MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 562205 | Name: Methylenebis
Featured

Description:

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

Methylenebis is an autophagy-regulator. It acts by sensitizing tumor cells to belotecan, a derivative of camptothecin, as a topoisomerase I inhibitor.

Chemical Structure

Methylenebis
Methylenebis
CAS#119-47-1

Theoretical Analysis

MedKoo Cat#: 562205

Name: Methylenebis

CAS#: 119-47-1

Chemical Formula: C23H32O2

Exact Mass: 340.2402

Molecular Weight: 340.51

Elemental Analysis: C, 81.13; H, 9.47; O, 9.40

Price and Availability

Size Price Availability Quantity
25g USD 250.00 2 weeks
100g USD 450.00 2 weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Methylenebis; Bisalkofen BP; Antioxidant 2246; Antioxidant-2246; Antioxidant2246; Bisalkofen-BP;
IUPAC/Chemical Name
2,2'-Methylenebis[6-tert-butyl-p-cresol]
InChi Key
KGRVJHAUYBGFFP-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H32O2/c1-14-9-16(20(24)18(11-14)22(3,4)5)13-17-10-15(2)12-19(21(17)25)23(6,7)8/h9-12,24-25H,13H2,1-8H3
SMILES Code
CC1=CC(C(C)(C)C)=C(O)C(CC2=CC(C)=CC(C(C)(C)C)=C2O)=C1
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:
Methylenebis is an autophagy-regulator.
In vitro activity:
2,2'-methylenebis (6-tert-butyl 4-methylphenol), hereafter referred to as methylenebis, is a novel autophagy-regulating small molecule that sensitizes tumor cells to belotecan, which is a derivative of camptothecin, a topoisomerase I inhibitor. Methylenebis activates autophagic flux by increasing the level of LC3-II and forming autolysosome puncta. Moreover, methylenebis enhances the antitumor efficacy of belotecan by activating both autophagy and apoptosis. Reference: Oncotarget. 2017 Dec 1;8(70):115068-115078. https://pubmed.ncbi.nlm.nih.gov/29383142/
In vivo activity:
The current work aimed to assess the possible protective effects and the mechanism of protection of 3,3'-methylenebis-(1-ethyl-4-hydroxyquinolin-2(1H)-one) on BLM-induced lung injury in addition to the effect and underlying mechanisms of nuclear factor-erythroid-related factor 2 pathway against this injury. Group IV (BLM with 1-ethyl-4-hydroxyquinolin-2(1H)-one-treated group) exhibited amelioration in the previously mentioned parameters and histological alternations that were induced by BLM. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2022 Dec 8:1–18. https://pubmed.ncbi.nlm.nih.gov/36480028/

