Chemistry:Mechano growth factor

Mechano growth factor
Identifiers
	IUPAC name (2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S)-4-amino-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoic acid;
PubChem CID	175675731;
Chemical and physical data
Formula	C121H199N41O40
Molar mass	2868.170 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]([C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]3CCCN3C(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)O)N)O;
	InChI InChI=1S/C121H199N41O40/c1-60(166)93(158-108(191)80(55-89(130)173)153-101(184)68(23-8-12-44-123)146-107(190)79(54-88(129)172)155-115(198)95(62(3)168)160-111(194)83(59-165)157-112(195)84-29-18-50-161(84)117(200)85-30-19-51-162(85)116(199)76(36-40-87(128)171)151-96(179)66(126)52-64-31-33-65(169)34-32-64)113(196)150-69(24-9-13-45-124)102(185)156-82(58-164)109(192)149-73(35-39-86(127)170)103(186)144-71(27-16-48-138-120(133)134)99(182)143-70(26-15-47-137-119(131)132)98(181)142-67(22-7-11-43-122)97(180)140-56-90(174)141-81(57-163)110(193)159-94(61(2)167)114(197)154-78(53-63-20-5-4-6-21-63)106(189)148-75(38-42-92(177)178)105(188)147-74(37-41-91(175)176)104(187)145-72(28-17-49-139-121(135)136)100(183)152-77(118(201)202)25-10-14-46-125/h4-6,20-21,31-34,60-62,66-85,93-95,163-169H,7-19,22-30,35-59,122-126H2,1-3H3,(H2,127,170)(H2,128,171)(H2,129,172)(H2,130,173)(H,140,180)(H,141,174)(H,142,181)(H,143,182)(H,144,186)(H,145,187)(H,146,190)(H,147,188)(H,148,189)(H,149,192)(H,150,196)(H,151,179)(H,152,183)(H,153,184)(H,154,197)(H,155,198)(H,156,185)(H,157,195)(H,158,191)(H,159,193)(H,160,194)(H,175,176)(H,177,178)(H,201,202)(H4,131,132,137)(H4,133,134,138)(H4,135,136,139)/t60-,61-,62-,66+,67+,68+,69+,70+,71+,72+,73+,74+,75+,76+,77+,78+,79+,80+,81+,82+,83+,84+,85+,93+,94+,95+/m1/s1; Key:TXMSCWQMYNJNDC-XGJLPCLZSA-N;

Mechano growth factor (MGF, IGF-IEc) is a naturally occurring 24-amino acid peptide which is the C-terminal fragment derived from enzymatic cleavage of insulin-like growth factor 1 (IGF-1). It is expressed during muscle repair following physical activity, and has anabolic effects.^[1]^[2]^[3]^[4]^[5]^[6]^[7] This has led to illicit use by athletes leading to MGF being banned by the World Anti-Doping Association,^[8]^[9]^[10] and concerns have been raised about potential tumor promoting activity.^[11]

Structure and variations

The amino acid sequence is reasonably highly conserved among mammalian species, with the native human sequence being YQPPSTNKNTKSQRRKGSTFEERK or Tyr‑Gln‑Pro‑Pro‑Ser‑Thr‑Asn‑Lys‑Asn‑Thr‑Lys‑Ser‑Gln‑Arg‑Arg‑Lys‑Gly‑Ser‑Thr‑Phe‑Glu‑Glu‑Arg‑Lys. However, there are also several other splice variants of IGF-1 aside from MGF.^[12] Multiple forms of MGF are used in scientific research such as the native mouse or rat form which have several amino acid changes, or a consensus sequence mainly based on the human sequence but with the arginine changed to histidine at position 23 and sometimes other substitutions, to more closely resemble the rodent version. Since mechano growth factor is rapidly metabolised in vivo, synthetic versions often use two or more unnatural D-amino acids in the central "QRRK" portion at positions 13-16, as well as sometimes at the N-terminal tyrosine, to improve metabolic stability, and the tyrosine OH can also be PEGylated.^[13]^[14]^[15]

