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MedKoo Cat#: 562807 | Name: Bz-423
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Description:

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

Bz-423 is a pro-apoptotic 1,4-benzodiazepine derivative that selectively targets the F1F0-ATPase in mitochondria, disrupting cellular energy metabolism. By inhibiting ATP synthesis and inducing oxidative stress, it promotes apoptosis in pathogenic immune cells while sparing normal cells. This mechanism has been investigated for potential therapeutic applications in autoimmune diseases, leukemia, and other hyperproliferative disorders.

Chemical Structure

Bz-423
Bz-423
CAS#216691-95-1

Theoretical Analysis

MedKoo Cat#: 562807

Name: Bz-423

CAS#: 216691-95-1

Chemical Formula: C27H21ClN2O2

Exact Mass: 440.1292

Molecular Weight: 440.92

Elemental Analysis: C, 73.55; H, 4.80; Cl, 8.04; N, 6.35; O, 7.26

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Bz-423; Bz 423; Bz423;
IUPAC/Chemical Name
7-Chloro-1,3-dihydro-5-(4-hydroxyphenyl)-1-methyl-3-(2-naphthalenylmethyl)-2H-1,4-benzodiazepin-2-one
InChi Key
HIJCSNHREFFOML-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H21ClN2O2/c1-30-25-13-10-21(28)16-23(25)26(19-8-11-22(31)12-9-19)29-24(27(30)32)15-17-6-7-18-4-2-3-5-20(18)14-17/h2-14,16,24,31H,15H2,1H3
SMILES Code
O=C1N(C)C2=CC=C(Cl)C=C2C(C3=CC=C(O)C=C3)=NC1CC4=CC=C5C=CC=CC5=C4
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