Preparing Stock Solutions

The following data is based on the product molecular weight 340.51 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. Jang M, Kim H, Park R, Jo D, Lee EJ, Oh WK, Park J. 2,2'-Methylenebis (6-tert-butyl 4-methylphenol) enhances the antitumor efficacy of belotecan, a derivative of camptothecin, by inducing autophagy. Oncotarget. 2017 Dec 1;8(70):115068-115078. doi: 10.18632/oncotarget.22858. PMID: 29383142; PMCID: PMC5777754. 2. Insuasty B, García A, Quiroga J, Abonia R, Ortiz A, Nogueras M, Cobo J. Efficient microwave-assisted synthesis and antitumor activity of novel 4,4'-methylenebis[2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols]. Eur J Med Chem. 2011 Jun;46(6):2436-40. doi: 10.1016/j.ejmech.2011.03.028. Epub 2011 Mar 23. PMID: 21481989. 3. Hafez SMNA, Saber EA, Aziz NM, Kamel MY, Aly AA, Abdelhafez EMN, Ibrahim MFG. Potential protective effect of 3,3'-methylenebis(1-ethyl-4-hydroxyquinolin-2(1H)-one) against bleomycin-induced lung injury in male albino rat via modulation of Nrf2 pathway: biochemical, histological, and immunohistochemical study. Naunyn Schmiedebergs Arch Pharmacol. 2022 Dec 8:1–18. doi: 10.1007/s00210-022-02324-1. Epub ahead of print. PMID: 36480028; PMCID: PMC9734634. 4. Harvilchuck JA, Hong SP, Richey JS, Osheroff MR, Johnson JD. In vivo acetylcholinesterase reactivation in male guinea pigs and rhesus macaques following cyclosarin exposure and treatment with 1,1'-methylenebis{4-[(hydroxyimino)methyl] pyridinium} dimethanesulfonate. Int J Toxicol. 2013 Jul-Aug;32(4 Suppl):99S-107S. doi: 10.1177/1091581813498778. PMID: 23929454.
In vitro protocol:
1. Jang M, Kim H, Park R, Jo D, Lee EJ, Oh WK, Park J. 2,2'-Methylenebis (6-tert-butyl 4-methylphenol) enhances the antitumor efficacy of belotecan, a derivative of camptothecin, by inducing autophagy. Oncotarget. 2017 Dec 1;8(70):115068-115078. doi: 10.18632/oncotarget.22858. PMID: 29383142; PMCID: PMC5777754. 2. Insuasty B, García A, Quiroga J, Abonia R, Ortiz A, Nogueras M, Cobo J. Efficient microwave-assisted synthesis and antitumor activity of novel 4,4'-methylenebis[2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols]. Eur J Med Chem. 2011 Jun;46(6):2436-40. doi: 10.1016/j.ejmech.2011.03.028. Epub 2011 Mar 23. PMID: 21481989.
In vivo protocol:
1. Hafez SMNA, Saber EA, Aziz NM, Kamel MY, Aly AA, Abdelhafez EMN, Ibrahim MFG. Potential protective effect of 3,3'-methylenebis(1-ethyl-4-hydroxyquinolin-2(1H)-one) against bleomycin-induced lung injury in male albino rat via modulation of Nrf2 pathway: biochemical, histological, and immunohistochemical study. Naunyn Schmiedebergs Arch Pharmacol. 2022 Dec 8:1–18. doi: 10.1007/s00210-022-02324-1. Epub ahead of print. PMID: 36480028; PMCID: PMC9734634. 2. Harvilchuck JA, Hong SP, Richey JS, Osheroff MR, Johnson JD. In vivo acetylcholinesterase reactivation in male guinea pigs and rhesus macaques following cyclosarin exposure and treatment with 1,1'-methylenebis{4-[(hydroxyimino)methyl] pyridinium} dimethanesulfonate. Int J Toxicol. 2013 Jul-Aug;32(4 Suppl):99S-107S. doi: 10.1177/1091581813498778. PMID: 23929454.
1: Johari-Ahar M, Karami P, Ghanei M, Afkhami A, Bagheri H. Development of a molecularly imprinted polymer tailored on disposable screen-printed electrodes for dual detection of EGFR and VEGF using nano-liposomal amplification strategy. Biosens Bioelectron. 2018 Feb 3;107:26-33. doi: 10.1016/j.bios.2018.02.005. [Epub ahead of print] PubMed PMID: 29427883. 2: Jang M, Kim H, Park R, Jo D, Lee EJ, Oh WK, Park J. 2,2'-Methylenebis (6-tert-butyl 4-methylphenol) enhances the antitumor efficacy of belotecan, a derivative of camptothecin, by inducing autophagy. Oncotarget. 2017 Dec 1;8(70):115068-115078. doi: 10.18632/oncotarget.22858. eCollection 2017 Dec 29. PubMed PMID: 29383142; PubMed Central PMCID: PMC5777754. 3: Joshi A, Nandi S, Chester D, Brown AC, Muller M. Study of Poly(N-isopropylacrylamide-co-acrylic acid) (pNIPAM) Microgel Particle Induced Deformations of Tissue-Mimicking Phantom by Ultrasound Stimulation. Langmuir. 2018 Jan 30;34(4):1457-1465. doi: 10.1021/acs.langmuir.7b02801. Epub 2018 Jan 9. PubMed PMID: 29257896. 4: Yang X, Song W, Liu N, Sun Z, Liu R, Liu QS, Zhou Q, Jiang G. Synthetic Phenolic Antioxidants Cause Perturbation in Steroidogenesis in Vitro and in Vivo. Environ Sci Technol. 2018 Jan 16;52(2):850-858. doi: 10.1021/acs.est.7b05057. Epub 2017 Dec 28. PubMed PMID: 29236469. 5: Hein DW, Zhang X, Doll MA. Role of N-acetyltransferase 2 acetylation polymorphism in 4, 4'-methylene bis (2-chloroaniline) biotransformation. Toxicol Lett. 2018 Feb;283:100-105. doi: 10.1016/j.toxlet.2017.11.028. Epub 2017 Nov 24. PubMed PMID: 29180287; PubMed Central PMCID: PMC5745265. 