Bohemine - CAS 189232-42-6
Catalog number:
189232-42-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C18H24N6O
Molecular Weight:
340.42
COA:
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Targets:
CDK
Description:
Bohemine, structurally similar to Olomoucine and Roscovitine, is a 2,6,9-trisubstituted purine derivative that inhibits cyclin-dependent kinases (CDKs) and exhibits anticancer activity.
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Purity:
≥97%
Appearance:
Solid powder
Synonyms:
3-[[6-(benzylamino)-9-propan-2-ylpurin-2-yl]amino]propan-1-ol; 6-benzylamino-2-(3-hydroxypropylamino)-9-isopropylpurine; bohemine
MSDS:
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InChIKey:
OPQGFIAVPSXOBO-UHFFFAOYSA-N
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)
Canonical SMILES:
CC(C)N1C=NC2=C1N=C(N=C2NCC3=CC=CC=C3)NCCCO
1.Conformation and recognition of DNA damaged by antitumor cis-dichlorido platinum(II) complex of CDK inhibitor bohemine.
Novakova O1, Liskova B1, Vystrcilova J1, Suchankova T1, Vrana O1, Starha P2, Travnicek Z2, Brabec V3. Eur J Med Chem. 2014 May 6;78:54-64. doi: 10.1016/j.ejmech.2014.03.041. Epub 2014 Mar 15.
A substitution of the ammine ligands of cisplatin, cis-[Pt(NH3)2Cl2], for cyclin dependent kinase (CDK) inhibitor bohemine (boh), [2-(3-hydroxypropylamino)-6-benzylamino-9-isopropylpurine], results in a compound, cis-[Pt(boh)2Cl2] (C1), with the unique anticancer profile which may be associated with some features of the damaged DNA and/or its cellular processing (Travnicek Z et al. (2003) J Inorg Biochem94, 307-316; Liskova B (2012) Chem Res Toxicol25, 500-509). A combination of biochemical and molecular biology techniques was used to establish mechanistic differences between cisplatin and C1 with respect to the DNA damage they produce and their interactions with critical DNA-binding proteins, DNA-processing enzymes and glutathione. The results show that replacement of the NH3 groups in cisplatin by bohemine modulates some aspects of the mechanism of action of C1. More specifically, the results of the present work are consistent with the thesis that, in comparison with cisplatin, effects of other factors, such as: (i) slower rate of initial binding of C1 to DNA; (ii) the lower efficiency of C1 to form bifunctional adducts; (iii) the reduced bend of longitudinal DNA axis induced by the major 1,2-GG intrastrand cross-link of C1; (iv) the reduced affinity of HMG domain proteins to the major adduct of C1; (v) the enhanced efficiency of the DNA adducts of C1 to block DNA polymerization and to inhibit transcription activity of human RNA pol II and RNA transcription; (vi) slower rate of the reaction of C1 with glutathione, may partially contribute to the unique activity of C1.
2.Cellular response to antitumor cis-Dichlorido platinum(II) complexes of CDK inhibitor Bohemine and its analogues.
Liskova B1, Zerzankova L, Novakova O, Kostrhunova H, Travnicek Z, Brabec V. Chem Res Toxicol. 2012 Feb 20;25(2):500-9. doi: 10.1021/tx200525n. Epub 2012 Feb 1.
The cellular and molecular pharmacology of the new class of anticancer drugs, in which the CDK inhibitor bohemine and its analogues are coordinated to Pt(II) to form cisplatin derivatives, was investigated. The results revealed the unique anticancer profile of a cisplatin-derived platinum(II) dichlorido complex involving N(7)-coordinated bohemine (C1). Although the IC(50) values were ∼6-fold higher for C1 than for cisplatin in cisplatin-sensitive tumor cells, the tumor cells in which C1 was also active are those which acquired resistance to cisplatin. In addition, among the novel conjugates of bohemine and its analogues with cisplatin, marked selectivity of C1 for tumor cells relative to the nontumorigenic, normal cells was observed. However, coordination of bohemine to platinum in C1 considerably reduced one of the dual functionalities anticipated to be effective after C1 reaches the nucleus. Further studies performed in the cells with wt p53 status show differences between cisplatin and C1 at the level of cell cycle regulation.
3.Diverse effects of the cyclin-dependent kinase inhibitor bohemine: Concentration- and time-dependent suppression or stimulation of hybridoma culture.
Franek F1, Strnad M, Havlícek L, Siglerová V, Fismolová I, Eckschlager T. Cytotechnology. 2001 Jul;36(1-3):117-23. doi: 10.1023/A:1014020415912.
An analog of aromatic cytokinins, the 2,6,9-trisubstituted purine derivative bohemine, was applied to cultures of mouse hybridoma cells in order to analyze its capacity of suppressing cell growth and maintaining or enhancing the production of monoclonal antibody. Addition of bohemine at concentrations in the range of1-10 muM resulted in a short-term arrest of growth and of monoclonal antibody production. The short-term suppression of cell functions was followed by a significant temporary increase of specific growth rate and of specific production rate. The steady-state viable cell density values, found in semicontinuous cultures, showed a certain stimulation of cell growth in the range of micromolar concentrations of bohemine, and inhibition of growth at 10 and 30 muM concentrations. The profiles of cell cycle phases indicated that hybridoma cells are retarded both at the G(1)/S boundary and at the G(2)/M boundary, depending on bohemine concentration.
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CAS 189232-42-6 Bohemine

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