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{{Short description|Group of antibiotics}}
{{About|mitomycins as a family of natural products|its use as a medication|Mitomycin C}}
[[File:Mitomycin.svg|thumb|right|Chemical structure of [[mitomycin C]]]]
[[File:Mitomycin.svg|thumb|right|Chemical structure of [[mitomycin C]]]]
The '''mitomycins''' are a family of [[aziridine]]-containing [[Secondary metabolite|natural products]] isolated from ''[[Streptomyces caespitosus]]'' or ''[[Streptomyces lavendulae]].''<ref>{{Cite book|title=Bacteriophages : methods and protocols|last=Clokie|first=Martha R. J. |authorlink1=Martha Clokie |last2=Kropinski|first2=Andrew M. (Andrew Maitland Boleslaw)|date=2009|publisher=Humana Press|isbn=9781603271646|oclc=297169927}}</ref><ref>{{cite journal|vauthors=Danshiitsoodol N, de Pinho CA, Matoba Y, Kumagai T, Sugiyama M |title=The mitomycin C (MMC)-binding protein from MMC-producing microorganisms protects from the lethal effect of bleomycin: crystallographic analysis to elucidate the binding mode of the antibiotic to the protein|journal=J Mol Biol|volume=360|issue=2|year=2006|pages=398–408|doi=10.1016/j.jmb.2006.05.017|pmid=16756991}}</ref> They include '''mitomycin A''', '''mitomycin B''', and '''mitomycin C'''. When the name mitomycin occurs alone, it usually refers to mitomycin C, its [[international nonproprietary name]]. Mitomycin C is used as a medicine for treating various disorders associated with the growth and spread of cells.
The '''mitomycins''' are a family of [[aziridine]]-containing [[Secondary metabolite|natural products]] isolated from ''[[Streptomyces caespitosus]]'' or ''[[Streptomyces lavendulae]].''<ref>{{Cite book|title=Bacteriophages : methods and protocols| vauthors = Clokie MR, Kropinski AM |author-link1=Martha Clokie |date=2009|publisher=Humana Press|isbn=9781603271646|oclc=297169927}}</ref><ref>{{cite journal | vauthors = Danshiitsoodol N, de Pinho CA, Matoba Y, Kumagai T, Sugiyama M | title = The mitomycin C (MMC)-binding protein from MMC-producing microorganisms protects from the lethal effect of bleomycin: crystallographic analysis to elucidate the binding mode of the antibiotic to the protein | journal = Journal of Molecular Biology | volume = 360 | issue = 2 | pages = 398–408 | date = July 2006 | pmid = 16756991 | doi = 10.1016/j.jmb.2006.05.017 }}</ref> They include mitomycin A, mitomycin B, and [[mitomycin C]]. When the name mitomycin occurs alone, it usually refers to mitomycin C, its [[international nonproprietary name]]. Mitomycin C is used as a medicine for treating various disorders associated with the growth and spread of cells.


== Biosynthesis ==
== Biosynthesis ==
In general, the biosynthesis of all mitomycins proceeds via combination of 3-amino-5-hydroxybenzoic acid (AHBA), D-glucosamine, and carbamoyl phosphate, to form the mitosane core, followed by specific tailoring steps.<ref name=Sherman>{{cite journal |author1=Mao Y. |author2=Varoglu M. |author3=Sherman D.H. | title = Molecular characterization and analysis of the biosynthetic gene cluster for the antitumor antibiotic mitomycin C from Streptomyces Iavendulae NRRL 2564. | journal = Chemistry and Biology | volume = 6 | issue = 4 | pages = 251–263 |date=April 1999 | doi=10.1016/S1074-5521(99)80040-4 | pmid = 10099135| doi-access = free }}</ref> The key intermediate, AHBA, is a common precursor to other anticancer drugs, such as [[rifamycin]] and ansamycin.
In general, the biosynthesis of all mitomycins proceeds via combination of 3-amino-5-hydroxybenzoic acid (AHBA), [[D-glucosamine|<small>D</small>-glucosamine]], and [[carbamoyl phosphate]], to form the mitosane core, followed by specific tailoring steps.<ref name=Sherman>{{cite journal | vauthors = Mao Y, Varoglu M, Sherman DH | title = Molecular characterization and analysis of the biosynthetic gene cluster for the antitumor antibiotic mitomycin C from Streptomyces lavendulae NRRL 2564 | journal = Chemistry & Biology | volume = 6 | issue = 4 | pages = 251–263 | date = April 1999 | pmid = 10099135 | doi = 10.1016/S1074-5521(99)80040-4 | doi-access = free }}</ref> The key intermediate, AHBA, is a common precursor to other anticancer drugs, such as [[rifamycin]] and ansamycin.


