Polylysine - Revision history

Materialscientist: Reverted edits by 1.55.255.189 (talk) (HG) (3.4.12)

2023-02-19T09:21:15Z

Reverted edits by 1.55.255.189 (talk) (HG) (3.4.12)

← Previous revision		Revision as of 09:21, 19 February 2023
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	\| ImageFile = polylysine.png		\| ImageFile = polylysine.png
	\| ImageName = Skeletal formula of ε-polylysine		\| ImageName = Skeletal formula of ε-polylysine
	\| IUPACName = ~~Polylysine~~		\| IUPACName = Poly[imino[(2''S'')-2-amino-1-oxo-1,6-hexanediyl
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}

1.55.255.189 at 08:54, 19 February 2023

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	\| ImageFile = polylysine.png		\| ImageFile = polylysine.png
	\| ImageName = Skeletal formula of ε-polylysine		\| ImageName = Skeletal formula of ε-polylysine
	\| IUPACName = ~~Poly[imino[(2''S'')-2-amino-1-oxo-1,6-hexanediyl~~		\| IUPACName = Polylysine
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}

Citation bot: Add: s2cid, doi, pages, issue, volume, journal, title, year, pmid, authors 1-6. Changed bare reference to CS1/2. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by BorgQueen | Category:Chemicals that do not have a ChemSpider ID assigned | #UCB_Category 7/851

2022-11-26T19:25:36Z

Add: s2cid, doi, pages, issue, volume, journal, title, year, pmid, authors 1-6. Changed bare reference to CS1/2. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by BorgQueen | Category:Chemicals that do not have a ChemSpider ID assigned | #UCB_Category 7/851

