Draft:Androprostamines A
| Submission declined on 9 June 2024 by Graeme Bartlett (talk). The smiles entry you provided is very weird, having oxygen with three bonds, and nitrogen with five. Where did you get this string from? see [1] for the plot. Anyway either fix the string to match the real substance or take it out.
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History[edit]
Androprostamine A (APA) is a natural product of Streptomyces sp MK932-CF8 strain. The APA-producing strain was isolated from a soil sample collected in Yokohama, Japan. Andropostamine A was isolated from the fermented broth with Adroprostamine B and Resormycin.[1] Andropostamine A was discovered as a novel inhibitor of Androgen Receptor (AR) functions through extensive screening of cultured broths from different microorganism. Androprostamine A showed potent inhibition against androgen-dependent proliferation of human prostate cancer LNCap and VCaP cells.[1] Androprostamines are known as peptide compounds that share similarities to resormycin but with three distinct non-proteinogenic amino acids. These non-proteinogenic amino acids are dehydroamino acid at the C- terminus,6-homolysine and hydroxyvaline.[2]
Preclinical Studies[edit]
Androprostamine A has been further studied in cancer since it was first isolated and has continued to be studied in prostate cancer. It has been tested on different cancer cell lines like breast, ovarian, etc., and even AR-negative prostate cancer. Still, it has demonstrated inhibition toward AR-positive prostate cancer, showing that it is highly selected for AR-positive prostate cancer.[3]
Mechanism of Action[edit]
Based on previous studies, APA is a potent inhibitor against androgen-dependent growth of LNCaP and VCaP cells, Its mechanism of inhibition is still unknown.[3]
Physicochemical properties[edit]
The chemical formula of Androprostamine A is C26H38ClN5O10. Its molecular weight is 615g/mol.[1]
Synthesis of Androprostamine A[edit]
The total synthesis was reported by Hikaru Abe and co-workers.[2]
| IUPAC NAME | N5-((S)-5-amino-7-(((S)-1-(((Z)-1-carboxy-2-(4-chloro-3,5-dihydroxyphenyl)vinyl)amino)-3-hydroxy-3-methyl-1-oxobutan-2-yl)amino)-7-oxoheptyl)glutamine |
| SMILE | C(C(N([C@H](C(N(C(=CC1=CC(=C(C(=C1)[O]([H])[H])Cl)[O]([H])[H])C(=O)[O]([H])[H])[H])=O)C(C([H])([H])[H])(C([H])([H])[H])[O]([H])[H])[H])=O)[C@H](CCCCN(C(CCC([N]([H])([H])([H])[H])C(=O)[O]([H])[H])=O)[H])[N]([H])([H])([H])[H] |
| InChI | 1S/C26H45ClN5O10.H2/c1-26(2,42)22(23(37)31-16(25(40)41)9-13-10-17(33)21(27)18(34)11-13)32-20(36)12-14(28)5-3-4-8-30-19(35)7-6-15(29)24(38)39;/h9-11,14-15,22H,3-8,12,33-34,42H2,1-2H3,28-29H4,(H,30,35)(H,31,37)(H,32,36)(H,38,39)(H,40,41);1H/b16-9-;/t14-,15?,22+;/m0./s1 |
| Chemical Formula | C26H38ClN5O10 |
| Molecular Weight | 615g/mol |
References[edit]
- ^ a b c Yamazaki, Yohko; Someno, Tetsuya; Igarashi, Masayuki; Kinoshita, Naoko; Hatano, Masaki; Kawada, Manabu; Momose, Isao; Nomoto, Akio (2015). "Androprostamines A and B, the new anti-prostate cancer agents produced by Streptomyces sp. MK932-CF8". The Journal of Antibiotics. 68 (4): 279–285. doi:10.1038/ja.2014.135. PMID 25269460.
- ^ a b Abe, Hikaru; Yamazaki, Yohko; Sakashita, Chiharu; Momose, Isao; Watanabe, Takumi; Shibasaki, Masakatsu (2016). "Synthesis of Androprostamine A and Resormycin". Chemical and Pharmaceutical Bulletin. 64 (7): 982–987. doi:10.1248/cpb.c16-00207. ISSN 1347-5223. PMID 27373659.
- ^ a b Yamazaki, Yohko; Abe, Hikaru; Sakashita, Chiharu; Ohba, Shun-Ichi; Watanabe, Takumi; Momose, Isao; Kawada, Manabu (2021). "Androprostamine A: a unique anti-prostate cancer agent". The Journal of Antibiotics. 74 (10): 717–725. doi:10.1038/s41429-021-00449-8. PMID 34321608.