Specifically, the biosynthesis begins with the addition of [[phosphoenolpyruvate]] (PEP) to [[erythrose-4-phosphate]] (E4P) with a yet undiscovered enzyme, which is then ammoniated to give 4-amino-3-deoxy-<small>D</small>-arabino heptulosonic acid-7-phosphate (aminoDHAP). Next, [[DHQ synthase]] catalyzes a ring closure to give 4-amino3-dehydroquinate (aminoDHQ), which then undergoes a double oxidation via aminoDHQ dehydratase to give 4-amino-dehydroshikimate (aminoDHS). The key intermediate, 3-amino-5-hydroxybenzoic acid (AHBA), is made via aromatization by AHBA synthase.
Specifically, the biosynthesis begins with the addition of [[phosphoenolpyruvate]] (PEP) to [[erythrose-4-phosphate]] (E4P) with a yet undiscovered enzyme, which is then ammoniated to give 4-amino-3-deoxy-<small>D</small>-arabino heptulosonic acid-7-phosphate (aminoDHAP). Next, [[DHQ synthase]] catalyzes a ring closure to give 4-amino3-dehydroquinate (aminoDHQ), which then undergoes a double oxidation via aminoDHQ dehydratase to give 4-amino-dehydroshikimate (aminoDHS). The key intermediate, 3-amino-5-hydroxybenzoic acid (AHBA), is made via aromatization by AHBA synthase.
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==Biological effects==
==Biological effects==
In the bacterium ''[[Legionella pneumophila]]'', [[mitomycin C]] induces [[Natural competence|competence]] for [[Transformation (genetics)|transformation]].<ref>{{cite journal |vauthors=Charpentier X, Kay E, Schneider D, Shuman HA |title=Antibiotics and UV radiation induce competence for natural transformation in Legionella pneumophila |journal=J. Bacteriol. |volume=193 |issue=5 |pages=1114–21 |date=March 2011 |pmid=21169481 |pmc=3067580 |doi=10.1128/JB.01146-10 |url=}}</ref> [[Transformation (genetics)#Natural transformation|Natural transformation]] is a process of DNA transfer between cells, and is regarded as a form of bacterial sexual interaction. In the fruit fly ''[[Drosophila melanogaster]]'', exposure to mitomycin C increases recombination during meiosis, a key stage of the sexual cycle.<ref>{{cite journal |vauthors=Schewe MJ, Suzuki DT, Erasmus U |title=The genetic effects of mitomycin C in Drosophila melanogaster. II. Induced meiotic recombination |journal=Mutat. Res. |volume=12 |issue=3 |pages=269–79 |date=July 1971 |pmid=5563942 |doi= 10.1016/0027-5107(71)90015-7 }}</ref> In the plant ''[[Arabidopsis thaliana]]'', mutant strains defective in genes necessary for recombination during meiosis and mitosis are hypersensitive to killing by mitomycin C.<ref>{{cite journal |vauthors=Bleuyard JY, Gallego ME, Savigny F, White CI |title=Differing requirements for the Arabidopsis Rad51 paralogs in meiosis and DNA repair |journal=Plant J. |volume=41 |issue=4 |pages=533–45 |date=February 2005 |pmid=15686518 |doi=10.1111/j.1365-313X.2004.02318.x |url=}}</ref>
In the bacterium ''[[Legionella pneumophila]]'', [[mitomycin C]] induces [[Natural competence|competence]] for [[Transformation (genetics)|transformation]].<ref>{{cite journal | vauthors = Charpentier X, Kay E, Schneider D, Shuman HA | title = Antibiotics and UV radiation induce competence for natural transformation in Legionella pneumophila | journal = Journal of Bacteriology | volume = 193 | issue = 5 | pages = 1114–1121 | date = March 2011 | pmid = 21169481 | pmc = 3067580 | doi = 10.1128/JB.01146-10 }}</ref> [[Transformation (genetics)#Natural transformation|Natural transformation]] is a process of DNA transfer between cells, and is regarded as a form of bacterial sexual interaction. In the fruit fly ''[[Drosophila melanogaster]]'', exposure to mitomycin C increases recombination during meiosis, a key stage of the sexual cycle.<ref>{{cite journal | vauthors = Schewe MJ, Suzuki DT, Erasmus U | title = The genetic effects of mitomycin C in Drosophila melanogaster. II. Induced meiotic recombination | journal = Mutation Research | volume = 12 | issue = 3 | pages = 269–279 | date = July 1971 | pmid = 5563942 | doi = 10.1016/0027-5107(71)90015-7 }}</ref> In the plant ''[[Arabidopsis thaliana]]'', mutant strains defective in genes necessary for recombination during meiosis and mitosis are hypersensitive to killing by mitomycin C.<ref>{{cite journal | vauthors = Bleuyard JY, Gallego ME, Savigny F, White CI | title = Differing requirements for the Arabidopsis Rad51 paralogs in meiosis and DNA repair | journal = The Plant Journal | volume = 41 | issue = 4 | pages = 533–545 | date = February 2005 | pmid = 15686518 | doi = 10.1111/j.1365-313X.2004.02318.x | doi-access = }}</ref>