← Previous revision		Revision as of 19:25, 26 November 2022
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	\|-		\|-
	! Mixed		! Mixed
			\| dendric/branched polylysine — studied for RNA delivery<ref>{{cite journal \| pmid=17373579 \| year=2007 \| last1=Eom \| first1=K. D. \| last2=Park \| first2=S. M. \| last3=Tran \| first3=H. D. \| last4=Kim \| first4=M. S. \| last5=Yu \| first5=R. N. \| last6=Yoo \| first6=H. \| title=Dendritic alpha,epsilon-poly(L-lysine)s as delivery agents for antisense oligonucleotides \| journal=Pharmaceutical Research \| volume=24 \| issue=8 \| pages=1581–1589 \| doi=10.1007/s11095-006-9231-y \| s2cid=43190567 }}</ref>
	\| dendric/branched polylysine — studied for RNA delivery<ref>{{PMID\|17373579}}</ref>
	\| colspan=2 \| unheard of		\| colspan=2 \| unheard of
	\|}		\|}
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	== Polylysine in drug delivery ==		== Polylysine in drug delivery ==
	Polylysine exhibits high positive charge density which allows it to form soluble complexes with negatively charged [[macromolecule]]s.<ref>{{Cite journal\|~~last~~=Park\|~~first~~=Tae Gwan\|last2=Jeong\|first2=Ji Hoon\|last3=Kim\|first3=Sung Wan\|date=2006-07-07\|title=Current status of polymeric gene delivery systems\|journal=Advanced Drug Delivery Reviews\|volume=58\|issue=4\|pages=467–486\|doi=10.1016/j.addr.2006.03.007\|issn=0169-409X\|pmid=16781003}}</ref> Polylysine homopolymers or block copolymers have been widely used for delivery of DNA<ref>{{Cite journal\|~~last~~=Kadlecova\|~~first~~=Zuzana\|last2=Rajendra\|first2=Yashas\|last3=Matasci\|first3=Mattia\|last4=Baldi\|first4=Lucia\|last5=Hacker\|first5=David L.\|last6=Wurm\|first6=Florian M.\|last7=Klok\|first7=Harm-Anton\|date=2013-08-10\|title=DNA delivery with hyperbranched polylysine: a comparative study with linear and dendritic polylysine\|journal=Journal of Controlled Release\|volume=169\|issue=3\|pages=276–288\|doi=10.1016/j.jconrel.2013.01.019\|issn=1873-4995\|pmid=23379996}}</ref> and proteins.<ref>{{Cite journal\|~~last~~=Jiang\|~~first~~=Yuhang\|last2=Arounleut\|first2=Phonepasong\|last3=Rheiner\|first3=Steven\|last4=Bae\|first4=Younsoo\|last5=Kabanov\|first5=Alexander V.\|last6=Milligan\|first6=Carol\|last7=Manickam\|first7=Devika S.\|date=2016-06-10\|title=SOD1 nanozyme with reduced toxicity and MPS accumulation\|journal=Journal of Controlled Release\|volume=231\|pages=38–49\|doi=10.1016/j.jconrel.2016.02.038\|issn=1873-4995\|pmid=26928528}}</ref> Polylysine-based [[nanoparticle]]s have also been shown to passively accumulate in the injured sites of [[Blood vessel\|blood vessels]] after [[stroke]] due to incorporation into newly formed [[thrombus]],<ref>{{Cite journal\|~~last~~=Jiang\|~~first~~=Yuhang\|last2=Brynskikh\|first2=Anna M.\|last3=S-Manickam\|first3=Devika\|last4=Kabanov\|first4=Alexander V.\|date=2015-09-10\|title=SOD1 nanozyme salvages ischemic brain by locally protecting cerebral vasculature\|journal=Journal of Controlled Release\|volume=213\|pages=36–44\|doi=10.1016/j.jconrel.2015.06.021\|issn=1873-4995\|pmc=4684498\|pmid=26093094}}</ref> which offers a new way to deliver therapeutic agents specifically to the sites of injury after vascular damage.		Polylysine exhibits high positive charge density which allows it to form soluble complexes with negatively charged [[macromolecule]]s.<ref>{{Cite journal\|last1=Park\|first1=Tae Gwan\|last2=Jeong\|first2=Ji Hoon\|last3=Kim\|first3=Sung Wan\|date=2006-07-07\|title=Current status of polymeric gene delivery systems\|journal=Advanced Drug Delivery Reviews\|volume=58\|issue=4\|pages=467–486\|doi=10.1016/j.addr.2006.03.007\|issn=0169-409X\|pmid=16781003}}</ref> Polylysine homopolymers or block copolymers have been widely used for delivery of DNA<ref>{{Cite journal\|last1=Kadlecova\|first1=Zuzana\|last2=Rajendra\|first2=Yashas\|last3=Matasci\|first3=Mattia\|last4=Baldi\|first4=Lucia\|last5=Hacker\|first5=David L.\|last6=Wurm\|first6=Florian M.\|last7=Klok\|first7=Harm-Anton\|date=2013-08-10\|title=DNA delivery with hyperbranched polylysine: a comparative study with linear and dendritic polylysine\|journal=Journal of Controlled Release\|volume=169\|issue=3\|pages=276–288\|doi=10.1016/j.jconrel.2013.01.019\|issn=1873-4995\|pmid=23379996}}</ref> and proteins.<ref>{{Cite journal\|last1=Jiang\|first1=Yuhang\|last2=Arounleut\|first2=Phonepasong\|last3=Rheiner\|first3=Steven\|last4=Bae\|first4=Younsoo\|last5=Kabanov\|first5=Alexander V.\|last6=Milligan\|first6=Carol\|last7=Manickam\|first7=Devika S.\|date=2016-06-10\|title=SOD1 nanozyme with reduced toxicity and MPS accumulation\|journal=Journal of Controlled Release\|volume=231\|pages=38–49\|doi=10.1016/j.jconrel.2016.02.038\|issn=1873-4995\|pmid=26928528}}</ref> Polylysine-based [[nanoparticle]]s have also been shown to passively accumulate in the injured sites of [[Blood vessel\|blood vessels]] after [[stroke]] due to incorporation into newly formed [[thrombus]],<ref>{{Cite journal\|last1=Jiang\|first1=Yuhang\|last2=Brynskikh\|first2=Anna M.\|last3=S-Manickam\|first3=Devika\|last4=Kabanov\|first4=Alexander V.\|date=2015-09-10\|title=SOD1 nanozyme salvages ischemic brain by locally protecting cerebral vasculature\|journal=Journal of Controlled Release\|volume=213\|pages=36–44\|doi=10.1016/j.jconrel.2015.06.021\|issn=1873-4995\|pmc=4684498\|pmid=26093094}}</ref> which offers a new way to deliver therapeutic agents specifically to the sites of injury after vascular damage.

	==Chemical modification==		==Chemical modification==

Beland: convert special characters found by Wikipedia:Typo Team/moss (via WP:JWB)

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	}}		}}

	'''Polylysine''' refers to several types of [[lysine]] [[homopolymer]]s, which may differ from each other in terms of stereochemistry (D/L; the L form is natural and usually assumed) and link position (~~α~~/~~ε~~). Of these types, only ε-poly-L-lysine is produced naturally.		'''Polylysine''' refers to several types of [[lysine]] [[homopolymer]]s, which may differ from each other in terms of stereochemistry (D/L; the L form is natural and usually assumed) and link position (α/ε). Of these types, only ε-poly-L-lysine is produced naturally.

