CC-1065
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| Category | Antibiotics |
| Catalog number | BBF-02761 |
| CAS | 69866-21-3 |
| Molecular Weight | 703.70 |
| Molecular Formula | C37H33N7O8 |
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Description
CC-1065 is originally isolated from Streptomyces zelensis and its bioactivity was very strong. CC-1065 is against gram-positive bacteria with the MIC=1-10 ng/mL, against most gram-negative bacterial and fungi with the MIC of 1 μg/mL.
Specification
| Synonyms | Antibiotic CC 1065; NSC298223; CCRIS 2174 |
| IUPAC Name | 5-hydroxy-2-[5-hydroxy-4-methoxy-2-(3-methyl-7-oxo-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),3,8-triene-10-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-6-carbonyl]-4-methoxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-6-carboxamide |
| Canonical SMILES | CC1=CNC2=C1C34CC3CN(C4=CC2=O)C(=O)C5=CC6=C7CCN(C7=C(C(=C6N5)OC)O)C(=O)C8=CC9=C1CCN(C1=C(C(=C9N8)OC)O)C(=O)N |
| InChI | InChI=1S/C37H33N7O8/c1-14-12-39-27-22(45)10-23-37(24(14)27)11-15(37)13-44(23)35(49)21-9-18-16-4-6-42(28(16)30(46)32(51-2)25(18)41-21)34(48)20-8-19-17-5-7-43(36(38)50)29(17)31(47)33(52-3)26(19)40-20/h8-10,12,15,39-41,46-47H,4-7,11,13H2,1-3H3,(H2,38,50) |
| InChI Key | UOWVMDUEMSNCAV-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi |
| Boiling Point | 704.36°C at 760 mmHg |
| Density | 1.2929 g/cm3 |
Reference Reading
1. Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate
Taku Imaizumi, Yumi Yamashita, Yuki Nakazawa, Kentaro Okano, Juri Sakata, Hidetoshi Tokuyama Org Lett. 2019 Aug 16;21(16):6185-6189. doi: 10.1021/acs.orglett.9b01690. Epub 2019 Jun 12.
An indole synthesis via ring expansion of benzocyclobutenone oxime sulfonate was developed. Utility of the indole synthesis was demonstrated by the total synthesis of (+)-CC-1065. The middle and right segments were constructed by a sequential ring expansion of the symmetrical benzo-bis-cyclobutenone. The left segment was also constructed via ring expansion of the methyl-substituted benzocyclobutenone oxime sulfonates. After condensation of these three segments, the dienone cyclopropane structure was formed to complete the total synthesis.
2. Novel analogues of CC-1065 and the duocarmycins for the use in targeted tumour therapies
Lutz F Tietze, Birgit Krewer Anticancer Agents Med Chem. 2009 Mar;9(3):304-25. doi: 10.2174/1871520610909030304.
In recent years, a series of new and highly cytotoxic analogues of CC-1065 and the duocarmycins have been developed that can be transformed into much less toxic prodrugs for the use in antibody-directed enzyme prodrug therapy (ADEPT), gene-directed enzyme prodrug therapy (GDEPT) and prodrug monotherapy (PMT) of cancer. In all these approaches, a relatively non-toxic prodrug is applied and subsequently converted selectively in the tumour tissue into a highly cytotoxic drug, thus reducing undesired side effects accompanying conventional chemotherapy. Here, the design and biological evaluation of prodrugs based on analogues of CC-1065 and the duocarmycins for the use in tumour selective cancer therapies is reviewed. The advantage of this approach is the excellent therapeutic index of some of the new prodrugs of over 5000 and the high cytotoxicity of the corresponding drugs with IC(50) values of as low as 16 pM (IC(50): concentration required for 50 % growth inhibition of target cells). In addition, a novel method for the correlation of the alkylation efficiency and the cytotoxicity based on mass spectrometry is described.
3. Chemical and biological explorations of the family of CC-1065 and the duocarmycin natural products
Nandita Ghosh, Helen M Sheldrake, Mark Searcey, Klaus Pors Curr Top Med Chem. 2009;9(16):1494-524. doi: 10.2174/156802609789909812.
CC-1065, the duocarmycins and yatakemycin are members of a family of ultrapotent antitumour antibiotics that have been the subject of extensive investigations due to their mode of action and potential in the design of new anticancer therapeutics. The natural products and their analogues exert their effects through a sequence selective alkylation of duplex DNA in the minor groove at the N3 of adenine. An understanding of their structure and its effect on biological activity has been derived through chemical synthesis and has also generated new potential lead compounds. These studies form the first section of the review. The desire to progress these compounds to clinic has also led to studies of bioconjugation and prodrug formation and this is discussed in the second section of the review. The combination of synthesis with key biological experiments is a powerful tool to define the requirements for the development of natural products as potential therapeutic agents. The studies described herein form an excellent paradigm for the study and development of other natural products.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
