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MedKoo Cat#: 584816 | Name: Pravibismane
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Description:

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

Pravibismane, also known as BisEDT, MBN 101, is a novel broad-spectrum topical anti-infective and an antibacterial agent against a broad range of gram-positive and gram-negative pathogens. Pravibismane inhibited adherence of P. aeruginosa to 16HBE14o- cells by 28% and to a collagen matrix by 53%. Pravibismane-treated bacteria were also 100-fold more sensitive to serum bactericidal activity.

Chemical Structure

Pravibismane
Pravibismane
CAS#175880-68-9

Theoretical Analysis

MedKoo Cat#: 584816

Name: Pravibismane

CAS#: 175880-68-9

Chemical Formula: C6H12Bi2S6

Exact Mass: 693.8871

Molecular Weight: 694.48

Elemental Analysis: C, 10.38; H, 1.74; Bi, 60.18; S, 27.70

Price and Availability

Size Price Availability Quantity
5mg USD 90.00 Ready to ship
10mg USD 160.00 Ready to ship
25mg USD 350.00 Ready to ship
50mg USD 550.00 Ready to ship
100mg USD 950.00 Ready to ship
200mg USD 1,650.00 Ready to ship
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Related CAS #
No Data
Synonym
Pravibismane; BisEDT; MBN 101; MBN-101; MBN101; Bismuth ethanedithiol;
IUPAC/Chemical Name
2,2'-[ethane-1,2-diylbis(sulfanediyl)]bis(1,3,2-dithiabismolane)
InChi Key
GUTNLKRPYCTIHX-UHFFFAOYSA-H
InChi Code
InChI=1S/3C2H6S2.2Bi/c3*3-1-2-4;;/h3*3-4H,1-2H2;;/q;;;2*+3/p-6
SMILES Code
[Bi]1(SCCS[Bi]2SCCS2)SCCS1
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
>3 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
Certificate of Analysis
View CoA: current batch, Lot#S21S08C30
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Antibacterial agent against a broad range of gram-positive and gram-negative pathogens.
In vitro activity:
B. multivorans and B. cenocepacia showed a wide range of susceptibilities to BTs. Bismuth ethanedithiol (BisEDT) was one of the more potent BTs against these organisms (MIC50 7.8 microM), and was selected for synergy studies. Selected strains were highly resistant to tobramycin. The addition of subinhibitory concentrations of BisEDT (2 microM) reduced the MIC and MBC of tobramycin against all strains, achieving synergy in many instances. The FIC index was in the range 0.28-0.66 and the FBC in the range 0.12-0.85. Most strains became susceptible to tobramycin at clinically achievable concentrations in the presence of non-toxic BisEDT levels. Reference: Veloira WG, Domenico P, LiPuma JJ, Davis JM, Gurzenda E, Kazzaz JA. In vitro activity and synergy of bismuth thiols and tobramycin against Burkholderia cepacia complex. J Antimicrob Chemother. 2003 Dec;52(6):915-9. doi: 10.1093/jac/dkg471. Epub 2003 Oct 29. PMID: 14585856.
In vivo activity:
The quorum-sensing signal molecule N-acyl homoserine lactone was monitored by using a biosensor organism. P. aeruginosa virulence factors were assessed spectrophotometrically. An agar beads model of chronic Pseudomonas lung infection in rats was used to evaluate the efficacy of the liposomal formulation in the reduction of bacterial count. The levels of active tobramycin in the lungs and the kidneys were evaluated by microbiological assay. LipoBiEDT-TOB was effective in disrupting both quorum-sensing signal molecules N-3-oxo-dodeccanoylhomoserine lactone and N-butanoylhomoserine lactone, as well as significantly (P < 0.05) reducing lipase, chitinase, and protease production. At 24 h after 3 treatments, the CFU counts in lungs of animals treated with LipoBiEDT-TOB were of 3 log(10) CFU/lung, comparated to 7.4 and 4.7 log(10) CFU/lung, respectively, in untreated lungs and in lungs treated with free antibiotic. The antibiotic concentration after the last dose of LipoBiEDT-TOB was 25.1 μg/lung, while no tobramycin was detected in the kidneys. As for the free antibiotic, we found 6.5 μg/kidney but could not detect any tobramycin in the lungs. Taken together, LipoBiEDT-TOB reduced the production of quorum-sensing molecules and virulence factors and could highly improve the management of chronic pulmonary infection in cystic fibrosis patients. Reference: Alhariri M, Omri A. Efficacy of liposomal bismuth-ethanedithiol-loaded tobramycin after intratracheal administration in rats with pulmonary Pseudomonas aeruginosa infection. Antimicrob Agents Chemother. 2013 Jan;57(1):569-78. doi: 10.1128/AAC.01634-12. Epub 2012 Nov 12. PMID: 23147741; PMCID: PMC3535983.