	==Chemical structure==		==Chemical structure==
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	!! !! L !! D !! Mixed		!! !! L !! D !! Mixed
	\|-		\|-
	! ~~α~~		! α
	\| poly-<small>L</small>-lysine (PLL) — coating		\| poly-<small>L</small>-lysine (PLL) — coating
	\| poly-<small>D</small>-lysine (PDL) — coating		\| poly-<small>D</small>-lysine (PDL) — coating
	\| synthesized, no applications		\| synthesized, no applications
	\|-		\|-
			! ε
	! ε
	\| ε-polylysine, EPL — natural antibacterial		\| ε-polylysine, EPL — natural antibacterial
	\| colspan=2 \| unheard of		\| colspan=2 \| unheard of
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	Production of polylysine by natural fermentation is only observed in strains of bacteria in the genus ''[[Streptomyces]]''. ''[[Streptomyces albulus]]'' is most often used in scientific studies and is also used for the commercial production of ε-polylysine.		Production of polylysine by natural fermentation is only observed in strains of bacteria in the genus ''[[Streptomyces]]''. ''[[Streptomyces albulus]]'' is most often used in scientific studies and is also used for the commercial production of ε-polylysine.

	α-Polylysine is synthetically produced by a basic [[Condensation polymer\|polycondensation]] reaction.<ref>{{Cite web \| url=http://www.alamanda-polymers.com/content/poly-l-lysine-and-poly-d-lysine \| title=Poly-L-Lysine and Poly-D-Lysine ~~\|~~ Alamanda Polymers - Polyamino Acids, Superior by Design}}</ref>		α-Polylysine is synthetically produced by a basic [[Condensation polymer\|polycondensation]] reaction.<ref>{{Cite web \| url=http://www.alamanda-polymers.com/content/poly-l-lysine-and-poly-d-lysine \| title=Poly-L-Lysine and Poly-D-Lysine {{pipe}} Alamanda Polymers - Polyamino Acids, Superior by Design}}</ref>

	==History==		==History==

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	==Chemical structure==		==Chemical structure==
	{{missing information\|section\|DL mixed (alpha)-poly-DL-lysine — seems to have some use involving copper}}		{{missing information\|section\|DL mixed (alpha)-poly-DL-lysine — seems to have some use involving copper\|date=October 2022}}
	The precursor amino acid lysine contains two [[amino group]]s, one at the [[Alpha and beta carbon#Proteins and amino acids\|α-carbon]] and one at the ε-carbon. Either can be the location of [[polymerization]], resulting in α-polylysine or ε-polylysine. Polylysine is a homopolypeptide belonging to the group of [[cationic]] [[polymer]]s: at [[pH]] 7, polylysine contains a positively charged [[hydrophilic]] amino group.		The precursor amino acid lysine contains two [[amino group]]s, one at the [[Alpha and beta carbon#Proteins and amino acids\|α-carbon]] and one at the ε-carbon. Either can be the location of [[polymerization]], resulting in α-polylysine or ε-polylysine. Polylysine is a homopolypeptide belonging to the group of [[cationic]] [[polymer]]s: at [[pH]] 7, polylysine contains a positively charged [[hydrophilic]] amino group.

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	==History==		==History==
	{{missing information\|section\|other variants}}		{{missing information\|section\|other variants\|date=October 2022}}
	The production of ε-polylysine by natural fermentation was first described by researchers Shoji Shima and Heiichi Sakai in 1977.<ref name="Shima"/> Since the late 1980s, ε-polylysine has been approved by the Japanese [[Ministry of Health, Labour and Welfare]] as a preservative in food. In January 2004, ε-polylysine became [[generally recognized as safe]] (GRAS) certified in the United States.<ref name="FDA">[http://www.cfsan.fda.gov/~rdb/opa-g135.html GRAS Notice No. GRN 000135] {{webarchive\|url=https://web.archive.org/web/20080511163336/http://www.cfsan.fda.gov/~rdb/opa-g135.html \|date=2008-05-11 }}</ref>		The production of ε-polylysine by natural fermentation was first described by researchers Shoji Shima and Heiichi Sakai in 1977.<ref name="Shima"/> Since the late 1980s, ε-polylysine has been approved by the Japanese [[Ministry of Health, Labour and Welfare]] as a preservative in food. In January 2004, ε-polylysine became [[generally recognized as safe]] (GRAS) certified in the United States.<ref name="FDA">[http://www.cfsan.fda.gov/~rdb/opa-g135.html GRAS Notice No. GRN 000135] {{webarchive\|url=https://web.archive.org/web/20080511163336/http://www.cfsan.fda.gov/~rdb/opa-g135.html \|date=2008-05-11 }}</ref>

