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Declining submission: 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 [https://chemapps.stolaf.edu/jmol/jmol.... (AFCH)
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{{Draft topics|chemistry|medicine-and-health}}
{{Draft topics|chemistry|medicine-and-health}}
{{AfC topic|stem}}
{{AfC topic|stem}}
{{Chembox
<!-- Images -->
| ImageFile = Androprostamine A.svg
| ImageSize = 250px
| ImageFile1 = Androprostamine B.svg
| ImageSize1 = 250px
| ImageCaption1 = Chemical structures of androprostamine A (top) and androprostamine B
<!-- Names -->
| IUPACName =
| OtherNames =
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| index1_label = A
| index2_label = B
| CASNo1 = 1570045-05-4
| CASNo2 = 1570045-06-5
| PubChem =
| SMILES1 = C(=C(\NC([C@@H](NC(C[C@H](CCCCNC(CC[C@@H](C(O)=O)N)=O)N)=O)[C@@](C)(C)O)=O)/C(O)=O)\C1=CC(O)=C(Cl)C(O)=C1
| SMILES2 = C(=C(NC(C(NC(CC(CCCCNC(CCC(NC(=O)C1CCCN1)C(O)=O)=O)N)=O)C(C)(C)O)=O)C(O)=O)C2=CC(O)=C(Cl)C(O)=C2
⚫
| InChI1 = 1S/C26H38ClN5O10/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/h9-11,14-15,22,33-34,42H,3-8,12,28-29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,38,39)(H,40,41)/b16-9-/t14-,15-,22+/m0/s1
| InChI2 = 1S/C31H45ClN6O11/c1-31(2,49)26(28(44)37-20(30(47)48)12-16-13-21(39)25(32)22(40)14-16)38-24(42)15-17(33)6-3-4-10-35-23(41)9-8-19(29(45)46)36-27(43)18-7-5-11-34-18/h12-14,17-19,26,34,39-40,49H,3-11,15,33H2,1-2H3,(H,35,41)(H,36,43)(H,37,44)(H,38,42)(H,45,46)(H,47,48)
| InChIKey1 = UEIVDLBQUOWRJU-PCCGUAOVSA-N
| InChIKey2 = BYUWOLFRQQSZLA-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
⚫
| Formula = A: C<sub>26</sub>H<sub>38</sub>ClN<sub>5</sub>O<sub>10</sub> <br> B: C<sub>31</sub>H<sub>45</sub>ClN<sub>6</sub>O<sub>11</sub>
| MolarMass = A: 616.06 g/mol <br> B: 713.18 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
⚫
}}

'''Androprostamines''' are a pair of chemical compounds isolated from ''[[Streptomyces]]''. They are designated androprostamine A and androprostamine B.


