Bohemine | CAS#189232-42-6 | CDK inhibitor

MedKoo Cat#: 407146 | Name: Bohemine

Description:

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

Bohemine is a potent and selective, cell-permeable, cyclin-dependent kinase (CDK) inhibitor with IC50 = 1 µM. Bohemine is structurally similar to Olomoucine and Roscovitine.

Chemical Structure

Bohemine

CAS#189232-42-6

Theoretical Analysis

MedKoo Cat#: 407146

Name: Bohemine

CAS#: 189232-42-6

Chemical Formula: C18H24N6O

Exact Mass: 340.2012

Molecular Weight: 340.43

Elemental Analysis: C, 63.51; H, 7.11; N, 24.69; O, 4.70

Price and Availability

Size	Price	Availability
25mg	USD 285.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 850.00	2 Weeks
250mg	USD 1,650.00	2 Weeks

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Related CAS #

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Synonym

Bohemine

IUPAC/Chemical Name

3-((6-(benzylamino)-9-isopropyl-9H-purin-2-yl)amino)propan-1-ol

InChi Key

OPQGFIAVPSXOBO-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H24N6O/c1-13(2)24-12-21-15-16(20-11-14-7-4-3-5-8-14)22-18(23-17(15)24)19-9-6-10-25/h3-5,7-8,12-13,25H,6,9-11H2,1-2H3,(H2,19,20,22,23)

SMILES Code

CC(N1C=NC2=C1N=C(NCCCO)N=C2NCC3=CC=CC=C3)C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 340.43 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

