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MedKoo Cat#: 319517 | Name: Bimolane
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Description:

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

Bimolane is a topoisomerase II inhibitor. Bimolane has been widely used in China as an anti-neoplastic agent and for the treatment of psoriasis. Bimolane is also a leukemogenic agent and is thought to exert its effects through the inhibition of topoisomerase II. The results of enzyme and DNA titration assays indicate that inhibition of topoisomerase II by bimolane occurred through interactions with DNA, similar to the mechanism seen with the epipodophyllotoxin-type inhibitors. These results provide evidence that bimolane is an inhibitor of topoisomerase II in vitro.

Chemical Structure

Bimolane
Bimolane
CAS#74550-97-3

Theoretical Analysis

MedKoo Cat#: 319517

Name: Bimolane

CAS#: 74550-97-3

Chemical Formula: C20H32N6O6

Exact Mass: 452.2383

Molecular Weight: 452.51

Elemental Analysis: C, 53.09; H, 7.13; N, 18.57; O, 21.21

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 1,950.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 4,850.00 2 Weeks
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Related CAS #
No Data
Synonym
AT-1727; AT1727; AT 1727; CCRIS 7574; CCRIS7574; CCRIS-7574; NSC 351358; Bimolane.
IUPAC/Chemical Name
1-(morpholin-4-ylmethyl)-4-[2-[4-(morpholin-4-ylmethyl)-3,5-dioxopiperazin-1-yl]ethyl]piperazine-2,6-dione
InChi Key
JGQGCJKPBAYEHO-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H32N6O6/c27-17-11-23(12-18(28)25(17)15-21-3-7-31-8-4-21)1-2-24-13-19(29)26(20(30)14-24)16-22-5-9-32-10-6-22/h1-16H2
SMILES Code
O=C(CN(CCN1CC(N(CN2CCOCC2)C(C1)=O)=O)C3)N(CN4CCOCC4)C3=O
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Bimolane is a topoisomerase II inhibitor.
In vitro activity:
Immunochemical staining with the CREST antibody indicated that bimolane induces micronuclei (MN) originating primarily from chromosome breakage. Interestingly fluorescence in situ hybridization (FISH) with differentially labeled chromosomes 1 and 9 centromeric probes indicated that bimolane also caused non-disjunction and polyploidy. Consistent with this, an expedited analysis of Giemsa-stained metaphase chromosomes in bimolane-treated lymphocytes revealed a high frequency of polyploidy/hyperdiploidy as well as dicentric chromosomes, and premature centromeric division (PCD). In addition, bimolane was also found to produce binucleated cells, possibly through an interference with normal functioning of intermediate filaments. Reference: Mutat Res. 2011 Dec 24;726(2):181-7. https://pubmed.ncbi.nlm.nih.gov/21944901/
In vivo activity:
The animal model of psoriasis was effectively treated by bimolane, both systemically and topically, and also by parenteral methotrexate and topical betamethasone valerate. Reference: J Dermatol. 1991 Dec;18(12):707-13. https://pubmed.ncbi.nlm.nih.gov/1806601/