==Medicinal uses and research==
==Medicinal uses and research==
Mitomycin C has been shown to have activity against [[Stationary phase (biology)|stationary phase]] [[Multidrug tolerance|persisters]] caused by ''[[Borrelia burgdorferi]]'', a factor in [[lyme disease]].<ref>{{cite journal|last1=Feng|first1=Jie|last2=Shi|first2=Wanliang|last3=Zhang|first3=Shuo|last4=Zhang|first4=Ying|title=Identification of new compounds with high activity against stationary phase Borrelia burgdorferi from the NCI compound collection|journal=Emerging Microbes & Infections|date=3 June 2015|volume=4|issue=5|pages=e31|doi=10.1038/emi.2015.31|pmid=26954881|pmc=5176177}}</ref><ref>{{cite journal|last1=Sharma|first1=Bijaya|last2=Brown|first2=Autumn V.|last3=Matluck|first3=Nicole E.|last4=Hu|first4=Linden T.|last5=Lewis|first5=Kim|title=Borrelia burgdorferi, the Causative Agent of Lyme Disease, Forms Drug-Tolerant Persister Cells|journal=Antimicrobial Agents and Chemotherapy|date=26 May 2015|pages=AAC.00864–15|doi=10.1128/AAC.00864-15|volume=59|issue=8|pmid=26014929|pmc=4505243}}</ref> Mitomycin C is used to treat symptoms of [[pancreatic cancer|pancreatic]] and [[stomach cancer]],<ref>{{cite web|url=https://www.drugs.com/mtm/mitomycin.html|title=Mitomycin|publisher=Drugs.com|date=2017|accessdate=11 November 2017}}</ref> and is under [[clinical research]] for its potential to treat [[gastrointestinal]] [[stricture (medicine)|strictures]],<ref>{{cite journal|pmid=25626632|year=2015|last1=Rustagi|first1=T|title=Treatment of Refractory Gastrointestinal Strictures with Mitomycin C: A Systematic Review|journal=Journal of Clinical Gastroenterology|volume=49|issue=10|pages=837–47|last2=Aslanian|first2=H. R|last3=Laine|first3=L|doi=10.1097/MCG.0000000000000295}}</ref> wound healing from [[glaucoma]] surgery,<ref>{{cite journal|pmid=26545176|year=2015|last1=Cabourne|first1=E|title=Mitomycin C versus 5-fluorouracil for wound healing in glaucoma surgery|journal=The Cochrane Database of Systematic Reviews|issue=11|pages=CD006259|last2=Clarke|first2=J. C|last3=Schlottmann|first3=P. G|last4=Evans|first4=J. R|doi=10.1002/14651858.CD006259.pub2|url=https://researchonline.lshtm.ac.uk/4086913/1/Mitomycin%20C%20versus%205-Fluorouracil_COCHREV.pdf}}</ref> corneal excimer laser surgery<ref>{{Cite journal|last=Majmudar|first=Parag A|last2=Forstot|first2=S.Lance|last3=Dennis|first3=Richard F|last4=Nirankari|first4=Verinder S|last5=Damiano|first5=Richard E|last6=Brenart|first6=Robert|last7=Epstein|first7=Randy J|date=January 2000|title=Topical Mitomycin-C for subepithelial fibrosis after refractive corneal surgery|journal=Ophthalmology|volume=107|issue=1|pages=89–94|doi=10.1016/s0161-6420(99)00019-6|pmid=10647725|issn=0161-6420}}</ref> and [[endoscope|endoscopic]] [[dacryocystorhinostomy]].<ref>{{cite journal|pmc=3652813|year=2013|last1=Cheng|first1=S. M|title=Efficacy of Mitomycin C in Endoscopic Dacryocystorhinostomy: A Systematic Review and Meta-Analysis|journal=PLoS ONE|volume=8|issue=5|pages=e62737|last2=Feng|first2=Y. F|last3=Xu|first3=L|last4=Li|first4=Y|last5=Huang|first5=J. H|doi=10.1371/journal.pone.0062737|pmid=23675423|bibcode=2013PLoSO...862737C}}</ref>