6: Liu M, Gao K, Fan Y, Guo X, Wu J, Meng X, Hou H. Co-Cluster-Based Metal-Organic Frameworks as Selective Catalysts for Benzene Tandem Acylation-Nazarov Cyclization to Benzocyclopentanone. Chemistry. 2018 Jan 26;24(6):1416-1424. doi: 10.1002/chem.201704749. Epub 2017 Dec 18. PubMed PMID: 29105862. 7: Zhou T, Wang Y, Huang S, Zhao Y. Synthesis composite hydrogels from inorganic-organic hybrids based on leftover rice for environment-friendly controlled-release urea fertilizers. Sci Total Environ. 2018 Feb 15;615:422-430. doi: 10.1016/j.scitotenv.2017.09.084. Epub 2017 Oct 4. PubMed PMID: 28988078. 8: Modarresi-Saryazdi SM, Haddadi-Asl V, Salami-Kalajahi M. N,N'-methylenebis(acrylamide)-crosslinked poly(acrylic acid) particles as doxorubicin carriers: A comparison between release behavior of physically loaded drug and conjugated drug via acid-labile hydrazone linkage. J Biomed Mater Res A. 2018 Feb;106(2):342-348. doi: 10.1002/jbm.a.36240. Epub 2017 Oct 11. PubMed PMID: 28921847. 9: Guo X, Gu D, Wang M, Huang Y, Li H, Dong Y, Tian J, Wang Y, Yang Y. Characterization of active compounds from Gracilaria lemaneiformis inhibiting the protein tyrosine phosphatase 1B activity. Food Funct. 2017 Sep 20;8(9):3271-3275. doi: 10.1039/c7fo00376e. PubMed PMID: 28829084. 10: Aftim N, Istamboulié G, Piletska E, Piletsky S, Calas-Blanchard C, Noguer T. Biosensor-assisted selection of optimal parameters for designing molecularly imprinted polymers selective to phosmet insecticide. Talanta. 2017 Nov 1;174:414-419. doi: 10.1016/j.talanta.2017.06.035. Epub 2017 Jun 16. PubMed PMID: 28738601. 11: Funk P, Motyka K, Soural M, Malon M, Koshino H, Kusz J, Hlavac J. Study of 2-aminoquinolin-4(1H)-one under Mannich and retro-Mannich reaction. PLoS One. 2017 May 30;12(5):e0175364. doi: 10.1371/journal.pone.0175364. eCollection 2017. PubMed PMID: 28557987; PubMed Central PMCID: PMC5448738. 12: Kucinska-Lipka J, Gubanska I, Strankowski M, Cieśliński H, Filipowicz N, Janik H. Synthesis and characterization of cycloaliphatic hydrophilic polyurethanes, modified with l-ascorbic acid, as materials for soft tissue regeneration. Mater Sci Eng C Mater Biol Appl. 2017 Jun 1;75:671-681. doi: 10.1016/j.msec.2017.02.052. Epub 2017 Feb 16. PubMed PMID: 28415514. 13: Malik NS, Ahmad M, Minhas MU. Cross-linked β-cyclodextrin and carboxymethyl cellulose hydrogels for controlled drug delivery of acyclovir. PLoS One. 2017 Feb 28;12(2):e0172727. doi: 10.1371/journal.pone.0172727. eCollection 2017. PubMed PMID: 28245257; PubMed Central PMCID: PMC5330485. 14: Rashedul HK, Kalam MA, Masjuki HH, Teoh YH, How HG, Monirul IM, Imdadul HK. Attempts to minimize nitrogen oxide emission from diesel engine by using antioxidant-treated diesel-biodiesel blend. Environ Sci Pollut Res Int. 2017 Apr;24(10):9305-9313. doi: 10.1007/s11356-017-8573-9. Epub 2017 Feb 23. PubMed PMID: 28233198. 15: Liu X, Niu Y, Chen KC, Chen S. Rapid hemostatic and mild polyurethane-urea foam wound dressing for promoting wound healing. Mater Sci Eng C Mater Biol Appl. 2017 Feb 1;71:289-297. doi: 10.1016/j.msec.2016.10.019. Epub 2016 Oct 17. PubMed PMID: 27987710. 16: Zhu R, Wang X, Yang J, Wang Y, Zhang Z, Hou Y, Lin F. Influence of hydroxyl-terminated polydimethylsiloxane on high-strength biocompatible polycarbonate urethane films. Biomed Mater. 2016 Dec 9;12(1):015011. PubMed PMID: 27934785. 17: Heather E, Bortz A, Shimmon R, McDonagh AM. Organic impurity profiling of methylone and intermediate compounds synthesized from catechol. Drug Test Anal. 2017 Mar;9(3):436-445. doi: 10.1002/dta.2140. Epub 2017 Feb 10. PubMed PMID: 27886663. 18: Datta S, Sahdeo S, Gray JA, Morriseau C, Hammock BD, Cortopassi G. A high-throughput screen for mitochondrial function reveals known and novel mitochondrial toxicants in a library of environmental agents. Mitochondrion. 2016 Nov;31:79-83. doi: 10.1016/j.mito.2016.10.001. Epub 2016 Oct 4. PubMed PMID: 27717841; PubMed Central PMCID: PMC5108672. 19: Wang CC, Chen WL, Hsiung CN, Chiang ST, Wang YC, Loh CH, Lin IS, Chen HI, Liou SH. Effect of CYP3A4 genetic polymorphisms on the genotoxicity of 4,4'-methylene-bis(2-chloroaniline)-exposed workers. Occup Environ Med. 2017 Jan;74(1):30-38. doi: 10.1136/oemed-2016-103816. Epub 2016 Sep 27. PubMed PMID: 27679675. 20: Meller K, Pomastowski P, Szumski M, Buszewski B. Preparation of an improved hydrophilic monolith to make trypsin-immobilized microreactors. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Feb 1;1043:128-137. doi: 10.1016/j.jchromb.2016.08.032. Epub 2016 Aug 21. PubMed PMID: 27595484.