Testosterone Hydrophilic

by Benjamin Bunting BA(Hons) PGCert

ben bunting BA(Hons) PgCert Sport & Exercise Nutriton  Written by Ben Bunting: BA(Hons), PGCert. Sport & Exercise Nutrition. L2 Strength & Conditioning Coach.

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Hydrophilic Explained

The word hydrophilic comes from the prefix "hydro" and a noun meaning "water." As you can imagine, everything we use on a daily basis is derived from water. Similarly, everything in nature relies on water. This property helps things like proteins, nutrients, and cell membrane components to travel easily through the blood. Hydrophilic substances are common in everyday objects, including table salt, shampoo, and laundry detergent.

In fact, water-loving materials attract water and hold on to that state for longer than hydrophobic counterparts. For example, coatings of rubber with hydrophilic materials increase the sealing power of the material and prevent water leaks. They also improve the visibility of the tape, ensuring that it remains legible and recognizable. Hydrophilic materials also have many other applications, which can be described as "water-loving".

Wet surfaces can be classified according to their wettability. The degree to which they attract water depends on the contact angle. The contact angle is the distance between the edge of a droplet and the surface. If the contact angle is less than 90 degrees, a liquid is considered to be hydrophilic. Conversely, if the contact angle is greater than 90 degrees, a liquid is hydrophobic. So, to understand how these differences affect surfaces, you can apply the principles of surface science to understand and designate your materials.

What is a hydrophilic substance? Hydrophilic materials have strong hydrogen-bonding abilities, and they are highly soluble in polar solvents. Water is an excellent solvent in many situations, and the hydrophilic properties of hydrophobic materials are often used to keep an area clean. In industry, for example, hydrophilic membranes are highly attractive to water. In this way, water molecules can push away contaminants and keep them from clogging up the membrane.

Are Steroid Hormones Hydrophilic?

Steroid hormones are hydrophobic and are not soluble in water. Steroid hormones act on the central nervous system and peripheral target tissues. Depending on their structure, they can either diffuse out of the cell or rebind to receptors. This explains the importance of understanding the structure of steroid hormones.

Many hormones travel through the bloodstream with carrier proteins that increase their solubility in water. Carrier proteins include albumin, corticosteroid-binding globulin, and sex hormone-binding globulin. Because they're hydrophilic, they can pass through cell membranes, but they still need to pass through the water-soluble cytoplasm. This is the free-hormone hypothesis.

Steroid hormones are made up of cholesterol, while peptide hormones are made up of amino acids. The difference between hydrophilic and hydrophobic hormones can be important for certain functions. Steroid hormones can diffuse through the cell membrane by dissociation of its plasma carrier protein, whereas peptide hormones have a high affinity for protein-bound molecules and cannot pass through the membrane. In addition, peptide hormones are large and hydrophilic.

In addition to influencing gene expression in the cytoplasm, steroid hormones can directly initiate protein production within target cells. They bind to a receptor on the cell membrane, which then transports the hormone complex to the nucleus. The receptor-hormone complex then binds to a specific gene on DNA. The resulting messenger RNA is then translated into the desired protein in the cytoplasm.

Calculating if testosterone is hydrophilic

A simple way to determine whether a substance is hydrophilic is to measure its surface area by measuring the distance between the molecules and the tryptophan side chains. A stick representation of the two substances is provided in the image below. The stick representations are coloured according to the contributions of each atom to the protein surface. Testosterone's carbon atoms are shown in yellow. If the two compounds are hydrophilic, then they bind to each other.

Testosterone hydroxylation is a key step in the testosterone biosynthesis pathway. Testosterone is a large hydrophobic molecule, and the presence of intact Gram-negative cells limits its uptake by cells. Biocatalytic hydroxylation uses a self-sufficient cytochrome P450 monooxygenase BM3 from Bacillus megaterium. The biocatalysts were recombinant Escherichia coli cells, which provided a protective environment for the recombinant enzymes and ensured continuous cofactor recycling via glucose catabolism.

Using Dimethyl sulfoxide (DMSO)

One tested a library of engineered BM3 variants capable of hydroxylation of testosterone at the 2b and 15b positions. Both inhibitors and testosterone hydrophilic compounds were homologously expressed in E. coli BL21-Gold(DE3) cells. We found that the most promising variants displayed high conversion and regioselectivity. We also measured the growth rates of these mutants and determined the specific activities. These variants showed volumetric activities of up to 0.58 U L-1. We performed this study using standard E. coli cells that contain approximately 55% total protein.

Using Polydimethylsiloxane (PDMS)

The release of testosterone from polymers modified with graft copolymers was assessed using human whole blood. Using a graft copolymer, testosterone released from the polymer was significantly decreased at lower grafting and weight % PEO levels. Using a hydrophilic PDMS/PEO graft copolymer, testosterone release rates were not affected by resinous copolymer loading, but were significantly reduced at high grafting levels.

Other steroid hormones

Androstenedione

Androstenedione is a hydrophilic steroid, which is derived from the phytosterol. This steroid is produced through whole-cell biotransformation in a quaternary phosphonium salt ionic liquid cosolvent system. The hydrophilic nature of this steroid is one of the reasons why it is so popular with bodybuilders. 