Mitomycin C has been shown to have activity against [[Stationary phase (biology)|stationary phase]] [[Multidrug tolerance|persisters]] caused by ''[[Borrelia burgdorferi]]'', a factor in [[lyme disease]].<ref>{{cite journal | vauthors = Feng J, Shi W, Zhang S, Zhang Y | title = Identification of new compounds with high activity against stationary phase Borrelia burgdorferi from the NCI compound collection | journal = Emerging Microbes & Infections | volume = 4 | issue = 6 | pages = e31 | date = June 2015 | pmid = 26954881 | pmc = 5176177 | doi = 10.1038/emi.2015.31 }}</ref><ref>{{cite journal | vauthors = Sharma B, Brown AV, Matluck NE, Hu LT, Lewis K | title = Borrelia burgdorferi, the Causative Agent of Lyme Disease, Forms Drug-Tolerant Persister Cells | journal = Antimicrobial Agents and Chemotherapy | volume = 59 | issue = 8 | pages = 4616–4624 | date = August 2015 | pmid = 26014929 | pmc = 4505243 | doi = 10.1128/AAC.00864-15 }}</ref> Mitomycin C is used to treat [[pancreatic cancer|pancreatic]] and [[stomach cancer]],<ref>{{cite web|url=https://www.drugs.com/mtm/mitomycin.html|title=Mitomycin|publisher=Drugs.com|date=2017|access-date=11 November 2017}}</ref> and is under [[clinical research]] for its potential to treat [[gastrointestinal]] [[stricture (medicine)|strictures]],<ref>{{cite journal | vauthors = Rustagi T, Aslanian HR, Laine L | title = Treatment of Refractory Gastrointestinal Strictures With Mitomycin C: A Systematic Review | journal = Journal of Clinical Gastroenterology | volume = 49 | issue = 10 | pages = 837–847 | year = 2015 | pmid = 25626632 | doi = 10.1097/MCG.0000000000000295 | s2cid = 5867992 }}</ref> wound healing from [[glaucoma]] surgery,<ref>{{cite journal | vauthors = Cabourne E, Clarke JC, Schlottmann PG, Evans JR | title = Mitomycin C versus 5-Fluorouracil for wound healing in glaucoma surgery | journal = The Cochrane Database of Systematic Reviews | volume = 2015 | issue = 11 | pages = CD006259 | date = November 2015 | pmid = 26545176 | pmc = 8763343 | doi = 10.1002/14651858.CD006259.pub2 }}</ref> corneal excimer laser surgery<ref>{{cite journal | vauthors = Majmudar PA, Forstot SL, Dennis RF, Nirankari VS, Damiano RE, Brenart R, Epstein RJ | title = Topical mitomycin-C for subepithelial fibrosis after refractive corneal surgery | journal = Ophthalmology | volume = 107 | issue = 1 | pages = 89–94 | date = January 2000 | pmid = 10647725 | doi = 10.1016/s0161-6420(99)00019-6 }}</ref> and [[endoscope|endoscopic]] [[dacryocystorhinostomy]].<ref>{{cite journal | vauthors = Cheng SM, Feng YF, Xu L, Li Y, Huang JH | title = Efficacy of mitomycin C in endoscopic dacryocystorhinostomy: a systematic review and meta-analysis | journal = PLOS ONE | volume = 8 | issue = 5 | pages = e62737 | year = 2013 | pmid = 23675423 | pmc = 3652813 | doi = 10.1371/journal.pone.0062737 | doi-access = free | bibcode = 2013PLoSO...862737C }}</ref>