== History ==
== History ==
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.<ref name="Yamazaki">{{cite journal |last1=Yamazaki |first1=Yohko |last2=Someno |first2=Tetsuya |last3=Igarashi |first3=Masayuki |last4=Kinoshita |first4=Naoko |last5=Hatano |first5=Masaki |last6=Kawada |first6=Manabu |last7=Momose |first7=Isao |last8=Nomoto |first8=Akio |title=Androprostamines A and B, the new anti-prostate cancer agents produced by Streptomyces sp. MK932-CF8 |journal=The Journal of Antibiotics |date=2015 |volume=68 |issue=4 |pages=279–285 |doi=10.1038/ja.2014.135 |pmid=25269460 }}</ref>
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 along with androprostamine B and the related chemical compound [[resormycin]].<ref name="Yamazaki">{{cite journal |last1=Yamazaki |first1=Yohko |last2=Someno |first2=Tetsuya |last3=Igarashi |first3=Masayuki |last4=Kinoshita |first4=Naoko |last5=Hatano |first5=Masaki |last6=Kawada |first6=Manabu |last7=Momose |first7=Isao |last8=Nomoto |first8=Akio |title=Androprostamines A and B, the new anti-prostate cancer agents produced by Streptomyces sp. MK932-CF8 |journal=The Journal of Antibiotics |date=2015 |volume=68 |issue=4 |pages=279–285 |doi=10.1038/ja.2014.135 |pmid=25269460 }}</ref> 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.<ref name="Abe">{{cite journal |last1=Abe |first1=Hikaru |last2=Yamazaki |first2=Yohko |last3=Sakashita |first3=Chiharu |last4=Momose |first4=Isao |last5=Watanabe |first5=Takumi |last6=Shibasaki |first6=Masakatsu |title=Synthesis of Androprostamine A and Resormycin |journal=Chemical and Pharmaceutical Bulletin |date=2016 |volume=64 |issue=7 |pages=982–987 |doi=10.1248/cpb.c16-00207 |pmid=27373659 |issn=1347-5223}}</ref>
⚫
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.<ref name="Yamazaki"/>
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.<ref name="Abe">{{cite journal |last1=Abe |first1=Hikaru |last2=Yamazaki |first2=Yohko |last3=Sakashita |first3=Chiharu |last4=Momose |first4=Isao |last5=Watanabe |first5=Takumi |last6=Shibasaki |first6=Masakatsu |title=Synthesis of Androprostamine A and Resormycin |journal=Chemical and Pharmaceutical Bulletin |date=2016 |volume=64 |issue=7 |pages=982–987 |doi=10.1248/cpb.c16-00207 |pmid=27373659 |issn=1347-5223}}</ref>


== Preclinical Studies ==
== Preclinical study ==

⚫
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.<ref name="YamazakiA"/>
⚫
Andropostamine A is a an inhibitor of the [[androgen receptor]] (AR) and was discovered through extensive screening of cultured broths from different microorganisms. Androprostamine A showed potent inhibition against androgen-dependent proliferation of human prostate cancer LNCap and VCaP cells.<ref name="Yamazaki"/>
⚫
== Mechanism of Action ==

⚫
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 such as [[breast cancer|breast]], [[ovarian cancer|ovarian]], and even AR-negative prostate cancers. Still, it has demonstrated inhibition toward AR-positive prostate cancer, showing that it is highly selective for AR-positive prostate cancer.<ref name="YamazakiA"/>

⚫
== Mechanism of action ==


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.<ref name="YamazakiA">{{cite journal |last1=Yamazaki |first1=Yohko |last2=Abe |first2=Hikaru |last3=Sakashita |first3=Chiharu |last4=Ohba |first4=Shun-Ichi |last5=Watanabe |first5=Takumi |last6=Momose |first6=Isao |last7=Kawada |first7=Manabu |title=Androprostamine A: a unique anti-prostate cancer agent |journal=The Journal of Antibiotics |date=2021 |volume=74 |issue=10 |pages=717–725 |doi=10.1038/s41429-021-00449-8 |pmid=34321608 }}</ref>
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.<ref name="YamazakiA">{{cite journal |last1=Yamazaki |first1=Yohko |last2=Abe |first2=Hikaru |last3=Sakashita |first3=Chiharu |last4=Ohba |first4=Shun-Ichi |last5=Watanabe |first5=Takumi |last6=Momose |first6=Isao |last7=Kawada |first7=Manabu |title=Androprostamine A: a unique anti-prostate cancer agent |journal=The Journal of Antibiotics |date=2021 |volume=74 |issue=10 |pages=717–725 |doi=10.1038/s41429-021-00449-8 |pmid=34321608 }}</ref>


== Physicochemical properties ==
== Physicochemical properties ==
The chemical formula of Androprostamine A is C26H38ClN5O10. Its molecular weight is 615g/mol.<ref name="Yamazaki"/>
The chemical formulas of androprostamines A and B are C<sub>26</sub>H<sub>38</sub>ClN<sub>5</sub>O<sub>10</sub> and C<sub>31</sub>H<sub>45</sub>ClN<sub>6</sub>O<sub>11</sub>, respectively. Their molecular weights are 616.06 g/mol and 713.18 g/mol.<ref name="Yamazaki"/>