References

↑ "Changes in muscle mass and phenotype and the expression of autocrine and systemic growth factors by muscle in response to stretch and overload". Journal of Anatomy 194 (Pt 3): 323–334. April 1999. doi:10.1046/j.1469-7580.1999.19430323.x. PMID 10386770.
↑ "Age-related loss of skeletal muscle function; impairment of gene expression". Journal of Musculoskeletal & Neuronal Interactions 4 (2): 143–147. June 2004. PMID 15615114.
↑ "Signal transduction pathways that regulate muscle growth". Essays in Biochemistry 44: 99–108. 2008. doi:10.1042/BSE0440099. PMID 18384285.
↑ "Minireview: Mechano-growth factor: a putative product of IGF-I gene expression involved in tissue repair and regeneration". Endocrinology 151 (3): 865–875. March 2010. doi:10.1210/en.2009-1217. PMID 20130113.
↑ "Mechano-Growth Factor: an important cog or a loose screw in the repair machinery?". Frontiers in Endocrinology 3: 131. 2012. doi:10.3389/fendo.2012.00131. PMID 23125840.
↑ "Skeletal muscle hypertrophy and regeneration: interplay between the myogenic regulatory factors (MRFs) and insulin-like growth factors (IGFs) pathways". Cellular and Molecular Life Sciences 70 (21): 4117–4130. November 2013. doi:10.1007/s00018-013-1330-4. PMID 23552962.
↑ "The Roles of IGF-1 and MGF on Nerve Regeneration under Hypoxia- Ischemia, Inflammation, Oxidative Stress, and Physical Trauma". Current Protein & Peptide Science 24 (2): 143–155. 2023. doi:10.2174/1389203724666221208145549. PMID 36503467.
↑ "Therapeutic use of growth factors in the musculoskeletal system in sports-related injuries". The Journal of Sports Medicine and Physical Fitness 49 (4): 346–357. December 2009. PMID 20087293.
↑ "Mass spectrometric characterization of a biotechnologically produced full-length mechano growth factor (MGF) relevant for doping controls". Growth Hormone & IGF Research 24 (6): 276–280. December 2014. doi:10.1016/j.ghir.2014.10.004. PMID 25466910.
↑ "Detection and in vitro metabolism of the confiscated peptides BPC 157 and MGF R23H". Drug Testing and Analysis 9 (10): 1490–1498. October 2017. doi:10.1002/dta.2152. PMID 28035768.
↑ "Role of Alternatively Spliced Messenger RNA (mRNA) Isoforms of the Insulin-Like Growth Factor 1 (IGF1) in Selected Human Tumors". International Journal of Molecular Sciences 21 (19): 6995. September 2020. doi:10.3390/ijms21196995. PMID 32977489.
↑ "Biological activity of the e domain of the IGF-1Ec as addressed by synthetic peptides". Hormones 13 (2): 182–196. 2014. doi:10.1007/BF03401333. PMID 24776619.
↑ "A strong neuroprotective effect of the autonomous C-terminal peptide of IGF-1 Ec (MGF) in brain ischemia". FASEB Journal 19 (13): 1896–1898. November 2005. doi:10.1096/fj.05-3786fje. PMID 16144956.
↑ "The E-domain region of mechano-growth factor inhibits cellular apoptosis and preserves cardiac function during myocardial infarction". Molecular and Cellular Biochemistry 381 (1–2): 69–83. September 2013. doi:10.1007/s11010-013-1689-4. PMID 23712705.
↑ "Mechano growth factor, a splice variant of IGF-1, promotes neurogenesis in the aging mouse brain". Molecular Brain 10 (1). July 2017. doi:10.1186/s13041-017-0304-0. PMID 28683812.

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Original source: https://en.wikipedia.org/wiki/Mechano growth factor. Read more

[1] "Changes in muscle mass and phenotype and the expression of autocrine and systemic growth factors by muscle in response to stretch and overload". Journal of Anatomy 194 (Pt 3): 323–334. April 1999. doi:10.1046/j.1469-7580.1999.19430323.x. PMID 10386770.

[2] "Age-related loss of skeletal muscle function; impairment of gene expression". Journal of Musculoskeletal & Neuronal Interactions 4 (2): 143–147. June 2004. PMID 15615114.

[3] "Signal transduction pathways that regulate muscle growth". Essays in Biochemistry 44: 99–108. 2008. doi:10.1042/BSE0440099. PMID 18384285.

[4] "Minireview: Mechano-growth factor: a putative product of IGF-I gene expression involved in tissue repair and regeneration". Endocrinology 151 (3): 865–875. March 2010. doi:10.1210/en.2009-1217. PMID 20130113.

[5] "Mechano-Growth Factor: an important cog or a loose screw in the repair machinery?". Frontiers in Endocrinology 3: 131. 2012. doi:10.3389/fendo.2012.00131. PMID 23125840.

[6] "Skeletal muscle hypertrophy and regeneration: interplay between the myogenic regulatory factors (MRFs) and insulin-like growth factors (IGFs) pathways". Cellular and Molecular Life Sciences 70 (21): 4117–4130. November 2013. doi:10.1007/s00018-013-1330-4. PMID 23552962.