== References ==
== References ==
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[[Category:Aziridines]]
[[Category:Aziridines]]
[[Category:Nitrogen heterocycles]]
[[Category:Nitrogen heterocycles]]
[[Category:Heterocyclic compounds (4 or more rings)]]
[[Category:Heterocyclic compounds with 4 rings]]
[[Category:Enones]]
[[Category:Enones]]
[[Category:Methoxy compounds]]

Latest revision as of 14:07, 17 January 2024

This article is about mitomycins as a family of natural products. For its use as a medication, see Mitomycin C.
Chemical structure of mitomycin C

The mitomycins are a family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.[1][2] They include mitomycin A, mitomycin B, and mitomycin C. When the name mitomycin occurs alone, it usually refers to mitomycin C, its international nonproprietary name. Mitomycin C is used as a medicine for treating various disorders associated with the growth and spread of cells.

Biosynthesis

[edit]

In general, the biosynthesis of all mitomycins proceeds via combination of 3-amino-5-hydroxybenzoic acid (AHBA), D-glucosamine, and carbamoyl phosphate, to form the mitosane core, followed by specific tailoring steps.[3] The key intermediate, AHBA, is a common precursor to other anticancer drugs, such as rifamycin and ansamycin.

Specifically, the biosynthesis begins with the addition of phosphoenolpyruvate (PEP) to erythrose-4-phosphate (E4P) with a yet undiscovered enzyme, which is then ammoniated to give 4-amino-3-deoxy-D-arabino heptulosonic acid-7-phosphate (aminoDHAP). Next, DHQ synthase catalyzes a ring closure to give 4-amino3-dehydroquinate (aminoDHQ), which then undergoes a double oxidation via aminoDHQ dehydratase to give 4-amino-dehydroshikimate (aminoDHS). The key intermediate, 3-amino-5-hydroxybenzoic acid (AHBA), is made via aromatization by AHBA synthase.

Synthesis of the key intermediate, 3-amino-5-hydroxy-benzoic acid.

The mitosane core is synthesized as shown below via condensation of AHBA and D-glucosamine, although no specific enzyme has been characterized that mediates this transformation. Once this condensation has occurred, the mitosane core is tailored by a variety of enzymes. Both the sequence and the identity of these steps are yet to be determined.

  • Complete reduction of C-6 – Likely via F420-dependent tetrahydromethanopterin (H4MPT) reductase and H4MPT:CoM methyltransferase
  • Hydroxylation of C-5, C-7 (followed by transamination), and C-9a. – Likely via cytochrome P450 monooxygenase or benzoate hydroxylase
  • O-Methylation at C-9a – Likely via SAM dependent methyltransferase
  • Oxidation at C-5 and C8 – Unknown
  • Intramolecular amination to form aziridine – Unknown
  • Carbamoylation at C-10 – Carbamoyl transferase, with carbamoyl phosphate (C4P) being derived from L-citrulline or L-arginine

Biological effects

[edit]

In the bacterium Legionella pneumophila, mitomycin C induces competence for transformation.[4] Natural transformation is a process of DNA transfer between cells, and is regarded as a form of bacterial sexual interaction. In the fruit fly Drosophila melanogaster, exposure to mitomycin C increases recombination during meiosis, a key stage of the sexual cycle.[5] In the plant Arabidopsis thaliana, mutant strains defective in genes necessary for recombination during meiosis and mitosis are hypersensitive to killing by mitomycin C.[6]

Medicinal uses and research

[edit]

Mitomycin C has been shown to have activity against stationary phase persisters caused by Borrelia burgdorferi, a factor in lyme disease.[7][8] Mitomycin C is used to treat pancreatic and stomach cancer,[9] and is under clinical research for its potential to treat gastrointestinal strictures,[10] wound healing from glaucoma surgery,[11] corneal excimer laser surgery[12] and endoscopic dacryocystorhinostomy.[13]

