Carboquone
Carboquone is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.
1: DÃaz-Espinosa Y, Crespo-Hernández CE, AlegrÃa AE, GarcÃa C, Arce R. Quenching enhancement of the singlet excited state of pheophorbide-a by DNA in the presence of the quinone carboquone. Photochem Photobiol. 2011 Mar-Apr;87(2):275-83. doi: 10.1111/j.1751-1097.2010.00869.x. Epub 2011 Jan 4. PubMed PMID: 21138440; PubMed Central PMCID: PMC3070242.
2: Tabata M, Imagawa S, Tarumoto T, Ohmine K, Hatake K, Miura Y, Ozawa K. Essential thrombocythemia transformed to acute myelogenous leukemia with t(3;17)(p24; q12), del(5)(q13q34) after treatment with carboquone and hydroxyurea. Jpn J Clin Oncol. 2000 Jul;30(7):310-2. PubMed PMID: 11007164.
3: Takeuchi H, Baba H, Inutsuka S, Maehara Y, Sugimachi K. Potentiation of the cytotoxicity of carboquone by flavone acetic acid combined with hyperthermia. Anticancer Drugs. 1997 Sep;8(8):778-83. PubMed PMID: 9396622.
4: Ito H. [Experimental study and clinical application of a new combination chemotherapy with cis-platinum, adriamycin and carboquone in patients with advanced prostate cancer]. Nihon Ika Daigaku Zasshi. 1995 Oct;62(5):456-68. Japanese. PubMed PMID: 7499463.
5: Emi Y, Maehara Y, Kusumoto T, Baba H, Takahashi I, Yoshida M, Sugimachi K. Hydralazine combined with hyperthermia enhances the effects of carboquone. Oncology. 1994 Jul-Aug;51(4):339-43. PubMed PMID: 8208517.
6: Mäenpää JU, Heinonen E, Karnani P, Kauppila A, Kuoppala T, Salmi T, Sipilä P, Nieminen U. Carboquone combined with methotrexate and 5-fluorouracil for recurrent and advanced ovarian cancer. Eur J Cancer. 1993;29A(11):1633. PubMed PMID: 8217372.
7: Sampi K, Kuga T, Makishima M, Hattori M. [Intensive carboquone and cryopreserved autologous bone marrow transplantation for relapsed malignancies]. Gan To Kagaku Ryoho. 1992 Feb;19(2):257-9. Japanese. PubMed PMID: 1736840.
8: Sakaguchi Y, Kohnoe S, Emi Y, Maehara Y, Kusumoto T, Sugimachi K. Cytotoxicity of mitomycin C and carboquone combined with hyperthermia against hypoxic tumor cells in vitro. Oncology. 1992;49(3):227-32. PubMed PMID: 1495751.
9: Kusumoto T, Maehara Y, Sakaguchi Y, Kohnoe S, Emi Y, Sugimachi K. Sarcoma-180 cells and human colorectal tumor cells under in vitro hypoxic conditions are more sensitive to mitomycin C and carboquone. Eur J Surg Oncol. 1991 Aug;17(4):358-63. PubMed PMID: 1908390.
10: Kohnoe S, Emi Y, Takahashi I, Yoshida M, Maehara Y, Sugimachi K. Hypoxia and acidity increase the cytotoxicity of mitomycin C and carboquone to human tumor cells in vitro. Anticancer Res. 1991 Jul-Aug;11(4):1401-4. PubMed PMID: 1746896.
2: Tabata M, Imagawa S, Tarumoto T, Ohmine K, Hatake K, Miura Y, Ozawa K. Essential thrombocythemia transformed to acute myelogenous leukemia with t(3;17)(p24; q12), del(5)(q13q34) after treatment with carboquone and hydroxyurea. Jpn J Clin Oncol. 2000 Jul;30(7):310-2. PubMed PMID: 11007164.
3: Takeuchi H, Baba H, Inutsuka S, Maehara Y, Sugimachi K. Potentiation of the cytotoxicity of carboquone by flavone acetic acid combined with hyperthermia. Anticancer Drugs. 1997 Sep;8(8):778-83. PubMed PMID: 9396622.
4: Ito H. [Experimental study and clinical application of a new combination chemotherapy with cis-platinum, adriamycin and carboquone in patients with advanced prostate cancer]. Nihon Ika Daigaku Zasshi. 1995 Oct;62(5):456-68. Japanese. PubMed PMID: 7499463.
5: Emi Y, Maehara Y, Kusumoto T, Baba H, Takahashi I, Yoshida M, Sugimachi K. Hydralazine combined with hyperthermia enhances the effects of carboquone. Oncology. 1994 Jul-Aug;51(4):339-43. PubMed PMID: 8208517.
6: Mäenpää JU, Heinonen E, Karnani P, Kauppila A, Kuoppala T, Salmi T, Sipilä P, Nieminen U. Carboquone combined with methotrexate and 5-fluorouracil for recurrent and advanced ovarian cancer. Eur J Cancer. 1993;29A(11):1633. PubMed PMID: 8217372.
7: Sampi K, Kuga T, Makishima M, Hattori M. [Intensive carboquone and cryopreserved autologous bone marrow transplantation for relapsed malignancies]. Gan To Kagaku Ryoho. 1992 Feb;19(2):257-9. Japanese. PubMed PMID: 1736840.
8: Sakaguchi Y, Kohnoe S, Emi Y, Maehara Y, Kusumoto T, Sugimachi K. Cytotoxicity of mitomycin C and carboquone combined with hyperthermia against hypoxic tumor cells in vitro. Oncology. 1992;49(3):227-32. PubMed PMID: 1495751.
9: Kusumoto T, Maehara Y, Sakaguchi Y, Kohnoe S, Emi Y, Sugimachi K. Sarcoma-180 cells and human colorectal tumor cells under in vitro hypoxic conditions are more sensitive to mitomycin C and carboquone. Eur J Surg Oncol. 1991 Aug;17(4):358-63. PubMed PMID: 1908390.
10: Kohnoe S, Emi Y, Takahashi I, Yoshida M, Maehara Y, Sugimachi K. Hypoxia and acidity increase the cytotoxicity of mitomycin C and carboquone to human tumor cells in vitro. Anticancer Res. 1991 Jul-Aug;11(4):1401-4. PubMed PMID: 1746896.
| Chemical | |
|---|---|
| CAS Num | 24279-91-2 |
| Chemical Formula | C15H19N3O5 |
| Molecular Weight | 321.33 |
| IUPAC Chemical Name | 2-(2,5-di(aziridin-1-yl)-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-methoxyethyl carbamate |
| Exact Mass | 321.13247 |
| Elemental Analysis | C, 56.07; H, 5.96; N, 13.08; O, 24.90 |
| Synonym | carbazilquinone. 225bis(aziridin1yl)4methyl36dioxocyclohexa14dien1yl2methoxyethyl carbamate. |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | NC(OCC(C1=C(N2CC2)C(C(C)=C(N3CC3)C1=O)=O)OC)=O |
| Biological | |
| Targets and Effects | N/A |
| Pathways | alkylating agent |
| Physical | |
| 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). |
| Shelf Life | >2 years if stored properly |
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