1: Liskova B, Zerzankova L, Novakova O, Kostrhunova H, Travnicek Z, Brabec V. Cellular response to antitumor cis-Dichlorido platinum(II) complexes of CDK inhibitor Bohemine and its analogues. Chem Res Toxicol. 2012 Feb 20;25(2):500-9. doi: 10.1021/tx200525n. Epub 2012 Feb 1. PMID: 22250642. 2: Novakova O, Liskova B, Vystrcilova J, Suchankova T, Vrana O, Starha P, Travnicek Z, Brabec V. Conformation and recognition of DNA damaged by antitumor cis-dichlorido platinum(II) complex of CDK inhibitor bohemine. Eur J Med Chem. 2014 May 6;78:54-64. doi: 10.1016/j.ejmech.2014.03.041. Epub 2014 Mar 15. PMID: 24675180. 3: Alberio R, Kubelka M, Zakhartchenko V, Hajdúch M, Wolf E, Motlik J. Activation of bovine oocytes by specific inhibition of cyclin-dependent kinases. Mol Reprod Dev. 2000 Apr;55(4):422-32. doi: 10.1002/(SICI)1098-2795(200004)55:4<422::AID-MRD10>3.0.CO;2-C. PMID: 10694750. 4: Raynaud FI, Whittaker SR, Fischer PM, McClue S, Walton MI, Barrie SE, Garrett MD, Rogers P, Clarke SJ, Kelland LR, Valenti M, Brunton L, Eccles S, Lane DP, Workman P. In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202. Clin Cancer Res. 2005 Jul 1;11(13):4875-87. doi: 10.1158/1078-0432.CCR-04-2264. PMID: 16000586. 5: Bogoeva VP, Varriale A, John CM, D'Auria S. Human galectin-3 interacts with two anticancer drugs. Proteomics. 2010 May;10(10):1946-53. doi: 10.1002/pmic.200900581. Erratum in: Proteomics. 2010 Jul;110(13):2560. PMID: 20209510. 6: Chmela Z, Veselý J, Lemr K, Rypka M, Hanus J, Havlícek L, Krystof V, Michnová L, Fuksová K, Lukes J. In vivo metabolism of 2,6,9-trisubstituted purine-derived cyclin-dependent kinase inhibitor bohemine in mice: glucosidation as the principal metabolic route. Drug Metab Dispos. 2001 Mar;29(3):326-34. PMID: 11181503. 7: Korinkova G, Cwiertka K, Paprskarova M, Dzubak P, Hajduch M. The radiosensitising effect of olomoucine derived synthetic cyclin-dependent kinase inhibitors. Neoplasma. 2010;57(2):161-9. doi: 10.4149/neo_2010_02_161. PMID: 20099981. 8: Trávnícek Z, Malon M, Zatloukal M, Dolezal K, Strnad M, Marek J. Mixed ligand complexes of platinum(II) and palladium(II) with cytokinin-derived compounds Bohemine and Olomoucine: X-ray structure of [Pt(BohH+-N7)Cl(3)].9/5H2O [Boh=6-(benzylamino)-2-[(3-(hydroxypropyl)-amino]-9-isopropylpurine, Bohemine]. J Inorg Biochem. 2003 Apr 1;94(4):307-16. doi: 10.1016/s0162-0134(03)00051-5. PMID: 12667701. 9: Skalnikova H, Halada P, Dzubak P, Hajduch M, Kovarova H. Protein fingerprints of anti-cancer effects of cyclin-dependent kinase inhibition: identification of candidate biomarkers using 2-D liquid phase separation coupled to mass spectrometry. Technol Cancer Res Treat. 2005 Aug;4(4):447-54. doi: 10.1177/153303460500400412. PMID: 16029063. 10: Franek F, Strnad M, Havlícek L, Siglerová V, Fismolová I, Eckschlager T. Diverse effects of the cyclin-dependent kinase inhibitor bohemine: Concentration- and time-dependent suppression or stimulation of hybridoma culture. Cytotechnology. 2001 Jul;36(1-3):117-23. doi: 10.1023/A:1014020415912. PMID: 19003322; PMCID: PMC3449669. 11: Kovárová H, Hajdúch M, Korínková G, Halada P, Krupicková S, Gouldsworthy A, Zhelev N, Strnad M. Proteomics approach in classifying the biochemical basis of the anticancer activity of the new olomoucine-derived synthetic cyclin-dependent kinase inhibitor, bohemine. Electrophoresis. 2000 Nov;21(17):3757-64. doi: 10.1002/1522-2683(200011)21:17<3757::AID-ELPS3757>3.0.CO;2-X. PMID: 11271495. 12: Kovarova H, Halada P, Man P, Dzubak P, Hajduch M. Application of proteomics in the search for novel proteins associated with the anti-cancer effect of the synthetic cyclin-dependent kinases inhibitor, bohemine. Technol Cancer Res Treat. 2002 Aug;1(4):247-56. doi: 10.1177/153303460200100405. PMID: 12625783. 13: Mad'arová J, Lukesová M, Hlobilková A, Strnad M, Vojtesek B, Lenobel R, Hajdúch M, Murray PG, Perera S, Kolár Z. Synthetic inhibitors of CDKs induce different responses in androgen sensitive and androgen insensitive prostatic cancer cell lines. Mol Pathol. 2002 Aug;55(4):227-34. doi: 10.1136/mp.55.4.227. PMID: 12147712; PMCID: PMC1187184. 14: Rypka M, Veselý J, Chmela Z, Riegrová D, Cervenková K, Havlícek L, Lemr K, Hanus J, Cerný B, Lukes J, Michalíková K. In vitro biotransformation of 2,6,9-trisubstituted purine-derived cyclin-dependent kinase inhibitor bohemine by mouse liver microsomes. Xenobiotica. 2002 Nov;32(11):1017-31. doi: 10.1080/0049825021000012600. PMID: 12487731. 15: Motlik J, Alberio R, Zakhartchenko V, Stojkovic M, Kubelka M, Wolf E. The effect of activation of Mammalian oocytes on remodeling of donor nuclei after nuclear transfer. Cloning Stem Cells. 2002;4(3):245-52. doi: 10.1089/15362300260339520. PMID: 12398805. 16: Pospísilová H, Sebela M, Novák O, Frébort I. Hydrolytic cleavage of N6-substituted adenine derivatives by eukaryotic adenine and adenosine deaminases. Biosci Rep. 2008 Dec;28(6):335-47. doi: 10.1042/BSR20080081. PMID: 18673302. 17: Brix DM, Rafn B, Bundgaard Clemmensen K, Andersen SH, Ambartsumian N, Jäättelä M, Kallunki T. Screening and identification of small molecule inhibitors of ErbB2-induced invasion. Mol Oncol. 2014 Dec;8(8):1703-18. doi: 10.1016/j.molonc.2014.07.004. Epub 2014 Jul 12. PMID: 25070180; PMCID: PMC5528609. 18: Alberio R, Brero A, Motlík J, Cremer T, Wolf E, Zakhartchenko V. Remodeling of donor nuclei, DNA-synthesis, and ploidy of bovine cumulus cell nuclear transfer embryos: effect of activation protocol. Mol Reprod Dev. 2001 Aug;59(4):371-9. doi: 10.1002/mrd.1043. PMID: 11468773. 19: An R, Hagiya Y, Tamura A, Li S, Saito H, Tokushima D, Ishikawa T. Cellular phototoxicity evoked through the inhibition of human ABC transporter ABCG2 by cyclin-dependent kinase inhibitors in vitro. Pharm Res. 2009 Feb;26(2):449-58. doi: 10.1007/s11095-008-9738-5. Epub 2008 Oct 9. PMID: 18841444. 20: Cervenková K, Belejová M, Chmela Z, Rypka M, Riegrová D, Michnová K, Michalíková K, Súrová I, Brejcha A, Hanus J, Cerný B, Fuksová K, Havlícek L, Veselý J. In vitro glycosidation potential towards olomoucine-type cyclin- dependent kinase inhibitors in rodent and primate microsomes. Physiol Res. 2003;52(4):467-74. PMID: 12899660.

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