Artoria2e5 at 16:48, 14 October 2022

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	\|-		\|-
	! Mixed		! Mixed
	\| dendric polylysine — studied for RNA delivery<ref>{{PMID\|17373579}}</ref>		\| dendric/branched polylysine — studied for RNA delivery<ref>{{PMID\|17373579}}</ref>
	\| colspan=2 \| unheard of		\| colspan=2 \| unheard of
	\|}		\|}

Artoria2e5 at 16:47, 14 October 2022

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← Previous revision		Revision as of 16:47, 14 October 2022
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	}}		}}

	'''Polylysine''' refers to several types of [[lysine]] [[homopolymer]]s, which may differ from each other in terms of stereochemistry (D/L; the L form is natural and usually assumed) and link position (α/ε). Of these types, only ε-poly-L-lysine ~~(usually just ε-polylysine)~~ is produced naturally.		'''Polylysine''' refers to several types of [[lysine]] [[homopolymer]]s, which may differ from each other in terms of stereochemistry (D/L; the L form is natural and usually assumed) and link position (α/ε). Of these types, only ε-poly-L-lysine is produced naturally.

	==Chemical structure==		==Chemical structure==

Artoria2e5 at 16:46, 14 October 2022

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	Polylysine has a light yellow appearance and is slightly bitter in taste whether in powder or liquid form.		Polylysine has a light yellow appearance and is slightly bitter in taste whether in powder or liquid form.

	==Polylysine ~~in tissue culture~~==		== α-Polylysine==
			===In tissue culture===
	α-Polylysine is commonly used to coat tissue cultureware as an attachment factor which improves cell adherence. This phenomenon is based on the interaction between the positively charged polymer and negatively charged cells or proteins. While the poly-<small>L</small>-lysine (PLL) precursor amino acid occurs naturally, the poly-<small>D</small>-lysine (PDL) precursor is an artificial product. The latter is therefore thought to be resistant to enzymatic degradation and so may prolong cell adherence.<ref>{{cite journal \| doi = 10.1083/jcb.66.1.198 \| author = Mazia, D.\| year = 1975 \| title = Adhesion of cells to surfaces coated with polylysine. Applications to electron microscopy. \| journal = The Journal of Cell Biology \| volume = 66 \| pages = 198–200 \| pmid = 1095595 \| issue = 1\|display-authors=etal \| pmc=2109515}}</ref>		α-Polylysine is commonly used to coat tissue cultureware as an attachment factor which improves cell adherence. This phenomenon is based on the interaction between the positively charged polymer and negatively charged cells or proteins. While the poly-<small>L</small>-lysine (PLL) precursor amino acid occurs naturally, the poly-<small>D</small>-lysine (PDL) precursor is an artificial product. The latter is therefore thought to be resistant to enzymatic degradation and so may prolong cell adherence.<ref>{{cite journal \| doi = 10.1083/jcb.66.1.198 \| author = Mazia, D.\| year = 1975 \| title = Adhesion of cells to surfaces coated with polylysine. Applications to electron microscopy. \| journal = The Journal of Cell Biology \| volume = 66 \| pages = 198–200 \| pmid = 1095595 \| issue = 1\|display-authors=etal \| pmc=2109515}}</ref>

Artoria2e5 at 16:46, 14 October 2022

2022-10-14T16:46:24Z

← Previous revision		Revision as of 16:46, 14 October 2022
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	The production of ε-polylysine by natural fermentation was first described by researchers Shoji Shima and Heiichi Sakai in 1977.<ref name="Shima"/> Since the late 1980s, ε-polylysine has been approved by the Japanese [[Ministry of Health, Labour and Welfare]] as a preservative in food. In January 2004, ε-polylysine became [[generally recognized as safe]] (GRAS) certified in the United States.<ref name="FDA">[http://www.cfsan.fda.gov/~rdb/opa-g135.html GRAS Notice No. GRN 000135] {{webarchive\|url=https://web.archive.org/web/20080511163336/http://www.cfsan.fda.gov/~rdb/opa-g135.html \|date=2008-05-11 }}</ref>		The production of ε-polylysine by natural fermentation was first described by researchers Shoji Shima and Heiichi Sakai in 1977.<ref name="Shima"/> Since the late 1980s, ε-polylysine has been approved by the Japanese [[Ministry of Health, Labour and Welfare]] as a preservative in food. In January 2004, ε-polylysine became [[generally recognized as safe]] (GRAS) certified in the United States.<ref name="FDA">[http://www.cfsan.fda.gov/~rdb/opa-g135.html GRAS Notice No. GRN 000135] {{webarchive\|url=https://web.archive.org/web/20080511163336/http://www.cfsan.fda.gov/~rdb/opa-g135.html \|date=2008-05-11 }}</ref>