Cortisol

Cortisol is an essential hormone that controls our sleep-wake cycle and regulates our metabolism. It is important for the body to have enough of this hormone, but a consistently high level of cortisol may be harmful. This hormone also suppresses inflammation. If you have chronically high cortisol levels, you may be at risk for inflammatory conditions and weakened immune system. Hence, it's important to understand how cortisol works in the body.

Cortisol is lipid soluble, which makes it difficult for it to enter the cell membrane. This makes it necessary for the corticosteroid to diffuse into the blood plasma. Cortisol is mainly bound to a protein called albumin. This makes it possible to measure free cortisol in most body fluids. However, since albumin is mostly hydrophobic, cortisol cannot pass through the cell membrane.

This hormone is produced when cholesterol is converted into cortisol. It is lipophilic enough to cross the plasma membrane. It then binds to glucocorticoid receptors on target cells. Glucocorticoid receptors are found in virtually all nucleated tissues. The receptor is located in the cytoplasm, where it interacts with another protein called a chaperone. Once bound, the GR-CHP complex moves to the nucleus.

Cortisol is a naturally occurring pregnane corticosteroid. Its scientific name is 11b,17a,21-trihydroxypregn-4-ene-3-dione. The enzymes it activates include lysyl oxidase, which crosslinks collagen and elastin. Another enzyme that Cortisol activates is superoxide dismutase, which is particularly useful in the immune system. The latter enzyme helps to destroy bacteria.

Progesterone

The female reproductive hormones Progesterone and Testosterone belong to a class of hormones known as "progestogens". They regulate ovulation, initiate milk production, and impact numerous other physiological processes. Human creativity has adapted natural progesterone for medical purposes. Progesterone and Testosterone are both fat-soluble organic compounds containing 17 carbon atoms. Progesterone is identical to testosterone except for the acetylation of the -OH group on the C-17 carbon ring.

Progesterone is a naturally occurring hormone that plays an important role in the female menstrual cycle, pregnancy, and embryogenesis. It belongs to a group of hormones called progestogens. The name progesterone is also used to describe the synthetic steroids that mimic the progesterone action. The hydrophobic nature of progesterone stems from its lack of polar groups.

In pregnancy, progesterone is essential in converting the endometrium into the secretory stage, preparing the uterus for implantation. It also affects cervical mucus and vaginal epithelium. However, progesterone is not absorbed properly when taken orally. In women who do not conceive, progesterone levels drop and menstrual bleeding occurs. This process is known as progesterone withdrawal bleeding.

To increase the bioavailability of Progesterone, the drug is formulated with micellar surfactant solutions. Surfactants with hydrophilic head groups have variable hydrophobic chains. These surfactants had the greatest effect on solubilization, whereas those without hydrophilic head groups had smaller effects. These surfactants are charged and interact with the hydrophilic residues on the receptor.

In addition to its ability to bind GABAA receptors, progesterone also binds to the GABA-A receptor. Progesterone can inhibit the GABA-A receptor and influence its function by regulating GABA-gated currents. This regulation is also involved in the progesterone's protective effect against kainate-induced seizures. Although the mechanism is not completely understood, this research will help us make better choices for treating our health problems.

DHEA

A study of rats with high levels of DHEA has shown that it is a potent atheroprotective hormone. Early studies showed that it reduced the formation of atherosclerotic plaques by 50% and aortic fatty streaks by 30%. More recently, epidemiological studies have shown a negative correlation between testosterone and DHEA levels in men over 50 years of age. This inverse relationship was attributed to the role of the IGF-1/IGFBP-1 axis in the formation of atherosclerosis. IGF-I stimulates the migration and proliferation of VSMCs through the a5b1 integrin.

Neurosteroids have been studied since the early 1980s and may one day be useful for treating neurological disorders and chronic pain. 

The hydrogen bonding between DHEA and MAP2C is mediated by two different amino acids. The His 116 and Asp 118 of the D ring are capable of forming two hydrogen bonds, while the Tyr 155 atom is not. This interaction is achieved through hydrophobic interactions and hydrogen bonding. But it's not all bad news. DHEA is a complex hormone and may have a hydrophobic molecule despite its role in human biology.

In humans, DHEA is an important androgen prohormone. When it's abundant, it may moderate the effects of aging and certain maladies. DHEA declines as people age. Endogenous DHEA has the potential to moderate aging of the central nervous system, cardiovascular system, and bones. Therapeutic DHEA has similar potential for the same purposes. In animals, DHEA supplements may slow the effects of aging and promote a more vibrant life.

DHEA has several beneficial effects on the skin. The substance stimulates sebum production. After 12 months of DHEA therapy, the index of sebum secretion increased by 79%. Three months later, the index returned to pre-treatment levels. In conclusion, DHEA has many benefits on the skin, particularly in women. The results of studies conducted by Baulieu show that DHEA has a positive effect on skin health.

Conclusion

Testosterone is a steroid hormone, and as with all steroid hormones, they are not hydrophilic and are in fact hydrophobic. In contrast, peptide hormones are hydrophilic. 

What this means is that steroid hormones such as testosterone cannot dissolve in water. As a result, steroid hormones are carried by albumin, sex hormone-binding globulin (SHBG), and corticosteroid-binding globulin (CBG) which are the transporters in the blood. 

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