Preparing Stock Solutions

The following data is based on the product molecular weight 440.92 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
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PMID: 36260776. 4: Sambri I, Massa F, Gullo F, Meneghini S, Cassina L, Carraro M, Dina G, Quattrini A, Patanella L, Carissimo A, Iuliano A, Santorelli F, Codazzi F, Grohovaz F, Bernardi P, Becchetti A, Casari G. Impaired flickering of the permeability transition pore causes SPG7 spastic paraplegia. EBioMedicine. 2020 Nov;61:103050. doi: 10.1016/j.ebiom.2020.103050. Epub 2020 Oct 9. PMID: 33045469; PMCID: PMC7553352. 5: Hearne A, Chen H, Monarchino A, Wiseman JS. Oligomycin-induced proton uncoupling. Toxicol In Vitro. 2020 Sep;67:104907. doi: 10.1016/j.tiv.2020.104907. Epub 2020 Jun 2. PMID: 32502624. 6: Starke I, Glick GD, Börsch M. Visualizing Mitochondrial FoF1-ATP Synthase as the Target of the Immunomodulatory Drug Bz-423. Front Physiol. 2018 Jul 4;9:803. doi: 10.3389/fphys.2018.00803. PMID: 30022951; PMCID: PMC6039829. 7: Witkin JM, Cerne R, Wakulchik M, S J, Gleason SD, Jones TM, Li G, Arnold LA, Li JX, Schkeryantz JM, Methuku KR, Cook JM, Poe MM. Further evaluation of the potential anxiolytic activity of imidazo[1,5-a][1,4]diazepin agents selective for α2/3-containing GABAA receptors. Pharmacol Biochem Behav. 2017 Jun;157:35-40. doi: 10.1016/j.pbb.2017.04.009. Epub 2017 Apr 22. PMID: 28442369; PMCID: PMC5519285. 8: Ettari R, Previti S, Cosconati S, Maiorana S, Schirmeister T, Grasso S, Zappalà M. Development of novel 1,4-benzodiazepine-based Michael acceptors as antitrypanosomal agents. Bioorg Med Chem Lett. 2016 Aug 1;26(15):3453-6. doi: 10.1016/j.bmcl.2016.06.047. Epub 2016 Jun 21. PMID: 27372809. 9: Livingstone E, Swann S, Lilla C, Schadendorf D, Roesch A. Combining BRAF(V) (600E) inhibition with modulators of the mitochondrial bioenergy metabolism to overcome drug resistance in metastatic melanoma. Exp Dermatol. 2015 Sep;24(9):709-10. doi: 10.1111/exd.12718. Epub 2015 May 8. PMID: 25865258. 10: von Stockum S, Giorgio V, Trevisan E, Lippe G, Glick GD, Forte MA, Da-Rè C, Checchetto V, Mazzotta G, Costa R, Szabò I, Bernardi P. F-ATPase of Drosophila melanogaster forms 53-picosiemen (53-pS) channels responsible for mitochondrial Ca2+-induced Ca2+ release. J Biol Chem. 2015 Feb 20;290(8):4537-4544. doi: 10.1074/jbc.C114.629766. Epub 2014 Dec 30. PMID: 25550160; PMCID: PMC4335195. 11: Holovenko MIa, Larionov VB. [Kinetics of hydrolysis of 1,4-benzodiazepine derivative by carboxylesterases in mice organism]. Ukr Biochem J. 2014 Jul- Aug;86(4):150-7. Ukrainian. doi: 10.15407/ubj86.04.150. PMID: 25509194. 12: Giorgio V, von Stockum S, Antoniel M, Fabbro A, Fogolari F, Forte M, Glick GD, Petronilli V, Zoratti M, Szabó I, Lippe G, Bernardi P. Dimers of mitochondrial ATP synthase form the permeability transition pore. Proc Natl Acad Sci U S A. 2013 Apr 9;110(15):5887-92. doi: 10.1073/pnas.1217823110. Epub 2013 Mar 25. PMID: 23530243; PMCID: PMC3625323. 13: Che C, Li S, Yu Z, Li F, Xin S, Zhou L, Lin S, Yang Z. One-pot syntheses of isoquinolin-3-ones and benzo-1,4-diazepin-2,5-diones utilizing Ugi-4CR post- transformation strategy. ACS Comb Sci. 2013 Apr 8;15(4):202-7. doi: 10.1021/co400001h. Epub 2013 Mar 7. PMID: 23441930. 14: Huang Y, Khoury K, Chanas T, Dömling A. Multicomponent synthesis of diverse 1,4-benzodiazepine scaffolds. Org Lett. 2012 Dec 7;14(23):5916-9. doi: 10.1021/ol302837h. Epub 2012 Nov 16. PMID: 23157402; PMCID: PMC3732779. 15: Zhong W, Yang X, Tong W, Martin GE. Structural characterization of a novel degradant of the antifungal agent posaconazole. J Pharm Biomed Anal. 2012 Jul;66:40-9. doi: 10.1016/j.jpba.2012.02.023. Epub 2012 Mar 10. PMID: 22464557. 16: Cellai C, Balliu M, Laurenzana A, Guandalini L, Matucci R, Miniati D, Torre E, Nebbioso A, Carafa V, Altucci L, Romanelli MN, Paoletti F. The new low-toxic histone deacetylase inhibitor S-(2) induces apoptosis in various acute myeloid leukaemia cells. J Cell Mol Med. 2012 Aug;16(8):1758-65. doi: 10.1111/j.1582-4934.2011.01464.x. Erratum in: J Cell Mol Med. 2024 Nov;28(21):e70001. doi: 10.1111/jcmm.70001. PMID: 22004558; PMCID: PMC3822689. 17: Wang F, Li Y, Ma Z, Wang X, Wang Y. Structural determinants of benzodiazepinedione/peptide-based p53-HDM2 inhibitors using 3D-QSAR, docking and molecular dynamics. J Mol Model. 2012 Jan;18(1):295-306. doi: 10.1007/s00894-011-1041-4. Epub 2011 Apr 27. PMID: 21523548. 18: Donald JR, Martin SF. Synthesis and diversification of 1,2,3-triazole-fused 1,4-benzodiazepine scaffolds. Org Lett. 2011 Mar 4;13(5):852-5. doi: 10.1021/ol1028404. Epub 2011 Jan 28. PMID: 21275426; PMCID: PMC3045640. 19: Gatza E, Wahl DR, Opipari AW, Sundberg TB, Reddy P, Liu C, Glick GD, Ferrara JL. Manipulating the bioenergetics of alloreactive T cells causes their selective apoptosis and arrests graft-versus-host disease. Sci Transl Med. 2011 Jan 26;3(67):67ra8. doi: 10.1126/scitranslmed.3001975. PMID: 21270339; PMCID: PMC3364290. 20: Stelzer AC, Frazee RW, Van Huis C, Cleary J, Opipari AW Jr, Glick GD, Al- Hashimi HM. NMR studies of an immunomodulatory benzodiazepine binding to its molecular target on the mitochondrial F(1)F(0)-ATPase. Biopolymers. 2010 Jan;93(1):85-92. doi: 10.1002/bip.21306. PMID: 19768783.