Preparing Stock Solutions

The following data is based on the product molecular weight 694.48 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:
Veloira WG, Domenico P, LiPuma JJ, Davis JM, Gurzenda E, Kazzaz JA. In vitro activity and synergy of bismuth thiols and tobramycin against Burkholderia cepacia complex. J Antimicrob Chemother. 2003 Dec;52(6):915-9. doi: 10.1093/jac/dkg471. Epub 2003 Oct 29. PMID: 14585856.
In vitro protocol:
Veloira WG, Domenico P, LiPuma JJ, Davis JM, Gurzenda E, Kazzaz JA. In vitro activity and synergy of bismuth thiols and tobramycin against Burkholderia cepacia complex. J Antimicrob Chemother. 2003 Dec;52(6):915-9. doi: 10.1093/jac/dkg471. Epub 2003 Oct 29. PMID: 14585856.
In vivo protocol:
Alhariri M, Omri A. Efficacy of liposomal bismuth-ethanedithiol-loaded tobramycin after intratracheal administration in rats with pulmonary Pseudomonas aeruginosa infection. Antimicrob Agents Chemother. 2013 Jan;57(1):569-78. doi: 10.1128/AAC.01634-12. Epub 2012 Nov 12. PMID: 23147741; PMCID: PMC3535983.
1: Domenico P, Gurzenda E, Giacometti A, Cirioni O, Ghiselli R, Orlando F, Korem M, Saba V, Scalise G, Balaban N. BisEDT and RIP act in synergy to prevent graft infections by resistant staphylococci. Peptides. 2004 Dec;25(12):2047-53. doi: 10.1016/j.peptides.2004.08.005. PMID: 15572191. 2: Jang D, Choi M, Chen J, Lee C. Enantioselective Total Synthesis of (+)-Garsubellin A. Angew Chem Int Ed Engl. 2021 Oct 11;60(42):22735-22739. doi: 10.1002/anie.202109193. Epub 2021 Sep 9. PMID: 34398517; PMCID: PMC8519110. 3: Wu CL, Domenico P, Hassett DJ, Beveridge TJ, Hauser AR, Kazzaz JA. Subinhibitory bismuth-thiols reduce virulence of Pseudomonas aeruginosa. Am J Respir Cell Mol Biol. 2002 Jun;26(6):731-8. doi: 10.1165/ajrcmb.26.6.2001-00020oc. PMID: 12034573. 4: Shu C, Zhang N, Gao Y, An J, Wen X, Ma W, Liu Z, Sun B, Li S. Multifunctional Sensors Based on Doped Indium Oxide Nanocrystals. ACS Appl Mater Interfaces. 2022 Jun 1;14(21):24648-24658. doi: 10.1021/acsami.2c05280. Epub 2022 May 17. PMID: 35581001. 5: Veloira WG, Domenico P, LiPuma JJ, Davis JM, Gurzenda E, Kazzaz JA. In vitro activity and synergy of bismuth thiols and tobramycin against Burkholderia cepacia complex. J Antimicrob Chemother. 2003 Dec;52(6):915-9. doi: 10.1093/jac/dkg471. Epub 2003 Oct 29. PMID: 14585856. 6: Wang R, Wu X, Xu K, Zhou W, Shang Y, Tang H, Chen H, Ning Z. Highly Efficient Inverted Structural Quantum Dot Solar Cells. Adv Mater. 2018 Feb;30(7). doi: 10.1002/adma.201704882. Epub 2018 Jan 8. PMID: 29315851. 7: Maier A, Strauß F, Kohlschreiber P, Schedel C, Braun K, Scheele M. Sub- nanosecond Intrinsic Response Time of PbS Nanocrystal IR-Photodetectors. Nano Lett. 2022 Apr 13;22(7):2809-2816. doi: 10.1021/acs.nanolett.1c04938. Epub 2022 Mar 21. PMID: 35311295. 8: Heredia-Moya J, Kirk KL. An improved synthesis of arsenic-biotin conjugates. Bioorg Med Chem. 2008 May 15;16(10):5743-6. doi: 10.1016/j.bmc.2008.03.054. Epub 2008 Mar 27. PMID: 18396406; PMCID: PMC2474666. 9: Kwak DH, Ramasamy P, Lee YS, Jeong MH, Lee JS. High-Performance Hybrid InP QDs/Black Phosphorus Photodetector. ACS Appl Mater Interfaces. 