Preparing Stock Solutions

The following data is based on the product molecular weight 452.51 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. Roy SK, Eastmond DA. Bimolane induces multiple types of chromosomal aberrations in human lymphocytes in vitro. Mutat Res. 2011 Dec 24;726(2):181-7. doi: 10.1016/j.mrgentox.2011.09.006. Epub 2011 Sep 16. PMID: 21944901. 2. Frantz CE, Smith H, Eades DM, Grosovsky AJ, Eastmond DA. Bimolane: in vitro inhibitor of human topoisomerase II. Cancer Lett. 1997 Dec 9;120(2):135-40. doi: 10.1016/s0304-3835(97)00303-0. PMID: 9461029. 3. Xu B, Noah PW, Skinner RB Jr, Bale G, Chesney TM, Rosenberg EW. Efficacy of bimolane in the Malassezia ovalis model of psoriasis. J Dermatol. 1991 Dec;18(12):707-13. doi: 10.1111/j.1346-8138.1991.tb03161.x. PMID: 1806601.
In vitro protocol:
1. Roy SK, Eastmond DA. Bimolane induces multiple types of chromosomal aberrations in human lymphocytes in vitro. Mutat Res. 2011 Dec 24;726(2):181-7. doi: 10.1016/j.mrgentox.2011.09.006. Epub 2011 Sep 16. PMID: 21944901. 2. Frantz CE, Smith H, Eades DM, Grosovsky AJ, Eastmond DA. Bimolane: in vitro inhibitor of human topoisomerase II. Cancer Lett. 1997 Dec 9;120(2):135-40. doi: 10.1016/s0304-3835(97)00303-0. PMID: 9461029.
In vivo protocol:
1. Xu B, Noah PW, Skinner RB Jr, Bale G, Chesney TM, Rosenberg EW. Efficacy of bimolane in the Malassezia ovalis model of psoriasis. J Dermatol. 1991 Dec;18(12):707-13. doi: 10.1111/j.1346-8138.1991.tb03161.x. PMID: 1806601.
1: Vuong MC, Hasegawa LS, Eastmond DA. A comparative study of the cytotoxic and genotoxic effects of ICRF-154 and bimolane, two catalytic inhibitors of topoisomerase II. Mutat Res. 2013 Jan 20;750(1-2):63-71. doi: 10.1016/j.mrgentox.2012.09.005. Epub 2012 Sep 21. PubMed PMID: 23000430. 2: Roy SK, Eastmond DA. Bimolane induces multiple types of chromosomal aberrations in human lymphocytes in vitro. Mutat Res. 2011 Dec 24;726(2):181-7. doi: 10.1016/j.mrgentox.2011.09.006. Epub 2011 Sep 16. PubMed PMID: 21944901. 3: Frantz CE, Smith H, Eades DM, Grosovsky AJ, Eastmond DA. Bimolane: in vitro inhibitor of human topoisomerase II. Cancer Lett. 1997 Dec 9;120(2):135-40. PubMed PMID: 9461029. 4: Xue Y, Guo Y, Xie X. Translocation t(7;11)(P15;P15) in a patient with therapy-related acute myeloid leukemia following bimolane and ICRF-154 treatment for psoriasis. Leuk Res. 1997 Feb;21(2):107-9. PubMed PMID: 9112426. 5: Chen SQ, Xue KX, Wu JZ, Ma GJ. [Mutagenic effects of bimolane]. Zhongguo Yao Li Xue Bao. 1995 Nov;16(6):531-3. Chinese. PubMed PMID: 8732050. 6: Xue KX, Ma GJ, Wu JZ. [Effects of bimolane on cell cycle cytokinesis in human lymphocytes in vitro]. Zhongguo Yao Li Xue Bao. 1994 Jan;15(1):87-9. Chinese. PubMed PMID: 8010096. 7: Zhang MH, Wang XY, Gao LS. [140 cases of acute leukemia caused by bimolane]. Zhonghua Nei Ke Za Zhi. 1993 Oct;32(10):668-72. Chinese. PubMed PMID: 8156836. 8: Xue Y, Lu D, Guo Y, Lin B. Specific chromosomal translocations and therapy-related leukemia induced by bimolane therapy for psoriasis. Leuk Res. 1992 Nov;16(11):1113-23. PubMed PMID: 1434747. 9: Xu B, Noah PW, Skinner RB Jr, Bale G, Chesney TM, Rosenberg EW. Efficacy of bimolane in the Malassezia ovalis model of psoriasis. J Dermatol. 1991 Dec;18(12):707-13. PubMed PMID: 1806601. 10: Chen LJ, Wang MY, Liu MZ. [Reproductive toxicity of bimolane in mice and rabbits]. Zhongguo Yao Li Xue Bao. 1989 Nov;10(6):557-60. Chinese. PubMed PMID: 2641857. 11: Dan N, Zhang TM. [Effects of bimolane on immune responses in mice]. Zhongguo Yao Li Xue Bao. 1988 Sep;9(5):471-4. Chinese. PubMed PMID: 3064552. 12: Wang MY, Liu TX, Li GD, Zhang TM. [Effects of bimolane and probimane on the incorporation of (3H)TdR, (3H)UR and (3H)Leu into Ehrlich ascites carcinoma cells iv vitro]. Zhongguo Yao Li Xue Bao. 1988 Jul;9(4):367-9. Chinese. PubMed PMID: 3195348. 13: Zhang YP, Chen YN, Fan GC, Xia SX. [Relationship between radiation sensitization and DNA damage by bimolane]. Zhongguo Yao Li Xue Bao. 1987 Mar;8(2):177-80. Chinese. PubMed PMID: 2959009. 14: Ren YF, Otter GM, Schmid FA. Further evaluation of bimolane and analogs as potential antitumor agents. Eur J Cancer Clin Oncol. 1985 Apr;21(4):493-7. PubMed PMID: 3859415. 15: Camerman N, Hempel A, Camerman A. Bimolane: structure determination indicates anticancer activity is attributable to ICRF-154. Science. 1984 Sep 14;225(4667):1165-6. PubMed PMID: 6474171. 16: Huang KW, Fu NW, Ren YF. [Effects of bimolane on size, metastases and cyclic AMP levels of Lewis lung carcinoma]. Zhongguo Yao Li Xue Bao. 1984 Mar;5(1):69-71. Chinese. PubMed PMID: 6326466. 17: Lin C, Zhang TM. [The cytokinetic effects of bimolane (AT-1727) on S180 cells]. Yao Xue Xue Bao. 1982 Sep;17(9):654-7. Chinese. PubMed PMID: 7158349. 18: Zhang TM, Chen ZY, Lin C. [Pharmacological studies on bimolane (AT-1727), a new antineoplastic agent (author's transl)]. Yao Xue Xue Bao. 1980 Oct;15(10):577-83. Chinese. PubMed PMID: 7257778.