References

[edit]
  1. ^ Clokie MR, Kropinski AM (2009). Bacteriophages : methods and protocols. Humana Press. ISBN 9781603271646. OCLC 297169927.
  2. ^ Danshiitsoodol N, de Pinho CA, Matoba Y, Kumagai T, Sugiyama M (July 2006). "The mitomycin C (MMC)-binding protein from MMC-producing microorganisms protects from the lethal effect of bleomycin: crystallographic analysis to elucidate the binding mode of the antibiotic to the protein". Journal of Molecular Biology. 360 (2): 398–408. doi:10.1016/j.jmb.2006.05.017. PMID 16756991.
  3. ^ Mao Y, Varoglu M, Sherman DH (April 1999). "Molecular characterization and analysis of the biosynthetic gene cluster for the antitumor antibiotic mitomycin C from Streptomyces lavendulae NRRL 2564". Chemistry & Biology. 6 (4): 251–263. doi:10.1016/S1074-5521(99)80040-4. PMID 10099135.
  4. ^ Charpentier X, Kay E, Schneider D, Shuman HA (March 2011). "Antibiotics and UV radiation induce competence for natural transformation in Legionella pneumophila". Journal of Bacteriology. 193 (5): 1114–1121. doi:10.1128/JB.01146-10. PMC 3067580. PMID 21169481.
  5. ^ Schewe MJ, Suzuki DT, Erasmus U (July 1971). "The genetic effects of mitomycin C in Drosophila melanogaster. II. Induced meiotic recombination". Mutation Research. 12 (3): 269–279. doi:10.1016/0027-5107(71)90015-7. PMID 5563942.
  6. ^ Bleuyard JY, Gallego ME, Savigny F, White CI (February 2005). "Differing requirements for the Arabidopsis Rad51 paralogs in meiosis and DNA repair". The Plant Journal. 41 (4): 533–545. doi:10.1111/j.1365-313X.2004.02318.x. PMID 15686518.
  7. ^ Feng J, Shi W, Zhang S, Zhang Y (June 2015). "Identification of new compounds with high activity against stationary phase Borrelia burgdorferi from the NCI compound collection". Emerging Microbes & Infections. 4 (6): e31. doi:10.1038/emi.2015.31. PMC 5176177. PMID 26954881.
  8. ^ Sharma B, Brown AV, Matluck NE, Hu LT, Lewis K (August 2015). "Borrelia burgdorferi, the Causative Agent of Lyme Disease, Forms Drug-Tolerant Persister Cells". Antimicrobial Agents and Chemotherapy. 59 (8): 4616–4624. doi:10.1128/AAC.00864-15. PMC 4505243. PMID 26014929.
  9. ^ "Mitomycin". Drugs.com. 2017. Retrieved 11 November 2017.
  10. ^ Rustagi T, Aslanian HR, Laine L (2015). "Treatment of Refractory Gastrointestinal Strictures With Mitomycin C: A Systematic Review". Journal of Clinical Gastroenterology. 49 (10): 837–847. doi:10.1097/MCG.0000000000000295. PMID 25626632. S2CID 5867992.
  11. ^ Cabourne E, Clarke JC, Schlottmann PG, Evans JR (November 2015). "Mitomycin C versus 5-Fluorouracil for wound healing in glaucoma surgery". The Cochrane Database of Systematic Reviews. 2015 (11): CD006259. doi:10.1002/14651858.CD006259.pub2. PMC 8763343. PMID 26545176.
  12. ^ Majmudar PA, Forstot SL, Dennis RF, Nirankari VS, Damiano RE, Brenart R, Epstein RJ (January 2000). "Topical mitomycin-C for subepithelial fibrosis after refractive corneal surgery". Ophthalmology. 107 (1): 89–94. doi:10.1016/s0161-6420(99)00019-6. PMID 10647725.
  13. ^ Cheng SM, Feng YF, Xu L, Li Y, Huang JH (2013). "Efficacy of mitomycin C in endoscopic dacryocystorhinostomy: a systematic review and meta-analysis". PLOS ONE. 8 (5): e62737. Bibcode:2013PLoSO...862737C. doi:10.1371/journal.pone.0062737. PMC 3652813. PMID 23675423.
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