2019 Aug 14;11(32):29041-29046. doi: 10.1021/acsami.9b07910. Epub 2019 Jul 31. PMID: 31322342. 10: Wang Y, Hu H, Yuan M, Xia H, Zhang X, Liu J, Yang J, Xu S, Shi Z, He J, Zhang J, Gao L, Tang J, Lan X. Colloidal PbS Quantum Dot Photodiode Imager with Suppressed Dark Current. ACS Appl Mater Interfaces. 2023 Dec 20;15(50):58573-58582. doi: 10.1021/acsami.3c12918. Epub 2023 Dec 7. PMID: 38059485. 11: Takayanagi T, Miyake K, Seto M, Mizuguchi H, Okabe H, Matsuda N. Conjugation monitoring of gold nanoparticles with alkanedithiols by capillary zone electrophoresis. Anal Sci. 2023 Jul;39(7):1033-1039. doi: 10.1007/s44211-023-00299-4. Epub 2023 Feb 21. PMID: 36811184. 12: Disotuar MM, Smith JA, Li J, Alam S, Lin NP, Chou DH. Facile synthesis of insulin fusion derivatives through sortase A ligation. Acta Pharm Sin B. 2021 Sep;11(9):2719-2725. doi: 10.1016/j.apsb.2020.11.011. Epub 2020 Nov 21. PMID: 34589392; PMCID: PMC8463260. 13: Imamura R, Oto K, Kataoka K, Takasu A. Synthesis and Biodegradability of Tartaric Acid-Based Poly(ester-thioether)s via Thiol-Ene Click Polymerization. ACS Omega. 2023 Apr 12;8(26):23358-23364. doi: 10.1021/acsomega.2c07627. PMID: 37426220; PMCID: PMC10324057. 14: Lee JE, Park KH, Kim JC, Wi TU, Ha AR, Song YB, Oh DY, Woo J, Kweon SH, Yeom SJ, Cho W, Kim K, Lee HW, Kwak SK, Jung YS. Universal Solution Synthesis of Sulfide Solid Electrolytes Using Alkahest for All-Solid-State Batteries. Adv Mater. 2022 Apr;34(16):e2200083. doi: 10.1002/adma.202200083. Epub 2022 Mar 13. PMID: 35196412. 15: Gong W, Yang Y, Li Y, Guo H, Niu X. Enhanced Carrier Dynamics of CsPbBr3 Nanocrystals Enabled by Short-Ligand Ethanedithiol for Efficient Photoelectrocatalytic Photoanodes. ACS Appl Mater Interfaces. 2023 Nov 3. doi: 10.1021/acsami.3c07073. Epub ahead of print. PMID: 37922330. 16: Nguyen HT, Ryu SY, Duong AT, Lee S. Effects of 1,2-ethanedithiol concentration on performance improvement of quantum-dot LEDs. RSC Adv. 2019 Nov 25;9(66):38464-38468. doi: 10.1039/c9ra08411h. PMID: 35540207; PMCID: PMC9075991. 17: Zhu T, Zheng L, Yao X, Liu L, Huang F, Cao Y, Gong X. Ultrasensitive Solution-Processed Broadband PbSe Photodetectors through Photomultiplication Effect. ACS Appl Mater Interfaces. 2019 Mar 6;11(9):9205-9212. doi: 10.1021/acsami.8b21966. Epub 2019 Feb 19. PMID: 30720266. 18: Wang H, Xu X, Chen R, Zhao J, Cui L, Sheng G, Shi Q, Wong SC, Yin J. Bioinspired Antioxidant Defense System Constructed by Antioxidants-Eluting Electrospun F127-Based Fibers. ACS Appl Mater Interfaces. 2017 Nov 8;9(44):38313-38322. doi: 10.1021/acsami.7b12395. Epub 2017 Oct 30. PMID: 29039918. 19: Yang Y, Rao Z, Xu Q, Liang Y, Yang L. Improving the photovoltaic performance for PbS QD thin film solar cells through interface engineering. J Colloid Interface Sci. 2022 Dec;627:562-568. doi: 10.1016/j.jcis.2022.07.064. Epub 2022 Jul 14. PMID: 35870408. 20: Lipsky BA, Kim PJ, Murphy B, McKernan PA, Armstrong DG, Baker BHJ. Topical pravibismane as adjunctive therapy for moderate or severe diabetic foot infections: A phase 1b randomized, multicenter, double-blind, placebo-controlled trial. Int Wound J. 2024 Apr;21(4):e14817. doi: 10.1111/iwj.14817. PMID: 38567778; PMCID: PMC10988878.