[7] "The Roles of IGF-1 and MGF on Nerve Regeneration under Hypoxia- Ischemia, Inflammation, Oxidative Stress, and Physical Trauma". Current Protein & Peptide Science 24 (2): 143–155. 2023. doi:10.2174/1389203724666221208145549. PMID 36503467.

[8] "Therapeutic use of growth factors in the musculoskeletal system in sports-related injuries". The Journal of Sports Medicine and Physical Fitness 49 (4): 346–357. December 2009. PMID 20087293.

[9] "Mass spectrometric characterization of a biotechnologically produced full-length mechano growth factor (MGF) relevant for doping controls". Growth Hormone & IGF Research 24 (6): 276–280. December 2014. doi:10.1016/j.ghir.2014.10.004. PMID 25466910.

[10] "Detection and in vitro metabolism of the confiscated peptides BPC 157 and MGF R23H". Drug Testing and Analysis 9 (10): 1490–1498. October 2017. doi:10.1002/dta.2152. PMID 28035768.

[11] "Role of Alternatively Spliced Messenger RNA (mRNA) Isoforms of the Insulin-Like Growth Factor 1 (IGF1) in Selected Human Tumors". International Journal of Molecular Sciences 21 (19): 6995. September 2020. doi:10.3390/ijms21196995. PMID 32977489.

[12] "Biological activity of the e domain of the IGF-1Ec as addressed by synthetic peptides". Hormones 13 (2): 182–196. 2014. doi:10.1007/BF03401333. PMID 24776619.

[13] "A strong neuroprotective effect of the autonomous C-terminal peptide of IGF-1 Ec (MGF) in brain ischemia". FASEB Journal 19 (13): 1896–1898. November 2005. doi:10.1096/fj.05-3786fje. PMID 16144956.

[14] "The E-domain region of mechano-growth factor inhibits cellular apoptosis and preserves cardiac function during myocardial infarction". Molecular and Cellular Biochemistry 381 (1–2): 69–83. September 2013. doi:10.1007/s11010-013-1689-4. PMID 23712705.

[15] "Mechano growth factor, a splice variant of IGF-1, promotes neurogenesis in the aging mouse brain". Molecular Brain 10 (1). July 2017. doi:10.1186/s13041-017-0304-0. PMID 28683812.

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Identifiers

IUPAC name (2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S)-4-amino-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoic acid
PubChem CID	175675731
Chemical and physical data
Formula	C₁₂₁H₁₉₉N₄₁O₄₀
Molar mass	2868.170 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@H]([C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]3CCCN3C(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)O)N)O
InChI InChI=1S/C121H199N41O40/c1-60(166)93(158-108(191)80(55-89(130)173)153-101(184)68(23-8-12-44-123)146-107(190)79(54-88(129)172)155-115(198)95(62(3)168)160-111(194)83(59-165)157-112(195)84-29-18-50-161(84)117(200)85-30-19-51-162(85)116(199)76(36-40-87(128)171)151-96(179)66(126)52-64-31-33-65(169)34-32-64)113(196)150-69(24-9-13-45-124)102(185)156-82(58-164)109(192)149-73(35-39-86(127)170)103(186)144-71(27-16-48-138-120(133)134)99(182)143-70(26-15-47-137-119(131)132)98(181)142-67(22-7-11-43-122)97(180)140-56-90(174)141-81(57-163)110(193)159-94(61(2)167)114(197)154-78(53-63-20-5-4-6-21-63)106(189)148-75(38-42-92(177)178)105(188)147-74(37-41-91(175)176)104(187)145-72(28-17-49-139-121(135)136)100(183)152-77(118(201)202)25-10-14-46-125/h4-6,20-21,31-34,60-62,66-85,93-95,163-169H,7-19,22-30,35-59,122-126H2,1-3H3,(H2,127,170)(H2,128,171)(H2,129,172)(H2,130,173)(H,140,180)(H,141,174)(H,142,181)(H,143,182)(H,144,186)(H,145,187)(H,146,190)(H,147,188)(H,148,189)(H,149,192)(H,150,196)(H,151,179)(H,152,183)(H,153,184)(H,154,197)(H,155,198)(H,156,185)(H,157,195)(H,158,191)(H,159,193)(H,160,194)(H,175,176)(H,177,178)(H,201,202)(H4,131,132,137)(H4,133,134,138)(H4,135,136,139)/t60-,61-,62-,66+,67+,68+,69+,70+,71+,72+,73+,74+,75+,76+,77+,78+,79+,80+,81+,82+,83+,84+,85+,93+,94+,95+/m1/s1 Key:TXMSCWQMYNJNDC-XGJLPCLZSA-N

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