso MJ. Synthesis of Berberine-Efflux Pump Inhibitor Hybrid Antibacterials. Synth Commun. 2010 Jan 1;40(23):3561-3568. doi: 10.1080/00397910903457415. PMID: 21311737; PMCID: PMC3035389. 3. Rineh A, Bremner JB, Hamblin MR, Ball AR, Tegos GP, Kelso MJ. Attaching NorA efflux pump inhibitors to methylene blue enhances antimicrobial photodynamic inactivation of Escherichia coli and Acinetobacter baumannii in vitro and in vivo. Bioorg Med Chem Lett. 2018 Sep 1;28(16):2736-2740. doi: 10.1016/j.bmcl.2018.02.041. Epub 2018 Feb 24. PMID: 29519734; PMCID: PMC6108959.

In vitro protocol:

In vivo protocol:

1. Rineh A, Bremner JB, Hamblin MR, Ball AR, Tegos GP, Kelso MJ. Attaching NorA efflux pump inhibitors to methylene blue enhances antimicrobial photodynamic inactivation of Escherichia coli and Acinetobacter baumannii in vitro and in vivo. Bioorg Med Chem Lett. 2018 Sep 1;28(16):2736-2740. doi: 10.1016/j.bmcl.2018.02.041. Epub 2018 Feb 24. PMID: 29519734; PMCID: PMC6108959.

1: Dolla NK, Chen C, Larkins-Ford J, Rajamuthiah R, Jagadeesan S, Conery AL, Ausubel FM, Mylonakis E, Bremner JB, Lewis K, Kelso MJ. On the Mechanism of Berberine-INF55 (5-Nitro-2-phenylindole) Hybrid Antibacterials. Aust J Chem. 2015;67:1471-1480. PubMed PMID: 26806960; PubMed Central PMCID: PMC4720975. 2: Liger F, Bouhours P, Ganem-Elbaz C, Jolivalt C, Pellet-Rostaing S, Popowycz F, Paris JM, Lemaire M. C2 Arylated Benzo[b]thiophene Derivatives as Staphylococcus aureus NorA Efflux Pump Inhibitors. ChemMedChem. 2016 Feb 4;11(3):320-30. doi: 10.1002/cmdc.201500463. Epub 2016 Jan 6. PubMed PMID: 26732895. 3: Wang S, Yu J, Suvira M, Setlow P, Li YQ. Uptake of and Resistance to the Antibiotic Berberine by Individual Dormant, Germinating and Outgrowing Bacillus Spores as Monitored by Laser Tweezers Raman Spectroscopy. PLoS One. 2015 Dec 4;10(12):e0144183. doi: 10.1371/journal.pone.0144183. eCollection 2015. PubMed PMID: 26636757; PubMed Central PMCID: PMC4670213. 4: Aygül A. [The importance of efflux systems in antibiotic resistance and efflux pump inhibitors in the management of resistance]. Mikrobiyol Bul. 2015 Apr;49(2):278-91. Review. Turkish. PubMed PMID: 26167829. 5: Bremner JB, Kelso MJ. Synthesis of Berberine-Efflux Pump Inhibitor Hybrid Antibacterials. Synth Commun. 2010 Jan 1;40(23):3561-3568. PubMed PMID: 21311737; PubMed Central PMCID: PMC3035389. 6: Tomkiewicz D, Casadei G, Larkins-Ford J, Moy TI, Garner J, Bremner JB, Ausubel FM, Lewis K, Kelso MJ. Berberine-INF55 (5-nitro-2-phenylindole) hybrid antimicrobials: effects of varying the relative orientation of the berberine and INF55 components. Antimicrob Agents Chemother. 2010 Aug;54(8):3219-24. doi: 10.1128/AAC.01715-09. Epub 2010 May 24. PubMed PMID: 20498327; PubMed Central PMCID: PMC2916310. 7: Samosorn S, Tanwirat B, Muhamad N, Casadei G, Tomkiewicz D, Lewis K, Suksamrarn A, Prammananan T, Gornall KC, Beck JL, Bremner JB. Antibacterial activity of berberine-NorA pump inhibitor hybrids with a methylene ether linking group. Bioorg Med Chem. 2009 Jun 1;17(11):3866-72. doi: 10.1016/j.bmc.2009.04.028. Epub 2009 Apr 19. PubMed PMID: 19419877; PubMed Central PMCID: PMC2759347. 8: Ambrus JI, Kelso MJ, Bremner JB, Ball AR, Casadei G, Lewis K. Structure-activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus. Bioorg Med Chem Lett. 2008 Aug 1;18(15):4294-7. doi: 10.1016/j.bmcl.2008.06.093. Epub 2008 Jul 2. PubMed PMID: 18632270; PubMed Central PMCID: PMC2590755.