== Synthesis of Androprostamine A==
== Synthesis ==
The total synthesis was reported by Hikaru Abe and co-workers.<ref name="Abe"/>
A [[total synthesis]] of androprostamine A was reported by Hikaru Abe and co-workers.<ref name="Abe"/>


{| class="wikitable"
|+ Identifiers
|-
| 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
⚫
|}

{| class="wikitable"
|+ Properties
|-
⚫
| Chemical Formula || C<sub>26</sub>H<sub>38</sub>ClN<sub>5</sub>O<sub>10</sub>
|-
| Molecular Weight || 615g/mol
|}
== References ==
== References ==
<!-- Inline citations added to your article will automatically display here. See en.wikipedia.org/wiki/WP:REFB for instructions on how to add citations. -->
{{reflist}}
{{reflist}}

[[Category:Chloroarenes]]
[[Category:Phenols]]
[[Category:Carboxylic acids]]
[[Category:Amino acid derivatives]]

Revision as of 00:51, 4 September 2024

Androprostamine

Chemical structures of androprostamine A (top) and androprostamine B
Identifiers
3D model (JSmol)
  • A: InChI=1S/C26H38ClN5O10/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/h9-11,14-15,22,33-34,42H,3-8,12,28-29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,38,39)(H,40,41)/b16-9-/t14-,15-,22+/m0/s1
    Key: UEIVDLBQUOWRJU-PCCGUAOVSA-N
  • B: InChI=1S/C31H45ClN6O11/c1-31(2,49)26(28(44)37-20(30(47)48)12-16-13-21(39)25(32)22(40)14-16)38-24(42)15-17(33)6-3-4-10-35-23(41)9-8-19(29(45)46)36-27(43)18-7-5-11-34-18/h12-14,17-19,26,34,39-40,49H,3-11,15,33H2,1-2H3,(H,35,41)(H,36,43)(H,37,44)(H,38,42)(H,45,46)(H,47,48)
    Key: BYUWOLFRQQSZLA-UHFFFAOYSA-N
  • A: C(=C(\NC([C@@H](NC(C[C@H](CCCCNC(CC[C@@H](C(O)=O)N)=O)N)=O)[C@@](C)(C)O)=O)/C(O)=O)\C1=CC(O)=C(Cl)C(O)=C1
  • B: C(=C(NC(C(NC(CC(CCCCNC(CCC(NC(=O)C1CCCN1)C(O)=O)=O)N)=O)C(C)(C)O)=O)C(O)=O)C2=CC(O)=C(Cl)C(O)=C2
Properties
A: C26H38ClN5O10
B: C31H45ClN6O11
Molar mass A: 616.06 g/mol
B: 713.18 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Androprostamines are a pair of chemical compounds isolated from Streptomyces. They are designated androprostamine A and androprostamine B.

History

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 along with androprostamine B and the related chemical compound resormycin.[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 study

Andropostamine A is a an inhibitor of the androgen receptor (AR) and was discovered through extensive screening of cultured broths from different microorganisms. Androprostamine A showed potent inhibition against androgen-dependent proliferation of human prostate cancer LNCap and VCaP cells.[1]

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 such as breast, ovarian, and even AR-negative prostate cancers. Still, it has demonstrated inhibition toward AR-positive prostate cancer, showing that it is highly selective for AR-positive prostate cancer.[3]

Mechanism of action

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

The chemical formulas of androprostamines A and B are C26H38ClN5O10 and C31H45ClN6O11, respectively. Their molecular weights are 616.06 g/mol and 713.18 g/mol.[1]

Synthesis

A total synthesis of androprostamine A was reported by Hikaru Abe and co-workers.[2]

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
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