	==Polylysine ~~in food~~==		== ε-Polylysine==
			===In food===
	ε-Polylysine is used commercially as a food [[preservative]] in Japan, Korea and in imported items sold in the United States. Food products containing polylysine are mainly found in Japan. The use of polylysine is common in food applications such as boiled rice, cooked vegetables, soups, [[noodles]] and sliced fish ([[sushi]]).<ref name="Hiraki">{{cite journal \| doi = 10.1016/S0273-2300(03)00029-1 \| author = Hiraki, J.\| year = 2003 \| title = Use of ADME studies to confirm the safety of ε-polylysine as a preservative in food \| journal = [[Regulatory Toxicology and Pharmacology]] \| volume = 37 \| pages = 328–340 \| pmid = 12726761 \| issue = 2\|display-authors=etal}}</ref>		ε-Polylysine is used commercially as a food [[preservative]] in Japan, Korea and in imported items sold in the United States. Food products containing polylysine are mainly found in Japan. The use of polylysine is common in food applications such as boiled rice, cooked vegetables, soups, [[noodles]] and sliced fish ([[sushi]]).<ref name="Hiraki">{{cite journal \| doi = 10.1016/S0273-2300(03)00029-1 \| author = Hiraki, J.\| year = 2003 \| title = Use of ADME studies to confirm the safety of ε-polylysine as a preservative in food \| journal = [[Regulatory Toxicology and Pharmacology]] \| volume = 37 \| pages = 328–340 \| pmid = 12726761 \| issue = 2\|display-authors=etal}}</ref>

Artoria2e5: /* Chemical structure */

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Chemical structure

@@ Line 26: / Line 26: @@
 '''Polylysine''' refers to several types of [[lysine]] [[homopolymer]]s, which may differ from each other in terms of stereochemistry (D/L; the L form is natural and usually assumed) and link position (&alpha;/&epsilon;). Of these types, only ε-poly-L-lysine (usually just ε-polylysine) is produced naturally.
-==Chemical structure and function==
+==Chemical structure==
 {{missing information|section|DL mixed (alpha)-poly-DL-lysine — seems to have some use involving copper}}
 The precursor amino acid lysine contains two [[amino group]]s, one at the [[Alpha and beta carbon#Proteins and amino acids|α-carbon]] and one at the ε-carbon. Either can be the location of [[polymerization]], resulting in α-polylysine or ε-polylysine. Polylysine is a homopolypeptide belonging to the group of [[cationic]] [[polymer]]s: at [[pH]] 7, polylysine contains a positively charged [[hydrophilic]] amino group.
@@ Line 35: / Line 35: @@
 ε-Polylysine (ε-poly-<small>L</small>-lysine, EPL) is typically produced as a homopolypeptide of approximately 25–30 <small>L</small>-lysine residues.<ref name="Shima">{{cite journal | author = Shima, S. and Sakai H. | year = 1977 | title = Polylysine produced by Streptomyces | journal = Agricultural and Biological Chemistry | volume = 41 | issue = 9 | pages = 1807–1809 | doi=10.1271/bbb1961.41.1807| doi-access = free }}</ref> According to  research, ε-polylysine is adsorbed electrostatically to the cell surface of the bacteria, followed by a stripping of the [[Bacterial outer membrane|outer membrane]]. This eventually leads to the abnormal distribution of the [[cytoplasm]] causing damage to the bacterial cell<ref>{{cite journal | author = Shima, S.| year = 1984 | title = Antimicrobial action of ε-poly-L-lysine | journal = Journal of Antibiotics | volume = 37 | pages = 1449–1455 | pmid = 6392269 | issue = 11 | doi=10.7164/antibiotics.37.1449|display-authors=etal| doi-access = free }}</ref> that is produced by bacterial fermentation. ε-Poly-<small>L</small>-lysine is used as a natural preservative in food products.
 ==Production==